Flavin Core as Electron Acceptor Component in a Zinc(II)-Phthalocyanine-Based Dyad

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Contents Vol 61(4)

doi:10.1071/CH08006

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, 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





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

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.