Synthetic Routes toward Asymmetrically Substituted (Functionalized) 
4H-Cyclopenta[2,1-b:3,4-b′]dithiophenes

Wouter Vanormelingen; Pieter Verstappen; Veronique Maes; David Bevk; Laurence Lutsen; Dirk Vanderzande; Wouter Maes

doi:10.1055/s-0033-1339707

Synlett, Table of Contents

Synlett 2013; 24(18): 2389-2392
DOI: 10.1055/s-0033-1339707

letter

Synthetic Routes toward Asymmetrically Substituted (Functionalized) 4H-Cyclopenta[2,1-b:3,4-b′]dithiophenes

Authors

Wouter Vanormelingen

^aImec-Imomec, Wetenschapspark 1, 3590 Diepenbeek, Belgium

^bDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO), Hasselt University, Agoralaan 1, Building D, 3590 Diepenbeek, Belgium Fax: +32(11)268299 Email: wouter.maes@uhasselt.be
Pieter Verstappen

^aImec-Imomec, Wetenschapspark 1, 3590 Diepenbeek, Belgium

^bDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO), Hasselt University, Agoralaan 1, Building D, 3590 Diepenbeek, Belgium Fax: +32(11)268299 Email: wouter.maes@uhasselt.be
Veronique Maes

^aImec-Imomec, Wetenschapspark 1, 3590 Diepenbeek, Belgium

^bDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO), Hasselt University, Agoralaan 1, Building D, 3590 Diepenbeek, Belgium Fax: +32(11)268299 Email: wouter.maes@uhasselt.be
David Bevk

^aImec-Imomec, Wetenschapspark 1, 3590 Diepenbeek, Belgium

^bDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO), Hasselt University, Agoralaan 1, Building D, 3590 Diepenbeek, Belgium Fax: +32(11)268299 Email: wouter.maes@uhasselt.be
Laurence Lutsen

^aImec-Imomec, Wetenschapspark 1, 3590 Diepenbeek, Belgium
Dirk Vanderzande

^aImec-Imomec, Wetenschapspark 1, 3590 Diepenbeek, Belgium

^bDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO), Hasselt University, Agoralaan 1, Building D, 3590 Diepenbeek, Belgium Fax: +32(11)268299 Email: wouter.maes@uhasselt.be
Wouter Maes*

^aImec-Imomec, Wetenschapspark 1, 3590 Diepenbeek, Belgium

^bDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO), Hasselt University, Agoralaan 1, Building D, 3590 Diepenbeek, Belgium Fax: +32(11)268299 Email: wouter.maes@uhasselt.be

Abstract

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Abstract

A two-step synthetic protocol involving (i) a Wittig-type carbonyl olefination, and (ii) regioselective alkylation of the exocyclic double bond with LiAlH₄ and an alkyl bromide, was developed as an alternative to the recently reported three-step synthetic approach toward asymmetrically substituted/functionalized 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes. The two routes are rather complementary, with specific advantages depending on the desired substitution pattern, and are of particular appeal for the construction of semiconducting materials to be applied in organic photovoltaics.

Key words

cyclopentadithiophene - Friedel–Crafts cyclization - Wittig reaction - reduction - organic photovoltaics

Full Text

References

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Supplementary Material

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