Gendron, David, and Vamvounis, George (2015) Synthesis and reactions of halo-substituted alkylthiophenes : a review. Organic Preparations and Procedures International, 47 (6). pp. 385-414.

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Abstract

[Extract] Introduction: Thiophene chemistry is a flourishing area of organic semiconductors as they are useful for field effect transistors, solar cells and light-emitting diodes.1 This interest stems from the unique optical and electronic properties of thiophene oligomers and polymers coupled with the ease of synthesis and their unique reaction selectivity. Therefore, the preparation of thiophenes is pivotal in this burgeoning area of science. Although there have been several reviews that have focused on the preparation of poly(alkylthiophene)s, this is not the case for oligomeric and monomeric materials. Halo-substituted alkylthiophenes are very useful compounds that react under various conditions to give a plethora of derivatives, which can then be used in the field of materials chemistry.

This review summarizes recent advances (from 1986-2013) in the synthesis and reactivity of these systems to provide a stepping-stone for the design and preparation of more complex thiophene-based molecular architectures for the next generation of materials in photonics and electronics. We will focus first on the preparation of halo-substituted alkylthiophenes by electrophilic aromatic substitution and then their reactivity using various metal-catalyzed cross-coupling methods.

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