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

Patent metadata

Field	Value
Publication number	US-10934290-B2
Application number	US-201615187644-A
Country	US
Kind code	B2
Filing date	Jun 20, 2016
Priority date	Jun 22, 2015
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

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 each D ring independently is selected from phenyl, pyridinyl, benzo[1,2-b:4,5-b′]dithiophenyl; benzo[1,2-b:4,5-b′]difuranyl; or 1,5-dihydropyrrolo[2,3-f]indolyl; and each D ring is connected to other rings of the compound in a para-substitution pattern;
each A ring independently is phenyl, pyridinyl, pyridinyl comprising an aliphatic-substituted nitrogen atom, benzo[c][1,2,5]thiadiazolyl, benzo[c][1,2,5]oxadiazolyl, or 2H-benzo[d][1,2,3]triazolyl; and each A ring is connected to other rings of the compound in a para-substitution pattern;
each “EDG” independently is selected from alkoxy, thioether, amide, amine, hydroxyl, thiol, acyloxy, aliphatic, or aryl;
each “EAG” independently is selected from sulfonate; pyridinyl; alkyl halide; cyano; quaternary amine; nitro; aldehyde; ketone; carboxylic acid; —C(O)R b , wherein R b is selected from alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroalkenyl, heteroalkynyl, or heteroaryl; or acyl halide;
each q independently is an integer selected from 0, 1, or 2;
each r independently is an integer selected from 0, 1, or 2;
n is an integer selected from 0 to 18;
m is an integer selected from 0 to 18;
p is an integer selected from 1 to 10; provided that the compound comprises a total number of rings ranging from 6 to 20; and
wherein the compound is not, or is other than,

wherein the compound is not, or is other than, a non-functionalized nanohoop consisting of phenyl rings; and
wherein the compound is not, or is other than, a compound consisting of phenyl and pyridinyl rings, wherein any pyridinyl ring lacks N-substitution with an aliphatic group.

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

3. The compound of claim 1 , wherein each EAG independently is selected from cyano, alkyl halide, pyridinyl, or combinations thereof.

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

wherein
one of a, b, c, or d is carbon, nitrogen, or nitrogen comprising an aliphatic group and each other a, b, c, or d is carbon;
each n′ independently is an integer selected from 1 to 18.

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

wherein (i) one of a, b, c, or d is carbon and further wherein the A ring comprises one or more electron-accepting groups selected from sulfonate; pyridinyl; alkyl halide; cyano; quaternary amine; nitro; aldehyde; ketone; carboxylic acid; —C(O)R b , wherein R b is selected from akyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroalkenyl, heteroalkynyl, or heteroaryl; or acyl halide; and each other a, b, c, or d is carbon; or (ii) one of a, b, c, or d is nitrogen comprising an aliphatic group and each other a, b, c, or d is carbon.

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

wherein the A phenyl ring comprises one or more electron-accepting groups selected from sulfonate;
pyridinyl; alkyl halide; cyano; quaternary amine; nitro; aldehyde; ketone; carboxylic acid; —C(O)R b, wherein R b is selected from alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroalkenyl, heteroalkynyl, or heteroaryl; or acyl halide; and the D phenyl ring comprises one or two EDGs.

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

wherein R 1 is selected from alkyl, alkenyl, alkynyl, aryl, heteroalkyl, heteroalkenyl, heteroalkynyl, heteroaryl, or hydrogen.

8. 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.

9. 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.

10. 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.

11. 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.

12. 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.

13. A method of making a compound of claim 1 , comprising exposing a compound of a formula

to a reducing agent to thereby produce the compound of claim 1 .

14. The method of claim 13 , wherein the reducing agent is an organic salt.

15. The method of claim 13 , wherein the reducing agent is a metal naphthalenide.

16. The method of claim 13 , wherein the reducing agent is sodium naphthalenide.

17. The compound of claim 1 , wherein each D ring independently is phenyl, pyridinyl, benzo[1,2-b:4,5-b′]dithiophenyl; benzo[1,2-b:4,5-b′]difuranyl; or 1,5-dihydropyrrolo[2,3-f]indolyl; and each A ring independently is a phenyl ring comprising one or two EAGs, or pyridinyl comprising an aliphatic-substituted nitrogen atom.

18. The compound of claim 1 , wherein:
each D ring independently is benzo[1,2-b:4,5-b′]dithiophenyl; benzo[1,2-b:4,5-b′]difuranyl; 1,5-dihydropyrrolo[2,3-f]indolyl; or 4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene; and
each A ring independently is benzo[c][1,2,5]thiadiazolyl, benzo[c][1,2,5]oxadiazolyl, or 2H-benzo[d][1,2,3]triazolyl.

19. The compound of claim 1 , wherein:
each D ring independently is benzo[1,2-b:4,5-b′]dithiophenyl; benzo[1,2-b:4,5-b′]difuranyl; or 1,5-dihydropyrrolo[2,3-f]indolyl; and
each A ring independently is phenyl or pyridinyl comprising an aliphatic-substituted nitrogen atom; or wherein
each D ring independently is selected from phenyl, pyridinyl, benzo[1,2-b:4,5-b′]dithiophenyl; benzo[1,2-b:4,5-b′]difuranyl; or 1,5-dihydropyrrolo[2,3-f]indolyl; and
each A ring independently is benzo[c][1,2,5]thiadiazolyl, benzo[c][1,2,5]oxadiazolyl, or 2H-benzo[d][1,2,3]triazolyl.

20. A compound having a structure satisfying a formula

Assignees

• Univ Oregon

Inventors

• Jasti Ramesh
• Darzi Evan R

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D471/18

  Bridged systems · CPC title

• C07D471/08

  Bridged systems · CPC title

• C07D471/22 Primary

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

• H01L51/0071

  Electricity · mapped topic