US2003097010A1PendingUtilityA1

Process for preparing pentacene derivatives

Priority: Sep 27, 2001Filed: Sep 27, 2001Published: May 22, 2003

Est. expirySep 27, 2021(expired)· nominal 20-yr term from priority

C07C 63/72C07C 65/36C07C 15/20C07C 25/22C07C 49/753C07C 65/40C07C 45/46C07C 65/34C07C 2603/52C07C 50/22C07D 337/14C07C 17/35C07C 49/665C07C 1/2078C07C 63/331C07C 49/697C07C 50/24C07C 2527/03C07C 49/675C07D 337/12C07C 51/377C07D 219/06C07C 45/45H10K 71/12H10K 85/623H10K 85/657

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Claims

Abstract

A process for preparing substituted pentacene compounds comprises the step of cyclizing substituted bis(benzyl)phthalic acids using an acid composition comprising trifluoromethanesulfonic acid, the substituted bis(benzyl)phthalic acids being represented by the following general formulas: wherein each R (that is, each of the groups R 1 through R 8 ) is independently an electron-donating group, a halogen atom, a hydrogen atom, or a combination thereof.

Claims

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We claim:

1 . A process for preparing pentacene derivatives comprising the step of cyclizing at least one substituted bis(benzyl)phthalic acid to form the corresponding substituted pentacenedione by using an acid composition comprising trifluoromethanesulfonic acid, said substituted bis(benzyl)phthalic acid being selected from those represented by the following general formulas:

wherein each R group is independently selected from the group consisting of electron-donating groups, halogen atoms, hydrogen atoms, and combinations thereof.

2 . The process of claim 1 wherein each said R group is independently selected from the group consisting of alkyl groups, alkoxy groups, thioalkoxy groups, halogen atoms, hydrogen atoms, and combinations thereof.

3 . The process of claim 2 wherein each said R group is independently selected from the group consisting of alkyl groups, alkoxy groups, hydrogen atoms, and combinations thereof.

4 . The process of claim 3 wherein each said R group is independently selected from the group consisting of alkyl groups and hydrogen atoms.

5 . The process of claim 4 wherein each said R group is independently selected from the group consisting of methyl, n-hexyl, n-nonyl, n-dodecyl, sec-butyl, 3,5,5-trimethylhexyl, 2-ethylhexyl, and hydrogen.

6 . The process of claim 1 wherein said R 2 and said R 6 of said Formula 1(a) are independently selected from the group consisting of electron-donating groups, halogen atoms, and combinations thereof; and said R 1 , R 3 , R 4 , R 5 , R 7 , and R 8 are hydrogen atoms.

7 . The process of claim 1 wherein said R 2 and said R 7 of said Formula 1(b) are independently selected from the group consisting of electron-donating groups, halogen atoms, and combinations thereof; and said R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are hydrogen atoms.

8 . The process of claim 6 wherein said electron-donating group is selected from the group consisting of alkyl groups, alkoxy groups, and thioalkoxy groups.

9 . The process of claim 7 wherein said electron-donating group is selected from the group consisting of alkyl groups, alkoxy groups, and thioalkoxy groups.

10 . The process of claim 8 wherein said R 2 and said R 6 are independently selected from the group consisting of alkyl groups, alkoxy groups, and combinations thereof.

11 . The process of claim 9 wherein said R 2 and said R 7 are independently selected from the group consisting of alkyl groups, alkoxy groups, and combinations thereof.

12 . The process of claim 10 wherein said R 2 and said R 6 are independently alkyl.

13 . The process of claim 11 wherein said R 2 and said R 7 are independently alkyl.

14 . The process of claim 12 wherein said R 2 and said R 6 are independently selected from the group consisting of methyl, n-hexyl, n-nonyl, n-dodecyl, sec-butyl, 3,5,5-trimethylhexyl, 2-ethylhexyl, and hydrogen.

15 . The process of claim 13 wherein said R 2 and said R 7 are independently selected from the group consisting of methyl, n-hexyl, n-nonyl, n-dodecyl, sec-butyl, 3,5,5-trimethylhexyl, 2-ethylhexyl, and hydrogen.

16 . The process of claim 1 further comprising the step of reducing said substituted pentacenedione to the corresponding substituted pentacenediol.

17 . The process of claim 16 further comprising the step of dehydrating said substituted pentacenediol to the corresponding substituted pentacene.

18 . The process of claim 1 further comprising the step of preparing said substituted bis(benzyl)phthalic acid by (a) reacting (1) at least one substituted benzene selected from those represented by the following general formulas:

wherein each of the groups R 1 through R 8 is defined as in claim 1; with (2) pyromellitic dianhydride (or a derivative of pyromellitic dianhydride) to form a substituted bis(benzoyl)phthalic acid; and (b) reducing said substituted bis(benzoyl)phthalic acid to the corresponding substituted bis(benzyl)phthalic acid.

19 . The process of claim 17 further comprising the step of preparing said substituted bis(benzyl)phthalic acid by (a) reacting (1) at least one substituted benzene selected from those represented by the following general formulas:

20 . A process for preparing pentacene derivatives comprising the steps of (a) reacting (1) at least one substituted benzene selected from those represented by the following general formulas:

wherein each of the groups R 1 through R 8 is independently selected from the group consisting of alkyl groups and hydrogen atoms; with (2) pyromellitic dianhydride (or a derivative of pyromellitic dianhydride) to form a substituted bis(benzoyl)phthalic acid; (b) reducing said substituted bis(benzoyl)phthalic acid to the corresponding substituted bis(benzyl)phthalic acid; (c) cyclizing said substituted bis(benzyl)phthalic acid to form the corresponding substituted pentacenedione by using an acid composition comprising trifluoromethanesulfonic acid; (d) reducing said substituted pentacenedione to the corresponding substituted pentacenediol; and (e) dehydrating said substituted pentacenediol to the corresponding substituted pentacene.

21 . A process for preparing a diaryl cyclic ketone comprising the step of cyclizing a diaryl carboxylic acid comprising at least two aromatic rings, one said ring having at least one aromatic ring carbon atom that is directly bonded to a carboxylic acid moiety, and another said ring having at least one aromatic ring carbon atom that is capable of undergoing aromatic electrophilic substitution with said carboxylic acid moiety; said cyclizing being effected by using an acid composition comprising trifluoromethanesulfonic acid.

22 . The process of claim 21 wherein said diaryl carboxylic acid is 2,5-dibenzylterephthalic acid or 4,6-dibenzylisophthalic acid.

23 . The process of claim 21 wherein said diaryl carboxylic acid is substituted.

24 . Substituted pentacenedione compounds represented by the following general formulas:

wherein each R group is independently selected from the group consisting of electron-donating groups, halogen atoms, hydrogen atoms, and combinations thereof.

25 . The compounds of claim 24 wherein each said R group is independently selected from the group consisting of alkyl groups and hydrogen atoms.

26 . Substituted bis(benzyl)phthalic acid compounds represented by the following general formulas:

wherein each R group is independently selected from the group consisting of electron-donating groups, halogen atoms, hydrogen atoms, and monovalent combinations thereof.

27 . The compounds of claim 25 wherein each said R group is independently selected from the group consisting of alkyl groups and hydrogen atoms.

28 . Substituted bis(benzoyl)phthalic acid compounds represented by the following general formulas:

wherein each R group is independently selected from the group consisting of hydrogen atoms and alkyl groups having at least two carbon atoms.

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