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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