Polycyclic aromatic compound embodiments and methods of making and using the same
Disclosed herein are polycyclic aromatic compound embodiments and methods of making and using such compounds. In some embodiments, the polycyclic aromatic compounds comprise an indenoindenodi(benzothiophene) skeleton. The polycyclic aromatic compound embodiments can be used in a variety of devices, such as electronic and/or electrooptical devices.
1. A compound having a structure satisfying Formula I or II,
wherein
each of X 1 and X 2 independently are selected from S, or oxidized forms thereof; O; or NR, wherein each R independently is selected from hydrogen, aliphatic, heteroaliphatic, haloaliphatic, haloheteroaliphatic, aromatic, or an organic functional group;
each of R 3 and R 4 independently is selected from aliphatic, aromatic, heteroaliphatic, or an organic functional group;
each of R 1 , R 2 , R 5 , and R 6 independently is selected from hydrogen, aliphatic, aromatic, heteroaliphatic, or an organic functional group; or R 1 and R 2 together, and/or R 5 and R 6 together, provide an aromatic ring.
2. The compound of claim 1 , wherein each of X 1 and X 2 independently are S or SO 2 .
3. The compound of claim 1 , wherein each of X 1 and X 2 are S.
4. The compound of claim 1 , wherein each of R 3 and R 4 independently are aromatic or an organic functional group.
5. The compound of claim 1 , wherein each of R 3 and R 4 independently are aromatic, wherein the aromatic group comprises one or more substituents other than hydrogen.
6. The compound of claim 5 , wherein the one or more substituents other than hydrogen are aliphatic, aromatic, heteroaliphatic, or an organic functional group.
7. The compound of claim 4 , wherein each organic functional group independently is selected from a combination of an aliphatic, heteroaliphatic, aromatic, haloaliphatic, and/or haloheteroaliphatic group; or aldehyde; aroxy; acyl halide; halogen; nitro; cyano; azide; carboxyl (or carboxylate); amide; ketone; carbonate; imine; azo; carbamate; hydroxyl; thiol; sulfonyl (or sulfonate); oxime; ester; thiocyanate; thioketone; thiocarboxylic acid; thioester; dithiocarboxylic acid or ester; phosphonate; phosphate; silyl ether; sulfinyl; thial; or combinations thereof.
8. The compound of claim 1 , wherein each of R 3 and R 4 independently are selected from alkyl; alkynyl; alkenyl; heteroalkyl; heteroalkynyl; heteroalkenyl; phenyl; naphthyl; pyridinyl; or an organic functional group selected from benzyl, amino, halogen, nitro, alkoxy, aroxy, cyano, thiol, thioether, or hydroxyl.
9. The compound of claim 1 , where R 3 and R 4 are 2,4,6-Me 3 C 6 H 2 , 2,4,6-iPr 3 C 6 H 2 , or 4- t -Bu-2,6-Me 2 CH 6 H 2 .
10. The compound of claim 1 , wherein each of R 1 , R 2 , R 5 , and R 6 independently is selected from H, amino, alkyl, alkynyl, alkenyl, heteroalkyl, heteroalkynyl, heteroalkenyl, an organic functional group; or R 1 and R 2 together provide an aryl or heteroaryl ring and/or R 5 and R 6 together provide an aryl or heteroaryl ring.
11. The compound of claim 1 , wherein R 1 and R 2 together provide a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, a pentacenyl group, a phenanthrenyl group, a chrysenyl group, a pyrenyl group, or other aromatic ring system.
12. The compound of claim 1 , wherein R 5 and R 6 together provide a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, a pentacenyl group, a phenanthrenyl group, a chrysenyl group, a pyrenyl group, or other aromatic ring system.
13. The compound of claim 1 , wherein when any one or more of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 are aromatic groups, the aromatic group comprises one or more substituents other than hydrogen.
14. The compound of claim 13 , wherein one or more substituents other than hydrogen are selected from aliphatic groups, heteroaliphatic groups, aromatic groups, or an organic functional group.
15. The compound of claim 1 , wherein the compound has a structure satisfying one or more of Formulas III or IV
wherein n and m independently are an integer ranging from 1 to 5.
16. The compound of claim 1 , wherein the compound has a structure satisfying one or more of Formula IIIA or Formula IVA
wherein
R 7 and R 8 independently are selected from an aliphatic group, a heteroaliphatic group, an aromatic group, a haloaliphatic group, or an organic functional group;
p and s independently are an integer ranging from 1 to 12
n and m independently are an integer ranging from 1 to 5.
17. The compound of claim 16 , wherein each organic functional group independently is selected from a combination of an aliphatic, heteroaliphatic, aromatic, haloaliphatic, and/or haloheteroaliphatic group; or aldehyde; aroxy; acyl halide; halogen; nitro; cyano; azide; carboxyl (or carboxylate); amide; ketone; carbonate; imine; azo; carbamate; hydroxyl; thiol; sulfonyl (or sulfonate); oxime; ester; thiocyanate; thioketone; thiocarboxylic acid; thioester; dithiocarboxylic acid or ester; phosphonate; phosphate; silyl ether; sulfinyl; thial; or combinations thereof.
18. The compound of claim 1 , wherein the compound is selected from
19. An apparatus, comprising an electronic or electrooptical device selected from an organic light-emitting diode (OLED), an organic field-effect transistor (OFET), or an organic photovoltaic cell (OPV) and further comprising a compound of claim 1 .
20. A thin film, comprising a compound according to claim 1 .