Granted Patent B2

US 8,334,391 · App. 11/399,226 · Granted Dec 18, 2012

Abstract

Claims (25)

1. A functionalized heteroacene of the formula/structure

wherein R represents alkyl, alkoxy, aryl, or heteroaryl; each R 1 and R 2 is independently hydrogen (H), alkyl, substituted alkyl, aryl, substituted aryl alkylaryl, a heteroatom containing group, or a halogen; R 3 and R 4 are independently alkyl, substituted alkyl, aryl, substituted aryl, or alkylaryl, a heteroatom containing group, or a halogen; x and y are each independently from 0 to about 12; Z represents sulfur, oxygen, selenium, or NR′ wherein R′ is hydrogen, alkyl, or aryl; and m and n are each independently from 0 to about 3.

2. A functionalized heteroacene of the following formulas/structures

wherein R 5 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, or octadecyl, trifluoromethyl, fluoroethyl, perfluoropropyl, perfluorobutyl, perfluoropentyl, perfluorohexyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, perfluorodecyl, perfluoroundecyl, or perfluorododecyl; phenyl, methylphenyl (tolyl), ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, tridecylphenyl, tetradecylphenyl, pentadecylphenyl, hexadecylphenyl, heptadecylphenyl, octadecylphenyl, trifluoromethylphenyl, fluoroethylphenyl, perfluoropropylphenyl, perfluorobutylphenyl, perfluoropentylphenyl, perfluorohexylphenyl, perfluoroheptylphenyl, perfluorooctylphenyl, perfluorononylphenyl, perfluorodecylphenyl, perfluoroundecylphenyl, or perfluorododecylphenyl; and wherein X is F, CI, Br, CN, or NO 2 .

3. A functionalized heteroacene in accordance with claim 1 of the following formulas

wherein R 5 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, or octadecyl, trifluoromethyl, fluoroethyl, perfluoropropyl, perfluorobutyl, perfluoropentyl, perfluorohexyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, perfluorodecyl, perfluoroundecyl, or perfluorododecyl; phenyl, methylphenyl (tolyl), ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, tridecylphenyl, tetradecylphenyl, pentadecylphenyl, hexadecylphenyl, heptadecylphenyl, octadecylphenyl, trifluoromethylphenyl, fluoroethylphenyl, perfluoropropylphenyl, perfluorobutylphenyl, perfluoropentylphenyl, perfluorohexylphenyl, perfluoroheptylphenyl, perfluorooctylphenyl, perfluorononylphenyl, perfluorodecylphenyl, perfluoroundecylphenyl, or perfluorododecylphenyl; and wherein X is F, CI, Br, CN, or NO 2 .

4. A functionalized heteroacene in accordance with claim 1 wherein R is a heteroaryl with from about 7 to about 37 carbon atoms.

5. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 and R 2 is hydrogen.

6. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 and R 2 is alkyl.

7. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 and R 2 is aryl.

8. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 and R 2 is halogen.

9. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 and R 2 is cyano or nitro.

10. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 3 and R 4 is alkyl.

11. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 3 and R 4 is aryl.

12. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 , R 2 , R 3 , and R 4 is dialkylamine, diarylamine, alkoxy, trialkylsilyl or triarylsilyl.

13. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 , R 2 , R 3 , and R 4 is thienyl, pyridyl, trialkylsilyl, triarylsilyl, or alkoxyalkoxyaryl.

14. A functionalized heteroacene in accordance with claim 1 wherein at least one of R 1 , R 2 , R 3 , R 4 and R 5 is alkyl.

15. A functionalized heteroacene in accordance with claim 1 wherein m is 2.

16. A functionalized heteroacene in accordance with claim 1 wherein m is 1.

17. A functionalized heteroacene in accordance with claim 1 wherein y is a number of from 0 to about 4, a number of from 0 to about 2, or zero.

18. A functionalized heteroacene in accordance with claim 1 wherein alkyl is ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, or eicosanyl.

19. A functionalized heteroacene in accordance with claim 1 wherein aryl is phenyl, tolyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, tridecylphenyl, tetradecylphenyl, pentadecylphenyl, hexadecylphenyl, heptadecylphenyl, octadecylphenyl, naphthyl, methylnaphthyl, ethylnaphthyl, propylnaphthyl, butylnaphthyl, pentylnaphthyl, hexylnaphthyl, heptylnaphthyl, octylnaphthyl, nonylnaphthyl, decylnaphthyl, undecylnaphthyl, dodecyl naphthyl, anthryl, methylanthryl, ethylanthryl, propylanthryl, butylanthyl, pentylanthryl, octylanthryl, nonylanthryl, decylanthryl, undecylanthryl, or dodecylunthryl.

20. A functionalized heteroacene in accordance with claim 1 wherein heteroaryl is thienyl, methylthienyl, ethylthienyl, propylthienyl, butylthienyl, hexylthienyl, heptylthienyl, octylthienyl, nonylthienyl, decylthienyl, undecylthienyl, dodecylthienyl, bithiophenyl, methylbithiophenyl, ethylbithiophenyl, propylbithiophenyl, propylbithiophenyl, butylbithiophenyl, pentylbithiophenyl, hexylbithiophenyl, heptylbithiophenyl, octylbithiophenyl, nonylbithiophenyl, decylbithiophenyl, undecylbithiophenyl, dodecylbithiophenyl, pyridyl, methylpyridyl, ethylpyridyl, propylpyridyl, butylpyridyl, pentylpyridyl, hexylpyridyl, heptylpyridyl, octylpyridyl, nonylpyridyl, decylpyridyl, undecylpyridyl, dodecylpyridyl, thiazolyl, methylthiazolyl, ethylthiazolyl, propylthiazolyl, butylthiazolyl, pentylthiazolyl, hexylthiazolyl, heptylthiazolyl, octylthiazolyl, nonylthiazolyl, decylthiazolyl, undecylthiazolyl, or dodecylthiazolyl.

21. A functionalized heteroacene of the formula/structure

wherein R is alkyl, substituted alkyl, aryl, substituted aryl, or alkylaryl; R 1 , R 2 , R 3 and R 4 are alkyl, substituted alkyl, aryl, substituted aryl, or alkylaryl; x and y are each independently from 0 to about 12; Z is sulfur, oxygen or NR′ wherein R′ is alkyl or aryl; and m and n are each independently from 0 to about 3.

Assignments (9)