Synthesis and electrochemical and photophysical studies of tetrathiafulvalene-annulated phthalocyanines |
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Authors: | Loosli Claudia Jia Chunyang Liu Shi-Xia Haas Marco Dias Marylène Levillain Eric Neels Antonia Labat Gael Hauser Andreas Decurtins Silvio |
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Affiliation: | Departement für Chemie und Biochemie, Universit?t Bern, Freiestrasse 3, 3012 Bern, Switzerland. |
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Abstract: | The synthesis of tetrakis(tetrathiafulvalene)-annulated metal-free and metallophthalocyanines 5-8 via the tetramerization of the phthalonitrile derivative 4 is reported. All of them have been fully characterized by electronic absorption spectroscopy, thin-layer cyclic voltammetry, mass spectrometry, and elemental analysis. Their solution electrochemical data show two reversible four-electron oxidation waves, indicating that these fused systems are strong pi-electron donors, which give rise to tetra- or octaradical cation species. For the metal-free phthalocyanine 5, additionally a reversible one-electron wave was found in the negative direction arising from the reduction of the macrocycle. Moreover, the tetrathiafulvalene unit acts as an efficient reductive electron-transfer quencher for the phthalocyanine emission, but upon its oxidation, an intense luminescence is switched on. |
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