Synthesis and Properties of Regioregular Poly(3-substituted thiophene) Bearing Disiloxane Moiety in the Substituent. Remarkably High Solubility in Hexane

Regioregular poly(3-substituted thiophene) derivative bearing pentamethyldisiloxane moiety at the 3-substituent is prepared by nickel-catalyzed polymerization reactions with dehydrobrominative or debrominative generation of the organometallic monomer. The monomer precursors 2-bromo-3-(4-pentamethyld...

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Bibliographic Details
Published in:Chemistry letters 2014-05, Vol.43 (5), p.640-642
Main Authors: Mori, Atsunori, Ide, Kenji, Tamba, Shunsuke, Tsuji, Satoru, Toyomori, Yuka, Yasuda, Takeshi
Format: Article
Language:English
Subjects:
Bearing
Catalysts
Hexanes
Metalorganic compounds
Monomers
Nickel
Polythiophene
Thiophenes
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Summary:Regioregular poly(3-substituted thiophene) derivative bearing pentamethyldisiloxane moiety at the 3-substituent is prepared by nickel-catalyzed polymerization reactions with dehydrobrominative or debrominative generation of the organometallic monomer. The monomer precursors 2-bromo-3-(4-pentamethyldisiloxybutan-1-yl)thiophene (1a) and 2,5-dibromo-3-(4-pentamethyldisiloxybutan-1-yl)thiophene (1b) are prepared from 3-methylthiophene with 4–5 steps in overall good yields. Treatment of 1a with TMPMgCl·LiCl at room temperature for 3 h forms an organometallic monomer and following the addition of a nickel catalyst affords the corresponding polythiophene bearing a disiloxane moiety in the side chain. The reaction of 1b with Grignard reagent leads to the similar monomer and addition of a catalytic amount of [NiCl2(dppe)] also affords polythiophene in highly regioregular manners. The obtained polythiophene is found to be dissolved in a hydrocarbon such as hexane.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.131222