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Photochemical Charge Separation in Closely Positioned Donor–Boron Dipyrrin–Fullerene Triads

Authors

  • Channa A. Wijesinghe,

    1. Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051 (USA), Fax: (+1) 316-978-3431
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  • Dr. Mohamed E. El-Khouly,

    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7370
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  • Navaneetha K. Subbaiyan,

    1. Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051 (USA), Fax: (+1) 316-978-3431
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  • Mustafa Supur,

    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7370
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  • Prof. Melvin E. Zandler,

    1. Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051 (USA), Fax: (+1) 316-978-3431
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  • Dr. Kei Ohkubo,

    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7370
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  • Prof. Shunichi Fukuzumi,

    Corresponding author
    1. Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7370
    2. Department of Bioinspired Science, Ewha Womans University, Seoul 120-750 (Korea)
    • Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-7370
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  • Prof. Francis D'Souza

    Corresponding author
    1. Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051 (USA), Fax: (+1) 316-978-3431
    • Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051 (USA), Fax: (+1) 316-978-3431
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Abstract

A series of molecular triads, composed of closely positioned boron dipyrrin–fullerene units, covalently linked to either an electron donor (donor1–acceptor1–acceptor2-type triads) or an energy donor (antenna–donor1–acceptor1-type triads) was synthesized and photoinduced energy/electron transfer leading to stabilization of the charge-separated state was demonstrated by using femtosecond and nanosecond transient spectroscopic techniques. The structures of the newly synthesized triads were visualized by DFT calculations, whereas the energies of the excited states were determined from spectral and electrochemical studies. In the case of the antenna–donor1–acceptor1-type triads, excitation of the antenna moiety results in efficient energy transfer to the boron dipyrrin entity. The singlet-excited boron dipyrrin thus generated, undergoes subsequent energy and electron transfer to fullerene to produce a boron dipyrrin radical cation and a fullerene radical anion as charge-separated species. Stabilization of the charge-separated state in these molecular triads was observed to some extent.

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