Amphiphilic meso(sulfonate ester fluoroaryl)porphyrins: refining the substituents of porphyrin derivatives for phototherapy and diagnostics

A set of amphiphilic fluorinated porphyrins appended with sulfonate ester groups were synthesized and fully characterized. The reaction proceeds efficiently, with high yields, with an improved methodology. Their potential use as imaging and phototherapeutic agents was assessed measuring relevant photophysical properties. It is shown that these porphyrins have good photostability, long triplet lifetimes (between 47 mu s and 102 mu s), high singlet oxygen quantum yields (0.74 <= FD <= 1.00), low fluorescence quantum yields (<0.04) and sharp 19F NMR peaks. The data on the new meso(sulfonate ester fluoroaryl) porphyrins illustrate the potential of perfluorinated sulfonate esters to improve physical properties relevant for cancer imaging and photodynamic therapy. (C) 2012 Elsevier Ltd. All rights reserved.