Synthesis, spectroscopy and electrochemistry of phthalocyanine derivatives functionalised with four and eight peripheral tetrathiafulvalene units
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.
) 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.
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