title: Synthesis and electrochemical and photophysical studies of tetrathiafulvalene-annulated phthalocyanines.
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.
authors.affiliation: Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland.
authors.forename: Claudia
authors.initials: C
authors.lastname: Loosli
authors.forename: Chunyang
authors.initials: C
authors.lastname: Jia
authors.forename: Shi-Xia
authors.initials: SX
authors.lastname: Liu
authors.forename: Marco
authors.initials: M
authors.lastname: Haas
authors.forename: Marylène
authors.initials: M
authors.lastname: Dias
authors.forename: Eric
authors.initials: E
authors.lastname: Levillain
authors.forename: Antonia
authors.initials: A
authors.lastname: Neels
authors.forename: Gael
authors.initials: G
authors.lastname: Labat
authors.forename: Andreas
authors.initials: A
authors.lastname: Hauser
authors.forename: Silvio
authors.initials: S
authors.lastname: Decurtins