Diphenic acid → 9-Oxofluorene-4-carboxylic acid

HRID 10123

Reaction equation

[C:1]1([C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[C:2](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:3]([OH:5])=O>S(=O)(=O)(O)O>[CH:8]1[CH:9]=[C:1]2[C:10]3[C:11]([C:12]([OH:14])=[O:13])=[CH:15][CH:16]=[CH:17][C:18]=3[C:3](=[O:5])[C:2]2=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The following steps are suitable for synthesizing some charge transport materials of this invention involving a linking reaction as described in the following. In the first step, diphenic acid or its derivative is dissolved in large access of concentrated sulfuric acid and the solution is heated at approximately 70° C. for about 10 minutes. The product, 9-fluorenone-4-carboxylic acid or its derivative, is isolated. In the second step, 9-fluorenone-4-carboxylic acid or its derivative is chlorinated with thionyl chloride to form 9-fluorenone-4-carbonyl chloride or its derivative. Then, 9-fluorenone-4-carbonyl chloride or its derivative reacts with a diol, a dithiol, a diamine, a hydroxylamine, a hydroxythiol, or a thioamine in the presence of triethylamine. Non-limiting examples of suitable dithiol are 4,4′-thiobisbenzenethiol, 1,4-benzenedithiol, 1,3-benzenedithiol, sulfonyl-bis(benzenethiol), 2,5-dimecapto-1,3,4-thiadiazole, 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 1,5-pentanedithiol, and 1,6-hexanedithiol. Non-limiting examples of suitable diols are 2,2′-bi-7-naphtol, 1,4-dihydroxybenzene, 1,3-dihydroxybenzene, 10,10-bis(4-hydroxyphenyl)anthrone, 4,4′-sulfonyldiphenol, bisphenol, 4,4′-(9-fluorenylidene)diphenol, 1,10-decanediol, 1,5-pentanediol, diethylene glycol, 4.4′-(9-fluorenylidene)-bis(2-phenoxyethanol), bis(2-hydroxyethyl) terephthalate, bis[4-(2-hydroxyethoxy)phenyl] sulfone, hydroquinone-bis (2-hydroxyethyl)ether, and bis(2-hydroxyethyl) piperazine. Non-limiting examples of suitable diamine are diaminoarenes, and diaminoalkanes. Non-limiting examples of suitable hydroxylamine are p-aminophenol and fluoresceinamine. Non-limiting examples of suitable hydroxythiol are monothiohydroquinone and 4-mercapto-1-butanol. Non-limiting example of suitable thioamine is p-aminobenzenethiol. The intermediate product is isolated and dried. Then, the intermediate product is reacted with malononitrile in the presence of piperidine to form the dimeric electron transport material, which can be purified and dried.

Workup

customThe following steps are suitable for synthesizing some charge transport materials of this invention
customa linking reaction

Sources & evidence

ORD record: ord-bbc38cb4d21e4dbba0e6138c6543b664
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094510B2

Linked notes

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