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| hree novel tetrathiafluvalene-annulated metalloporphyrazine dyes with electron-
withdrawing pentoxycarbonyl groups at periphery were synthesized via a cyclotetramerization of dipentyl 6,7-dicyanotetrathiafulvalen-2,3-dicarboxylate in the presence of corresponding metal salts (Zn(OAc)2•2H2O, Cu(OAc)2•2H2O, and NiCl2) in pentanol and the structures were fully characterized by 1H-NMR, FT-IR, UV-vis, MULDI-TOF mass spectra and elemental analysis. The newly synthesized macrocyclic dyes are sufficiently air-stable for the purification process, where the electron-withdrawing substituents reduced the propensity to form the radical cation of tetrathiafulvalene groups . Their solution electrochemical data show one reductive and three oxidative processes within -2000 mV to +2200 mV potential window. Four couples can be assigned to Pz-2/Pz-3 (I), TTF+•/TTF (II), TTF+2/ TTF+• (III), and Pz-1/Pz-2 (IV).
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| Keywords:dye; tetrathiafulvalenedinitrile;metalloporphyrazines;electrochemistry;aggregation |
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