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

Andreas Gouloumis; G. M. Aminur Rahman; Julia Abel; Gema de la Torre; Purificación Vázquez; Luis Echegoyen; Dirk M. Guldi; Tomas Torres

doi:10.1071/CH08006

RESEARCH FRONT

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

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 61(4) 256-261 https://doi.org/10.1071/CH08006
Submitted: 10 January 2008 Accepted: 6 March 2008 Published: 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.

Acknowledgements

The authors are grateful to the financial support of MEC (CTQ2005–08933/BQU), Comunidad de Madrid (S-0505/PPQ/000225), ESF-MEC (Sohyd project), SFB 583, DFG (GU 517/4–1), FCI, and the Office of Basic Energy Sciences of the USA Department of Energy, and the National Science Foundation AJA and LE (Grant number CHE-0509989).

References

^* ZnPc (reference Pc, Zinc^II 2,9,16,23-tetra-tert-butylphthalocyanine) is commercially available and has an absorption spectrum in THF, which resembles that of vinylphthalocyanine 5.

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

Abstract

Acknowledgements

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