Spectroscopic and Theoretical Investigations on Supramolecular Interaction of a Newly Designed Monoporphyrin with Fullerenes and Functionalized Fullerenes in Solution

摘要

The present paper reports the results of a photophysical investigation of a designed monoporphyrin (1) and its supramolecular complexes with C60, C70 and derivatized fullerenes, namely tert-butyl-(1,2-methanofullerene)-61-carboxylate (2) and [6,6]-phenyl C71 butyric acid methyl ester (3) in toluene. UV–vis studies reveal appreciable ground state interaction between the fullerenes and compound 1. Steady state fluorescence studies show quenching of fluorescence of 1 in the presence of fullerenes. The binding constants of the C60/1, C70/1, 2/1 and 3/1 complexes are estimated to be 300, 20770, 1150 and 13170 dm3⋅mol−1, respectively. Molecular mechanics calculations in vacuo evoke the stereoscopic structures of the fullerene/1 complexes and allow interpretation of the stability difference among various fullerene complexes of 1 in terms of their enthalpies of formation.