Issue 8, 2009
From the journal:

Journal of Materials Chemistry

Dendritic oligothiophene-perylene bisimide hybrids: synthesis, optical and electrochemical properties†

Markus K. R. Fischer,a   Theo E. Kaiser,b   Frank Würthner*b  and  Peter Bäuerle*a  

* Corresponding authors

a Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, Ulm, Germany
E-mail: peter.baeuerle@uni-ulm.de
Fax: (+49) 731-502-2840

b Institute of Organic Chemistry, University of Würzburg, Am Hubland, Würzburg, Germany
E-mail: wuerthner@chemie.uni-wuerzburg.de
Fax: (+49) 931-888-4756

Abstract

Novel dendritic oligothiophene-perylene bisimide hybrid (DOTPBI) systems were investigated. Perylene bisimide (PBI) derivatives with phenoxy spacers bearing dendritic oligothiophenes (DOT) up to the third generation (G3) in the bay position, with an increasing number of conjugated thiophene units have been synthesized and characterized as novel functional materials. Investigation of the optoelectronic properties revealed that the perylene core and dendritic oligothiophene units are electronically decoupled. In the DOTPBIs intramolecular fluorescence resonance energy transfer (FRET) and photoinduced electron transfer (PET) from the DOT to the PBI moiety have been investigated by various optical measurements, revealing that the PET process is facilitated with increasing DOT generation and donor strength. Electropolymerization led to interesting cross-linked donor acceptor-type conducting polymer films.

Graphical abstract: Dendritic oligothiophene-perylene bisimide hybrids: synthesis, optical and electrochemical properties

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Article information

DOI
https://doi.org/10.1039/B817158K
Article type
Paper
Submitted
30 Sep 2008
Accepted
20 Nov 2008
First published
16 Jan 2009

J. Mater. Chem., 2009,19, 1129-1141

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Dendritic oligothiophene-perylene bisimide hybrids: synthesis, optical and electrochemical properties

M. K. R. Fischer, T. E. Kaiser, F. Würthner and P. Bäuerle, J. Mater. Chem., 2009, 19, 1129 DOI: 10.1039/B817158K

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