Synthesis, spectroscopy and electrochemistry of phthalocyanine derivatives functionalised with four and eight peripheral tetrathiafulvalene units
- 1 January 1997
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 9,p. 1671-1678
- https://doi.org/10.1039/a701703k
Abstract
Metal-free phthalocyanine derivatives 2 and 14 bearing eight and four peripheral tetrathiafulvalene (TTF) units, respectively, have been synthesised, and their solution electrochemistry and optical spectroscopy have been studied. The compounds display redox properties arising from the TTF and from the phthalocyanine groups. 1H NMR and UV–VIS spectroscopic studies in solution show that aggregation is strongly solvent dependent. Quenching of the fluorescence of the phthalocyanine core by the TTF units was observed. The X-ray crystal structure of 4,5-bis(hexylthio)-4′,5′-bis(hydroxymethyl)-TTF 11, which was synthesised during the course of this work, has been determined. The hydroxy groups of 11 engage in intermolecular (and interstack) hydrogen bonds. Computer modelling studies on phthalocyanine derivatives 2 and 14 are reported.Keywords
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