Issue 29, 2013
From the journal:

RSC Advances

Thiazolo[5,4-d]thiazoles – promising building blocks in the synthesis of semiconductors for plastic electronics

David Bevk,ab   Lidia Marin,ab   Laurence Lutsen,b   Dirk Vanderzandeab  and  Wouter Maes*a  

* Corresponding authors

a Design & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Agoralaan 1-Building D, B-3590 Diepenbeek, Belgium
E-mail: wouter.maes@uhasselt.be
Fax: +32 11 268399
Tel: +32 11 268312

b IMEC, IMOMEC, Wetenschapspark 1, B-3590 Diepenbeek, Belgium

Abstract

The thiazolo[5,4-d]thiazole fused (bi)heterocycle is an electron deficient system with high oxidative stability and a rigid planar structure, enabling efficient intermolecular π–π overlap. The parent thiazolo[5,4-d]thiazole moiety hence already possesses some appealing features towards applications in organic electronics. Moreover, aryl-functionalized thiazolo[5,4-d]thiazole derivatives – expanding the conjugated backbone of the semiconducting material – are easily prepared. Surprisingly, interest in thiazolo[5,4-d]thiazole-based materials has been rather low, until quite recently, when the high potential of these molecules was widely recognized, notably in the field of organic photovoltaics. Despite the almost exponential growth of activity, the synthetic chemistry behind these molecules has only been explored to a minor extent and there is plenty of room for improvement and broadening of the material scope. In this review, an overview of the currently available synthetic methods and the range of materials prepared to date, together with their basic material properties and main applications, is provided, with the aim to facilitate and stimulate further progress in thiazolo[5,4-d]thiazole-based materials science.

Graphical abstract: Thiazolo[5,4-d]thiazoles – promising building blocks in the synthesis of semiconductors for plastic electronics

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Article information

DOI
https://doi.org/10.1039/C3RA40851E
Article type
Review Article
Submitted
20 Feb 2013
Accepted
07 Apr 2013
First published
09 Apr 2013

RSC Adv., 2013,3, 11418-11431

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Thiazolo[5,4-d]thiazoles – promising building blocks in the synthesis of semiconductors for plastic electronics

D. Bevk, L. Marin, L. Lutsen, D. Vanderzande and W. Maes, RSC Adv., 2013, 3, 11418 DOI: 10.1039/C3RA40851E

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