%0 Journal Article %A Loosli, Claudia %A Jia, Chunyang %A Liu, Shi-Xia %A Haas, Marco %A Dias, Marylène %A Levillain, Eric %A Neels, Antonia %A Labat, Gael %A Hauser, Andreas %A Decurtins, Silvio %T Synthesis and Electrochemical and Photophysical Studies of Tetrathiafulvalene-Annulated Phthalocyanines %J Journal of Organic Chemistry %@ 0022-3263 %V 70 %N 13 %P 4988-4992 %D 2005 %U http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/2005/70/i13/abs/jo0501801.html %R 10.1021/jo0501801 %U http://archive-ouverte.unige.ch/unige:3274 %X 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 π-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.