Issue 11, 2008

Synthesis and properties of a tetrathiafulvalene–perylene tetracarboxylic diimide–tetrathiafulvalene dyad

Abstract

A donor–acceptor–donor dyad 4 involving 2-sulfur-3-methylthio-6,7-bis(hexylthio)tetrathiafulvalene (TTF) as a donor attached directly to N,N′-dibutylperylene-3,4,9,10-tetracarboxylic diimide (PDI) as an acceptor was synthesized by condensation of N,N′-dibutyl-1,6-dibromo-3,4,9,10-perylenetetracarboxylic diimide and 2-(2-cyanoethylthio-3-methylthio-6,7-bis(hexylthio)tetrathiafulvalene. The cyclic voltammetric (CV) data implied significant intramolecular interaction and the absorption spectrum indicated that there was an intramolecular charge transfer (ICT) interaction between TTF and PDI moieties in dyad 4. Comparing with PDI 13, the fluorescence emission intensity of dyad 4 was quenched almost quantitatively, which might result from the photo-induced electron transfer (PET) interaction between the PDI and TTF moieties in dyad 4. The fluorescence intensity of dyad 4 could be reversibly modulated by sequential oxidation and reduction of the TTF unit using chemical methods. Thus dyad 4 can be regarded as a new reversible fluorescence-redox dependent molecular switch.

Graphical abstract: Synthesis and properties of a tetrathiafulvalene–perylene tetracarboxylic diimide–tetrathiafulvalene dyad

Article information

Article type
Paper
Submitted
03 Jan 2008
Accepted
18 Apr 2008
First published
04 Jun 2008

New J. Chem., 2008,32, 1968-1973

Synthesis and properties of a tetrathiafulvalene–perylene tetracarboxylic diimide–tetrathiafulvalene dyad

Y. Zhang, L. Cai, C. Wang, G. Lai and Y. Shen, New J. Chem., 2008, 32, 1968 DOI: 10.1039/B719844B

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