A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine

abstract

A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C-60 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 C-60 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.

keywords

TEMPLATE-DIRECTED SYNTHESIS; ELECTRON-TRANSFER; PHOTOPHYSICAL PROPERTIES; PORPHYRIN ARRAYS; ENERGY-TRANSFER; PI-PI; CORANNULENE; HOSTS; ARCHITECTURES; CHEMISTRY

subject category

Biochemistry & Molecular Biology; Chemistry

authors

Costa, JIT; Farinha, ASF; Paz, FAA; Tome, AC

our authors

acknowledgements

This research was funded by Fundacao para a Ciencia e a Tecnologia (FCT), through project PTDC/QEQ-QOR/6160/2014 and the research units UID/QUI/00062/2019 and UID/CTM/50011/2019.

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