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Photophysical properties of non-homoconjugated 1,2-dihydro, 1,2,3,4-tetrahydro and 1,2,3,4,5,6-hexahydro-C60 derivatives

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Abstract

The photophysical properties of a novel series of non-homoconjugated 1,2-di-, 1,2,3,4-tetra-, and 1,2,3,4,5,6-hexasubstituted fullerenes (compounds 1, 2, and 3, respectively) have been systematically investigated. In this report, we examine the effect of substitution pattern of non-homoconjugated derivatized fullerenes on the ground state UV-Vis absorption, triplet state properties (lifetime, quantum yield, extinction coefficient), and singlet oxygen quantum yield. The non-homoconjugated fullerene derivatives 1-3 exhibit higher singlet oxygen quantum yield than analogous homoconjugated Bingel adducts with the same number of saturated C=C bonds and exhibit decreasing quantum yield of singlet oxygen generation upon increasing the degree of functionalization on a single six member ring on the fullerene cage. This trend is similar for triplet quantum yield and triplet lifetime. The triplet extinction coefficient increases with functionalization. A detailed discussion comparing 1, 2, and 3 with functionalized homoconjugated systems and with other non-homoconjugated derivatives is presented.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of California, Los Angeles, CA, 90095-1569, USA

    Khin K. Chin, Shih-Ching Chuang, Luis M. Campos, Christopher S. Foote & Miguel A. Garcia-Garibay

  2. Department of Chemistry and Biochemistry, California State University, Los Angeles, CA, 90032, USA

    Billy Hernandez & Matthias Selke

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  1. Khin K. Chin
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  2. Shih-Ching Chuang
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  3. Billy Hernandez
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  7. Miguel A. Garcia-Garibay
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Correspondence to Miguel A. Garcia-Garibay.

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Chin, K.K., Chuang, SC., Hernandez, B. et al. Photophysical properties of non-homoconjugated 1,2-dihydro, 1,2,3,4-tetrahydro and 1,2,3,4,5,6-hexahydro-C60 derivatives. Photochem Photobiol Sci 7, 49–55 (2008). https://doi.org/10.1039/b714076b

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