Issue 23, 2005
From the journal:

Journal of Materials Chemistry

Photoinduced electron- and energy-transfer processes of [60]fullerene covalently bonded with one and two zinc porphyrin(s): effects of coordination of pyridine and diazabicyclooctane to Zn atom†

Atula S. D. Sandanayaka,a   Kei-ichiro Ikeshita,b   Yasuyuki Araki,a   Nobuhiro Kihara,b   Yoshio Furusho,b   Toshikazu Takata*c  and  Osamu Ito*a  

* Corresponding authors

a Institute of Multidisciplinary Research for Advanced Materials, CREST (JST), Tohoku University, Katahira 2-1-1, Aoba-ku, Sendai, Japan
E-mail: ito@tagen.tohoku.ac.jp

b Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai-shi, Osaka, Japan

c Department of Organic and Polymeric Materials, Tokyo Institute of Technology, Ookayama, Meguro, Tokyo, Japan

Abstract

C60–zinc porphyrin (ZnP) dyad (ZnP–C60) and triad (ZnP–C60–ZnP) were synthesized to probe energy-transfer and electron-transfer processes in the absence and presence of pyridine and diazabicyclooctane (DABCO). The syntheses of C60–ZnP and ZnP–C60–ZnP were carried out by Diels–Alder cycloaddition between sulfolene moiety-containing porphyrin and C60. The photoinduced electron-transfer processes between the spatially positioned C60 and ZnP in the dyad and triad systems were investigated by time-resolved transient absorption and fluorescence measurements with changing solvent polarity. Upon excitation of the ZnP moiety, charge separation via an excited singlet state of ZnP takes place competitively with energy transfer to C60 generating the excited singlet state of C60, from which charge-separated states (ZnP˙+–C60˙− and ZnP˙+–C60˙−–ZnP) are also generated in polar solvents. Rates and efficiencies of energy transfer and charge separation for the triad are higher than those of the dyad. The generated charge-separated species recombine with lifetimes in the rage of 240–330 ns in polar solvents such as DMF, PhCN, and THF for both dyad and triad. In o-dichlorobenzene, although the lifetimes of charge-separated states are very short (<20 ns), coordination of DABCO and pyridine to ZnP in the dyad and triad producing relatively stable coordinated complexes gives rise to prolongation of the charge-separated states up to 460 ns.

Graphical abstract: Photoinduced electron- and energy-transfer processes of [60]fullerene covalently bonded with one and two zinc porphyrin(s): effects of coordination of pyridine and diazabicyclooctane to Zn atom

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Article information

DOI
https://doi.org/10.1039/B500030K
Article type
Paper
Submitted
04 Jan 2005
Accepted
18 Feb 2005
First published
01 Mar 2005

J. Mater. Chem., 2005,15, 2276-2287

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Photoinduced electron- and energy-transfer processes of [60]fullerene covalently bonded with one and two zinc porphyrin(s): effects of coordination of pyridine and diazabicyclooctane to Zn atom

A. S. D. Sandanayaka, K. Ikeshita, Y. Araki, N. Kihara, Y. Furusho, T. Takata and O. Ito, J. Mater. Chem., 2005, 15, 2276 DOI: 10.1039/B500030K

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