IP Library › Granted Patent US 12,281,100

Granted Patent B2

US 12,281,100 · App. 16/877,336 · Granted Apr 22, 2025

Recyclable and reconfigurable high-performance polymer networks and uses thereof

Inventors: Brett A. Helms (Oakland, CA); Peter R. Christensen (Berkeley, CA)

Assignee: The Regents of the University of California

C07D403/06 C07C49/573 C07C225/24 C07D407/06 C08G73/0273 C08J5/02 C08J9/04 C08J11/28 C08K11/00 C08L79/02 C09J179/02 G10K11/162 G10K11/18 H01B1/124 H01B3/30 C08J2205/04 C08J2379/02 C08L2203/14

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Quick Facts

Patent No.: US 12,281,100
App. No.: 16/877,336
Granted: Apr 22, 2025
Kind: B2

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Abstract

The present invention relates to a composition of polymers comprising dynamic covalent diketoenamine bonds. This composition allows the formulation of polymeric materials with a wide range of architectures and properties, and further allows these materials to be recycled using thermal, chemical, or mechanical processes.

Claims (286)

1. A composition comprising a polymer, or polymer network, having at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;

wherein said polymer, or polymer network, is obtained by connecting one compound Y comprising at least two functional groups selected from the group (A), (B), (C), (D), (E), (F), (G), (H), (I), (J), (K), (L), (M), (N), (O), (P), (Q), (R), (S), (T), (U), (V), and/or (W), or a mixture thereof;

with at least one compound Z comprising at least two amine functional groups of the type —NH 2 , —NHR 4 , —NH 3 + and/or —NHR 4 R 5+ groups, or at least two functional groups that generates —NH 2 , —NHR 4 , —NH 3 + and/or —NHR 4 R 5+ in situ, or a mixture thereof;

wherein said amine is optionally (C 1-20 )alkyl, (C 2-20 )alkenyl; (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero (C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; or heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, moiety, said heteroatoms being each independently a C, Si, chalcogenide, or a pnictide;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero (C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and

heteroaryl(C 1-20 )alkyl, can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero (C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, can be unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero (C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; —NO 2 ; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 , and

wherein the ratio R is less than, or equal to 1 (R≤1), where R=(sum (functionality of compound Y (F Y )×number of moles of compound Y (N Y ))/(sum (functionality of compound Z (F Z )×number of moles of all molecules of compound Z (N Z )):

∑

⁢

∑

⁢

≤

;

wherein R 1 is selected from the group consisting of (C 1-20 )alkyl, (C 2-20 )alkenyl; (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero(C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; and heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-2 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 , —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein R 2 is selected from the group consisting of (C 1-20 )alkyl, (C 2-20 )alkenyl; (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero(C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; and heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenid), or a pnictid);

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-2 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein R 2 and R 3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 3 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is independently optionally substituted with one or more Z 2 wherein each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 , —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 , —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein R 2 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein X 1 and R 2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;

wherein X 1 and R 3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-2 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NRSS(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ,

wherein R 3 is selected from the group consisting of (C 1-20 )alkyl, (C 2-20 )alkenyl; (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero(C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; and heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

wherein each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 , and

wherein R 3 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 3 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 , —SR 5 ; —S(O)R 4 , —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O)R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4

wherein R 3 is linked to R 1 with a linker X 1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 , —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O); R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

each R 4 is independently selected from the group consisting of hydrogen, C( 1-20 )alkyl, C( 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; heterocyclyl(C 1-20 )akyl; and heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl, optionally comprise one or more heteroatoms in the alkyl, alkenyl or alkynyl moiety, said heteroatoms being each independently selected from O, S and N; and wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

each R 5 is independently selected from the group consisting of hydrogen, (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl;

each R 6 and R 7 is independently selected from the group consisting of hydrogen; (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

and wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

or wherein R 6 and R 7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.

2. A method for synthesizing a polymer from one or more precursors in one or more solvents, said method comprising:

(a) dissolving, dispersing, or suspending one or more precursors individually in the same solvent, or individually in different and/or separate solvents, optionally with one or more surfactants;

(b) optionally heating the solvent or one or more solvents of the different and/or separate solvents;

(c) mixed the solvent comprising the one or more precursors together to form a polymer; wherein said polymer has at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;

wherein said amine is optionally (C 1-20 )alkyl, (C 2-20 )alkenyl), (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 2-20 )alkyl; hetero(C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; or heteroaryl(C 1-20 )alkyl;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O);

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; can be unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen: (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 R 6 R 7 ; —NO 2 ; —NR 5 C(O)R 4 ; —NR 5 S(O)R 4 ; NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

∑

⁢

∑

⁢

≤

;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 , —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —COR 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenid), or a pnictid);

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O);

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; NR 5 C(O) 2 NR 6 R 7 ; NR 6 R 7 ; cyano; —COR 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein R 2 and R 3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 3 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is independently optionally substituted with one or more Z 2 wherein each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl(C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O)R 4 , —NR 5 C(O)NR 6 R 7 , NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein R 2 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein X 1 and R 2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;

wherein X 1 and R 3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O)R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 3 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alky); (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O);

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

wherein R 3 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 3 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 , —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 , —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein R 3 is linked to R 1 with a linker X 1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

or wherein R 6 and R 7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.

3. A method for synthesizing a polymer by melting one or more solid precursors, said method comprising:

(d) optionally mixing the one or more precursors are solids prior to, during, and/or subsequent to the melting step, or melting the precursors which are solid are optionally first melted individually then mixed together to form a polymer;

wherein optionally the melting of the one or more precursors is in a single or twin screw compound extrusion device;

wherein said polymer has at least one unit of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), and/or (XX), or a mixture thereof;

wherein said amine is optionally (C 1-20 )alkyl, (C 2-20 )alkenyl; (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero(C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; or heteroaryl(C 1-20 )alkyl;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; can be unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen: (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O)R 4 ; —SO 2 NR 6 R 7 ; —NO 2 ; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

∑

⁢

∑

⁢

≤

;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 , —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 , NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenid), or a pnictid);

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

each Z 1 is independently selected from the group consisting of halogen: (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein R 2 and R 3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 3 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is independently optionally substituted with one or more Z 2 wherein each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 ) cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 , —NR 5 C(O) NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein R 2 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein X 1 and R 2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;

wherein X 1 and R 3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 , —NR 5 C(O)NR 6 R 7 , NR 6 R 7 ; cyano; —CO 2 R 5 ; C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein R 3 is selected from the group consisting of (C 1-20 )alkyl, (C 2-20 )alkenyl; (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero (C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; and heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and

heteroaryl(C 1-20 )alkyl; is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

wherein each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl(C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O)R 4 ; —SO 2 NR 6 R 7 ; nitro; NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 , NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O) R 4 ; and

wherein R 3 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 3 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 , —SR 5 , —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 , NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4

wherein R 3 is linked to R 1 with a linker X 1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl(C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 , —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

and wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl(C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

or wherein R 6 and R 7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.

4. A method for synthesizing a polymer from one or more precursors using mechanical grinding, said method comprising:

mixing one or more said precursors together in a shaking or rotating chamber to form a polymer;

wherein said shaking or rotating chamber is optionally a ball mill,

wherein optionally said shaking or rotating chamber contains a grinding medium;

wherein said grinding medium optionally comprises of one or several sizes of spheres or rods made of metallic, composite, ceramic, or polymer materials;

wherein said precursors are optionally dissolved in a solvent prior to mechanical grinding in said rotating chamber, also optionally called a ball mill;

wherein said precursors are optionally mixed together in a solvent during mechanical grinding;

wherein if one or more precursors are solids, precursors are optionally melted together before mixing;

wherein the duration of mixing of precursors within said shaking or rotating chamber, optionally with said grinding medium, is used to control the extent of polymerization;

wherein the duration of mixing of said precursors within said shaking or rotating chamber is used to control polymer properties;

wherein said polymer properties may optionally include the glass transition temperature (T g ), polymer solubility, modulus, tensile strength, polymer color, polymer toughness, polymer rigidity;

wherein said amine is optionally (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl(C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero(C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; or heteroaryl(C 1-20 )alkyl; wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, moiety, said heteroatoms being each independently a C, Si, chalcogenide, or a pnictide;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; can optionally be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; can be unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen: (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; —NO 2 ; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 , and

∑

⁢

∑

⁢

≤

;

wherein Riis selected from the group consisting of (C 1-20 )alkyl, (C 2-20 )alkenyl; (C 2-20 )alkynyl; (C 6-12 )aryl, (C 3-8 )cycloalkyl; (C 6-12 )aryl(C 1-20 )alkyl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; hetero(C 1-20 )alkyl; heterocyclyl; heterocyclyl(C 1-20 )alkyl; heteroaryl; and heteroaryl(C 1-20 )alkyl;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictid);

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O) NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety each heteroatom is independently a C, Si, chalcogenid), or a pnictid);

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl(C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and/or heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

each Z 1 is independently selected from the group consisting of halogen: (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ; and

wherein R 2 and R 3 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 3 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is independently optionally substituted with one or more Z 2 wherein each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 ) cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 ) cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O)NR 6 R 7 , NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein R 2 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 2 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein X 1 and R 2 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered heterocyclyl, or heteroaryl;

wherein X 1 and R 3 are optionally directly bonded together to form a, 5, 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; NR 5 C(O)R 4 ; —NR 5 (O) 2 R 4 , —NR 5 C(O)NR 6 R 7 , NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and C(O)R 4 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

wherein at least one carbon atom or heteroatom of said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and

heteroaryl(C 1-20 )alkyl; is optionally oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl; is unsubstituted or substituted with one or more Z 1 ;

wherein each Z 1 is independently selected from the group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 6 R 7 ; nitro; —NR 5 C(O)R 4 :—NR 5 S(O) 2 R 4 ; —NR 5 C(O) NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O) 2 NR 6 R 7 ; and C(O)R 4 ; and

wherein R 3 and R 1 are optionally directly bonded together to form a, 5 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein R 3 and R 1 are optionally bonded together with a linker X 1 to form a 6, 7, or 8 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide (such as O, S, or Se), or a pnictide (such as N, or P);

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl, (C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 , —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 , —NR 5 C(O) NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 7 ; —C(O)NR 6 R 7 ; and —C(O)R 4

wherein R 3 is linked to R 1 with a linker X 1 to form a 4, 5, 6, or 7 membered cycloalkyl, heterocyclyl, or heteroaryl;

wherein X 1 within said cycloalkyl, heterocyclyl, or heteroaryl is independently selected from the group consisting of C, Si, chalcogenide, or a pnictide;

wherein each said heterocyclyl; or heteroaryl is optionally substituted with one or more Z 2 where each Z 2 is independently selected from the following group consisting of halogen; (C 1-20 )alkyl; (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 6-12 )aryl, (C 3-8 )cycloalkyl(C 6-12 )aryl(C 1-20 )alkyl, hetero(C 1-20 )alkyl; heterocyclyl; heteroaryl; (C 3-8 )cycloalkyl(C 1-20 )alkyl; heterocyclyl(C 1-20 )alkyl; heteroaryl(C 1-20 )alkyl; halo(C 1-20 )alkyl; halo(C 1-20 )alkyloxy; —OR 5 ; —SR 5 ; —S(O)R 4 ; —S(O) 2 R 4 ; —SO 2 NR 5 R 6 ; nitro; —NR 5 C(O)R 4 ; —NR 5 S(O) 2 R 4 ; —NR 5 C(O) NR 6 R 7 ; NR 6 R 7 ; cyano; —CO 2 R 5 ; —C(O)NR 6 R 7 ; and —C(O)R 4 ;

wherein said (C 1-20 )alkyl, (C 2-20 )alkenyl, (C 2-20 )alkynyl, (C 3-8 )cycloalkyl(C 1-20 )alkyl; (C 6-12 )aryl(C 1-20 )alkyl, heterocyclyl(C 1-20 )alkyl; and heteroaryl(C 1-20 )alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, each heteroatom is independently a C, Si, chalcogenide, or a pnictide;

or wherein R 6 and R 7 together with the atom to which they are attached form a 5-, 6-, or 7-membered heterocyclyl.

5. The composition of claim 1 , wherein each chalcogenide is independently O, S, or Se.

6. The composition of claim 1 , wherein each pnictide ius independently N or P.

Assignments (2)

CONFIRMATORY LICENSE Recorded Dec 16, 2020

From: UNIVERSITY OF CALIF-LAWRENC BERKELEY LAB

To: UNITED STATES DEPARTMENT OF ENERGY

Reel/Frame 054665/0991 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2020

From: HELMS, BRETT A.; CHRISTENSEN, PETER R.

To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

Reel/Frame 052693/0151 →

Continuity (3)

Continuation PCTUS2018061681 · Nov 16, 2018

Provisional Application 62587148 · Nov 16, 2017

Related Publication 20200283415A1 · Sep 10, 2020

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