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A Versatile and Efficient Synthesis of Bithiophene-Based Dicarboxaldehydes From a Common Synthon

A Versatile and Efficient Synthesis of Bithiophene-Based Dicarboxaldehydes From a Common Synthon

Achala Bhuwalka, Jared F Mike, Jeremy J Intemann, Arkady Ellern, Malika Jeffries-El

Org Biomol Chem. 2015 Sep 28;13(36):9462-70.

PMID: 26248770

Abstract:

Bithiophene dicarboxaldehydes are promising electron-rich building blocks for the development of arylene vinylene-based organic semiconductors, but their use has been limited due to their synthetic inaccessibility. To facilitate the facile synthesis of these compounds we have prepared a novel functional bithiophene, namely 2,2'-(3,3'-dibromo-[2,2'-bithiophene]-5,5'-diyl)bis(5,5-dimethyl-1,3-dioxane) in two high yielding steps from 3,3',5,5'-tetrabromo-2,2'-bithiophene. This synthon is readily transformed into variety of bithiophene-based dicarboxaldehydes, also in high yields. The use of these functional molecules in the synthesis of arylene vinylene-linked donor-acceptor copolymers is demonstrated by the synthesis of two copolymers with electron deficient benzobisazoles.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP51751441	3,3'-Dibromo-2,2'-bithiophene		51751-44-1	Price

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