Abstract
A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C60 and PyC60 (a pyridyl [60]fulleropyrrolidine) were evaluated by absorption and fluorescence titrations in toluene. While no measurable modifications of the absorption and fluorescence spectra were observed upon addition of C60 to the porphyrin derivatives, the addition of PyC60 to the corresponding mono-Zn(II) porphyrins resulted in the formation of Zn(porphyrin)–PyC60 coordination complexes and the binding constants were calculated. Results show that the four free-base porphyrin units in pentaporphyrin 6 have a significant contribution in the stabilization of the 6–PyC60 complex. The crystal and molecular features of the pentaporphyrin Zn5 were unveiled using single-crystal X-ray diffraction studies.
Highlights
Porphyrins are extremely versatile compounds from structural and chemical viewpoints.They display a rigid planar geometry, high stability, intense electronic absorption and emission, a small HOMO–LUMO energy gap, and flexible tunability of their optical and redox properties by changing the metal center [1]
We have shown that 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin (1) reacts as a nucleophile with hexafluorobenzene or pentafluorophenyl groups to give multiporphyrin derivatives under very mild conditions [67]
Titrations with PyC60 lead to the formation of Zn(porphyrin)–PyC60 coordination complexes and the corresponding binding constants were calculated
Summary
Porphyrins are extremely versatile compounds from structural and chemical viewpoints.They display a rigid planar geometry, high stability, intense electronic absorption and emission, a small HOMO–LUMO energy gap, and flexible tunability of their optical and redox properties by changing the metal center [1]. Several synthetic strategies have been developed to produce multiporphyrin oligomers, including directly meso–meso-, meso–β- and β–β-linked multiporphyrin systems, oligoporphyrins with fused π-systems and arrays bearing rigid or flexible spacers In this context, different types of covalent or supramolecular porphyrin arrays with a large structural diversity [19,20,21,22], including linear [23,24,25], zig-zag [26], and dendritic arrays [27,28], tapes [29,30,31], belts [32], barrels [33], rings [34,35,36,37,38,39,40,41,42,43,44] and boxes [45] and balls [46], have been synthesized
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