861013-84-5

Upstream product

• 76727-11-2 6,13-diphenyl-pentacene 
• 123-91-1 1,4-dioxane 
• 1333867-44-9 6,13-diiodo-5,14-dihydropentacene 
• 28557-00-8 phenylzinc chloride 
• 1234434-11-7 6,13-bis-trimethylsilanyl-5,14-dihydro-pentacene 

Downstream Products

• 861013-76-5 6,13-diphenyl-5,7,12,14-tetrahydro-pentacene 
• 76727-11-2 6,13-diphenyl-pentacene 

Relevant academic research and scientific papers

Application of zirconacyclopentadienes (metalla-heterocycles) and cross-coupling for the convenient preparative method of 6,13-disubstituted pentacene

Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14- dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and γ-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.

6,13-DIHALOGEN-5,14-DIHYDROPENTACENE DERIVATIVE AND METHOD FOR PRODUCING 6,13-SUBSTITUTED-5,14-DIHYDROPENTACENE DERIVATIVE USING SAME

The present invention provides a 6,13-dihalogen-5,14-dihydropentacene derivative and a method for production thereof. Compounds (b) and (c) are reacted through cross-coupling reaction in the presence of a metal compound and a lithiating agent to synthesize compound (d), which is then halogenated to thereby obtain a 6,13-dihalogen-5,14-dihydropentacene derivative (compound (e)). [wherein X1 and X2 are each a halogen atom, and R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each a hydrogen atom, an optionally substituted C1-C20 hydrocarbon group, etc.]