IP Library › Granted Patent US 12668562

Granted Patent B2

US 12668562 · App. 18/007,639 · Granted Jun 30, 2026

Molecular tetrahedron nanocage, its preparation, and uses thereof

Inventors: Severin T. Schneebeli (West Lafayette, IN); Jianing Li (West Lafayette, IN); Mona Sharafi (Winooski, VT)

Assignee: Purdue Research Foundation

C07C45/46 C07C241/04 C08K5/25 C08K2201/011

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Quick Facts

Patent No.: US 12668562
App. No.: 18/007,639
Granted: Jun 30, 2026
Kind: B2

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Abstract

The present application is directed to a nanocage of Formula (I): wherein A and R are as described herein. The present application is also directed to a process for preparation of a nanocage of Formula (I). Methods of utilizing the nanocage for detecting an analyte in a fluid and for functionalizing a polymer are also described.

Claims (88)

1 . A nanocage of Formula (I):

wherein

each A is independently selected and has the formula

is the point of attachment of A to R;

each R is independently selected and has the formula

indicates the point of attachment of R to A;

R 1 , R 2 , and R 3 are each independently selected from the group consisting of H, halogen, OH, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, —OC 1-20 alkyl, —OC 2-20 alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl, wherein each C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, —OC 1-20 alkyl, —OC 2-20 alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl can be optionally substituted from 1 to 3 times with a substituent selected from the group consisting of H, halogen, OH, C 1-6 alkyl, aryl, and arylalkyl;

R 4 , R 4′ , and R 4″ are each independently selected from the group consisting of H, halogen, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, OH, —OC 1-20 alkyl, —OC 2-20 alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl, wherein each C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, —OC 1-20 alkyl, —OC 2-20 alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl can be optionally substituted from 1 to 3 times with a substituent selected from the group consisting of H, halogen, OH, C 1-6 alkyl, aryl, and arylalkyl;

R 5 , R 5′ , and R 5″ are each independently selected from the group consisting of H, halogen, OH, O(CH 2 ) n —(OCH 2 CH 2 ) m —OC 1-6 alkyl, aryl, hereroaryl, heterocyclyl, —OC 2-20 alkyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, and —NR 10 R 11 ;

R 6 , R 7 , R 8 , and R 9 are each independently selected at each occurrence from the group consisting of H, halogen, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, OH, —OC 1-20 alkyl, —OC 2-20 alkenyl, —O-perfluorinated C 1-20 alkyl, —OC 2-20 alkynyl, aryl, heteroaryl, heterocyclyl, and —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl, wherein each C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, —OC 1-20 alkyl, —OC 2-20 alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl can be optionally substituted from 1 to 3 times with a substituent selected from the group consisting of H, halogen, OH, C 1-6 alkyl, aryl, and arylalkyl;

R 10 and R 11 are each independently selected from the group consisting of H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroarylalkyl, heterocyclylalkyl, and arylalkyl, wherein each C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, aryl, heteroarylalkyl, heterocyclylalkyl, and arylalkyl can be optionally substituted from 1 to 3 times with a substituent selected from the group consisting of H, C 1-6 alkyl, heteroarylalkyl, heterocyclylalkyl, and arylalkyl;

X 1 and X 2 are absent or are independently selected from the group consisting of C 1-6 alkylene, C 3-8 cycloalkylene, and arylene, wherein C 1-6 alkylene, C 3-8 cycloalkylene, and arylene can be optionally substituted from 1 to 3 times with H or C 1-6 alkyl;

p is 1 to 3;

n is 1 to 10; and

m is 1 to 10.

2 . The nanocage of claim 1 , wherein the nanocage is T d -symmetric.

3 . The nanocage of claim 1 , wherein the nanocage has a height from 15 Å to 40 Å.

4 . The nanocage of claim 1 , wherein the nanocage has a height from 20 Å to 25 Å.

5 . The nanocage of claim 1 , wherein R 1 , R 2 , and R 3 are Me, R 4 is —OMe, R 5 is —O(CH 2 ) 4 —(OCH 2 CH 2 ) 3 —OMe.

6 . A process for preparation of a nanocage of Formula (I):

wherein each A is independently selected and has the formula

is the point of attachment of A to R;

each R is independently selected and has the formula

indicates the point of attachment of R to A;

R 1 , R 2 , and R 3 are each independently selected from the group consisting of H, halogen, OH, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, —OC 1-20 alkyl, —OC 2-20 alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl, wherein each C 1-20 alkyl, C 2-20 alkenyl, alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl can be optionally substituted from 1 to 3 times with a substituent selected from the group consisting of H, halogen, OH, C 1-6 alkyl, aryl, and arylalkyl;

R 5 , R 5′ , and R 5″ are each independently selected from the group consisting of H, halogen, OH, —O(CH 2 ) n —(OCH 2 CH 2 ) m —OC 1-6 alkyl, aryl, hereroaryl, heterocyclyl, —OC 2-20 alkyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, and —NR 10 R 11 ;

p is 1 to 3;

n is 1 to 10; and

m is 1 to 10, said process comprising:

providing one or more compounds of Formula (II) having the structure:

and

forming the nanocage of Formula (I) from the one or more compounds of Formula (II).

7 . The process according to claim 6 , wherein said forming the nanocage of Formula (I) comprises:

reacting the one or more compounds of Formula (II) with one or more compounds of Formula (III):

to produce the nanocage of Formula (I).

8 . The process according to claim 6 further comprising:

providing one or more compounds of Formula (IV) having the structure:

and

forming the one or more compounds of Formula (II) from the one or more compounds of Formula (IV).

9 . The process according to claim 8 further comprising:

providing one or more compounds of Formula (VI) having the structure:

and

forming the one or more compounds of Formula (IV) from the one or more compounds of Formula (VI).

10 . The process according to claim 9 further comprising:

providing one or more compounds of Formula (VII) having the structure:

and

forming the one or more compounds of Formula (VI) from the one or more compounds of Formula (VII).

11 . The process according to claim 10 , wherein said forming the one or more compounds of Formula (VI) comprises:

reacting the compound of Formula (VII) with an oxidizing agent to produce the one or more compounds of Formula (VI).

12 . The process according to claim 6 further comprising:

providing one or more compounds of Formula (VIII) having the structure:

and

forming the one or more compounds of Formula (VII) from the one or more compounds of Formula (VIII).

13 . The process according to claim 12 further comprising:

providing one or more compounds of Formula (X) having the structure:

and

forming the one or more compounds of Formula (VIII) from the one or more compounds of Formula (X).

14 . The process according to claim 13 further comprising:

providing one or more compounds of Formula (XII) having the structure:

and

forming the one or more compounds of Formula (X) from the one or more compounds of Formula (XII).

15 . A method for detecting an analyte in a fluid comprising:

providing a sensor comprising a nanocage of Formula (I):

wherein each A is independently selected and has the formula

is the point of attachment of A to R;

each R is independently selected and has the formula

indicates the point of attachment of R to A;

R 1 , R 2 , and R 3 are each independently selected from the group consisting of H, halogen, OH, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, perfluorinated C 1-20 alkyl, aryl, hereroaryl, heterocyclyl, —OC 1-20 alkyl, —OC 2-20 alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl, wherein each C 1-20 alkyl, C 2-20 alkenyl, alkenyl, —OC 2-20 alkynyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, —COOC 1-20 alkyl, —COO perfluorinated C 1-20 alkyl, —COOaryl, —CONHC 1-20 alkyl, —CONHC 2-20 alkenyl, —CONHC 2-20 alkynyl, —CONH perfluorinated C 1-20 alkyl, —CONH-aryl, —CONH-heteroaryl, and —CONH-heterocyclyl can be optionally substituted from 1 to 3 times with a substituent selected from the group consisting of H, halogen, OH, C 1-6 alkyl, aryl, and arylalkyl;

R 5 , R 5′ , and R 5″ are each independently selected from the group consisting of H, halogen, OH, —O(CH 2 ) n —(OCH 2 CH 2 ) m —OC 1-6 alkyl, aryl, hereroaryl, heterocyclyl, —OC 1-20 alkyl, —O-perfluorinated C 1-20 alkyl, —Oaryl, and —NR 10 R 11 ;

p is 1 to 3;

n is 1 to 10; and

m is 1 to 10;

providing a fluid containing an analyte; and

contacting a fluid containing the analyte with the sensor to capture the analyte in the nanocage and detect the analyte in the fluid.

16 . The method according to claim 15 , wherein the sensor further comprises:

a substrate having a surface with a layer of the nanocage of Formula (I) covering at least 5% of the surface.

17 . The method according to claim 15 further comprising:

providing a signal generator operatively associated with said sensor, said method further comprising:

producing a signal with the signal generator when said analyte is captured by said sensor.

18 . The method according to claim 15 , wherein the analyte is selected from the group consisting of polyvinylpyrrolidone (PVP), poly(isobutylene-alt-n-octyl maleimide) (POI), picrocrocin, curcumin, and components of chinese tea.