An easy access to porphyrin triads and their supramolecular interaction with a pyridyl [60]fulleropyrrolidine

摘要

New porphyrin triads were synthesized through nucleophilic aromatic substitution of fluorine atoms of hexafluorobenzene by porphyrins containing nucleophilic groups (C6H4NH2 and C6H4OH) at the meso positions. The supramolecular interaction between triads 4 and 5 and a pyridyl [60]fulleropyrrolidine (PyC60) was investigated by absorption and fluorescence titrations in toluene. The results revealed that triad 5 forms a 1:1 complex with PyC60 whereas no interaction was observed between the metal-free triad 4 and PyC60. The binding constant for the 5 PyC60 complex is 1.5 times higher than the binding constant for the precursor Zn2, suggesting that, in addition to the axial coordination, the pi-pi interactions between the two free-base porphyrin units and the fullerene are also relevant for the stability of the 5 -PyC60 complex. (C) 2016 Elsevier Ltd. All rights reserved.