Synthesis of a fluorescein–porphyrin hybrid and its supramolecular self-assembly with amino-porphyrinatocopper(II) by hydrogen bonding

Abstract

A fluorescein-porphyrin hybrid (Fl-PTPP) has been synthesized and characterized by UV/Vis, IR, 1 H NMR, ES-MS and elemental analysis. The supramolecular selfassembly of Fl-PTPP with the copper(II) complex of 5-(p-amino-phenyl)-10,15,20-triphenylporphyrin, (CuAPTPP), by hydoxyl-amino type hydrogen bonding was studied using vapor pressure osmometry (VPO) measurements, ES-MS, UV/Vis, 1 H NMR and fluorescence spectroscopic titration. The data indicate formation of a (Fl-PTPP)-CuAPTPP supramolecular complex. Fluorescence strengthening character was observed in a spectroscopic titration experiment for the Fl-PTPP/CuAPTPP system. The association constant of the supramolecular complex was calculated from the fluorescence titration data, and found to be less than that of a carboxyl-carboxyl type hydrogen-bonding system.

Synthesis, characterization and photophysical studies of ß-triazolomethyl-bridged porphyrin-benzo- a-pyrone dyads

“…4 Additionally, these molecules have been widely used in the study of various charge-transfer 5 and energy-transfer 6 processes. In the past decades, a large number of porphyrinoids linked with various π-electron rich and biologically relevant chromophores including anthracene, 7 anthraquinone, 8 fluorescein, 9 perylene, 10 fluorene, 11 pyrrolo [1,2-a]quinoxaline, 12 coumarin, 13 quinoline, 14 imidazole, 15 thiazole, 16 and pyrazole 17 have been synthesized through peripheral functionalization involving mesoand β-positions of meso-tetraarylporphyrins. Among these, the β-substituted porphyrins often demonstrate interesting electronic properties because of direct conjugation of attached scaffold with the 18π-macrocyclic system.…”