Synthesis and electrochemical and photophysical studies of tetrathiafulvalene-annulated phthalocyanines.
- Loosli C Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland.
- Jia C
- Liu SX
- Haas M
- Dias M
- Levillain E
- Neels A
- Labat G
- Hauser A
- Decurtins S
- 2005-06-18
Published in:
- The Journal of organic chemistry. - 2005
English
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.
- Language
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- English
- Open access status
- green
- Identifiers
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- DOI 10.1021/jo0501801
- PMID 15960496
- Persistent URL
- https://sonar.rero.ch/global/documents/79462
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