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Australian Journal of Chemistry
  An international journal for chemical science
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Flavin Core as Electron Acceptor Component in a Zinc(ii)-Phthalocyanine-Based Dyad

Andreas Gouloumis A D, G. M. Aminur Rahman B, Julia Abel C, Gema de la Torre A, Purificación Vázquez A, Luis Echegoyen C E, Dirk M. Guldi B E and Tomas Torres A E

A Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain.
B Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
C Department of Chemistry, Clemson University, Clemson, SC 29634, USA.
D Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain.
E Corresponding authors. Email: tomas.torres@uam.es, dirk.guldi@chemie.uni-erlangen.de, luis@clemson.edu


Abstract

A zinc(ii)-phthalocyanine-flavin dyad has been synthesized by Heck-type cross-coupling between a flavin that bears a p-iodophenyl group and a phthalocyanine functionalized with a vinyl moiety. Electrochemical experiments reveal that no significant interaction occurs at the ground state between the two electroactive subunits. However, the occurrence of a photoinduced electron transfer in this donor–acceptor conjugate is observed in transient absorption experiments. Charge-separation (i.e., 4.0 × 1011 s–1) and charge-recombination dynamics in benzonitrile (2.2 × 1010 s–1) reveal a remarkable stabilization of the radical ion pair in this solvent.

Australian Journal of Chemistry 61(4) 256–261    doi:10.1071/CH08006
Submitted: 10 January 2008    Accepted: 6 March 2008    Published: 24 April 2008





   
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