Synthesis and characterization of optical and redox properties of bithiophene-functionalized diketopyrrolopyrrole chromophores

Hannah Bürckstümmer, Annike Weissenstein, David Bialas, Frank Würthner

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Abstract

A series of six new 2,2′-bithiophene-functionalized diketopyrrolopyrrole (DPP) dyes 7a-f bearing different electron-donating and electron-withdrawing substituents at the terminal thiophene units was synthesized by palladium-catalyzed cross-coupling reactions. The to date unknown diiodinated DPP 2 and the corresponding boronic ester derivative 3 could be prepared in high yields, and these are shown to be versatile building blocks for the synthesis of DPP-based molecular materials by Negishi, Stille, and Suzuki coupling. The influence of the peripheral substituents on the optical and electrochemical properties of the present series of DPP dyes 7a-f were investigated by UV/vis and steady-state fluorescence spectroscopy and cyclic voltammetry, revealing an appreciable effect on the electronic nature of these dyes. The diamino-substituted DPP derivative 7e exhibits a strong absorption band reaching in the near-infrared (NIR) region, which is a highly desirable feature for application in organic photovoltaics.

Original languageEnglish (US)
Pages (from-to)2426-2432
Number of pages7
JournalJournal of Organic Chemistry
Volume76
Issue number8
DOIs
StatePublished - Apr 15 2011

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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