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      Taming C 60 fullerene: tuning intramolecular photoinduced electron transfer process with subphthalocyanines†

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          Abstract

          Two subphthalocyanine–C 60 fullerene electron donor–acceptor conjugates have been prepared from electron deficient subphthalocyanines and C 60, with evidence of an ultrafast oxidative electron transfer from C 60 to the subphthalocyanines.

          Abstract

          Two subphthalocyanine–C 60 conjugates have been prepared by means of the 1,3-dipolar cycloaddition reaction of (perfluoro) or hexa(pentylsulfonyl) electron deficient subphthalocyanines to C 60. Comprehensive assays regarding the electronic features – in the ground and excited state – of the resulting conjugates revealed energy and electron transfer processes upon photoexcitation. Most important is the unambiguous evidence – in terms of time-resolved spectroscopy – of an ultrafast oxidative electron transfer evolving from C 60 to the photoexcited subphthalocyanines. This is, to the best of our knowledge, the first case of an intramolecular oxidation of C 60 within electron donor–acceptor conjugates by means of only photoexcitation.

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          Most cited references 16

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          Angew. Chem., Int. Ed.

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            25th anniversary article: 25 years of fullerene research in electron transfer chemistry.

            The past 25 years have served as a test bed for exploring the chemistry and physics, in general, and the electron transfer chemistry, in particular, of low-dimensional carbon. Nevertheless, the new realm started with the advent of fullerenes, followed in chronological order by carbon nanotubes, and, more recently, by graphene. The major thrust of this Review article is to historically recap the versatility of fullerenes regarding the design, the synthesis, and the tests as an electroactive building block in photosynthetic reaction mimics, photovoltaics, and catalysis.
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              J. Phys. Chem. Lett.

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                Author and article information

                Journal
                Chem Sci
                Chem Sci
                Chemical Science
                Royal Society of Chemistry
                2041-6520
                2041-6539
                1 July 2015
                16 April 2015
                : 6
                : 7
                : 4141-4147
                Affiliations
                [a ] Department of Chemistry and Pharmacy , Interdisciplinary Center for Molecular Materials (ICMM) , Friedrich-Alexander-Universität Erlangen-Nürnberg , 91058 Erlangen , Germany . Email: dirk.guldi@ 123456fau.de
                [b ] Department of Organic Chemistry , Autonoma University of Madrid , Cantoblanco , 28049 Madrid , Spain
                [c ] IMDEA Nanoscience , Faraday 9 , 28049 Madrid , Spain
                [d ] Interdepartamental Research Service (SIDI) , Lab. of High Resolution X-Ray Diffraction of Monocrystals , Autonoma University of Madrid , Cantoblanco , 28049 Madrid , Spain
                [e ] Life Science Center of Tsukuba Advanced Research Alliance , University of Tsukuba , 305-8577 Tsukuba , Japan
                [f ] College of Physics , Optoelectronics and Energy & Collaborative Innovation Center of Suzhou Nano Science and Technology , Soochow University , 215006 Suzhou , China
                [g ] Foundation for Advancement of International Science , 305-0821 Tsukuba , Japan
                [h ] Department of Chemistry , Tokyo Gakugei University , 184-8501 Koganei , Japan
                [i ] College of Materials Science and Engineering , Huazhong University of Science and Technology , 430074 Wuhan , China
                Article
                c5sc00223k
                10.1039/c5sc00223k
                5707453
                b9797361-79a2-42b4-ae5f-5e3520772c26
                This journal is © The Royal Society of Chemistry 2015

                This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)

                Categories
                Chemistry

                Notes

                †Electronic supplementary information (ESI) available. CCDC 1014106. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00223k

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