Donor-acceptor nanohoop compounds and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-2016372684-A1
Application number	US-201615187644-A
Country	US
Kind code	A1
Filing date	Jun 20, 2016
Priority date	Jun 22, 2015
Publication date	Dec 22, 2016
Grant date	—

Abstract

Disclosed herein are embodiments of nanostructure compounds that exhibit unique shape configurations, such as nanohoops. The compounds disclosed herein exhibit unique chemical and electrochemical properties that can be tuned and modified to facilitate their use in a variety of different applications.

First claim

We claim:

1 . A compound having a structure satisfying a formula

wherein the compound comprises at least one D ring and at least one A ring; wherein
each D ring independently is an aryl ring comprising an electron-donating group or a heteroaryl ring optionally comprising an electron-donating group;
each A ring independently is an aryl ring comprising an electron-accepting group or a heteroaryl ring comprising an electron-accepting group or one or more heteroatoms and/or substituents that are capable of accepting electron density from a core ring to which they are attached, wherein the core ring is a ring comprising two carbon atoms that each are attached to two different rings of the compound;
each of n and m independently is an integer selected from 0 to 100;
p is an integer selected from 1 to 100; and
wherein the compound is not, or is other than,

2 . The compound of claim 1 , wherein the D ring is selected from phenyl optionally substituted with one or more electron-donating substituents; benzo[1,2-b:4,5-b′]dithiophenyl optionally substituted with one or more electron-donating substituents; benzo[1,2-b:4,5-b′]difuranyl optionally substituted with one or more electron-donating substituents; or 1,5-dihydropyrrolo[2,3-f]indolyl optionally substituted with one or more electron-donating substituents.

3 . The compound of claim 1 , wherein the D ring is 4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene.

4 . The compound of claim 1 , wherein the D ring is phenyl.

5 . The compound of claim 2 , wherein the one or more electron-donating substituents is selected from alkoxy, thioether, amide, amine, hydroxyl, thiol, acyloxy, aliphatic, aryl, or combinations thereof.

6 . The compound of claim 1 , wherein the A ring is selected from phenyl substituted with one or more electron-accepting substituents; pyridinyl substituted with an aliphatic or aryl group; benzo[c][1,2,5]thiadiazolyl; benzo[c][1,2,5]oxadiazolyl; or 2H-benzo[d][1,2,3]triazolyl.

7 . The compound of claim 6 , wherein the electron-accepting substituents is selected from aldehyde, ketone, ester, carboxylic acid, acyl, acyl halide, cyano, sulfonate, nitro, nitroso, quaternary amine, alkyl halide, or combinations thereof.

8 . The compound of claim 1 , wherein the compound has a structure satisfying any one or more of the following formulas:

wherein
each of a, b, c, and d independently is selected from carbon or nitrogen;
each n′ independently is an integer selected from 1 to 100;
each “EDG” group independently is selected from alkoxy, thioether, amide, amine, hydroxyl, thiol, acyloxy, aliphatic, aryl, or combinations thereof;
each “EAG” group independently is selected from aldehyde, ketone, ester, carboxylic acid, acyl, acyl halide, cyano, sulfonate, nitro, nitroso, quaternary amine, pyridinyl, pyridinyl comprising a nitrogen atom functionalized with an aliphatic or aryl group, alkyl halide, or combinations thereof;
each q independently is an integer selected from 0 to 4; and
each r independently is an integer selected from 0 to 4.

9 . The compound of claim 1 , wherein the compound has a structure satisfying a formula

10 . The compound of claim 1 , wherein the compound has a structure satisfying a formula selected from

11 . The compound of claim 1 , wherein the compound is selected from

12 . The compound of claim 1 , wherein the compound is a functionalized nanohoop compound that exhibits a LUMO energy level ranging from greater than −2.0 eV to −5 eV.

13 . The compound of claim 1 , wherein the compound is a functionalized nanohoop compound that exhibits a LUMO energy level ranging from −2.5 eV to −4.0 eV.

14 . The compound of claim 1 , wherein the compound is a functionalized nanohoop compound that exhibits a HOMO energy level ranging from −5.0 eV to −7 eV.

15 . The compound of claim 1 , wherein the compound is a functionalized nanohoop compound that exhibits a HOMO energy level ranging from −5.2 eV to −6.5 eV.

16 . A device, comprising a compound according to claim 1 , wherein the device is an organic photovoltaic device, an organic field effect transistor, a molecular wire, or an organic light emitting diode.

17 . A method of making a compound, comprising exposing a compound having a structure satisfying Formula V to a reducing agent to produce the compound

18 . The method of claim 17 , wherein the reducing agent is an organic salt.

19 . The method of claim 17 , wherein the reducing agent is a metal naphthalenide.

20 . The method of claim 17 , wherein the reducing agent is sodium naphthalenide.

Assignees

• Univ Oregon

Inventors

• Jasti Ramesh
• Darzi Evan R

Classifications

• C07D471/08

  Bridged systems · CPC title

• C07D471/18

  Bridged systems · CPC title

• C07D471/22 Primary

  in which the condensed systems contains four or more hetero rings · CPC title

• H01L51/4253

  Electricity · mapped topic

• H01L51/0072 Primary

  Electricity · mapped topic