Lead (II) pyridyloxyphthalocyanine (PbTpyPc) and its quaternized form (PbTepyPc) were synthesized and the photophysical behavior examined. Low fluorescence quantum yields (Phi(F)) of 0.01 and 0.02 were observed for PbTepyPc and PbTpyPc, respectively. The singlet oxygen quantum yields (Phi(Delta)) were 0.60 and 0.68, for PbTepyPc and PbTpyPc, respectively using DPBF as a quencher in DMF. Singlet oxygen production of the embedded sensitizers in electrospun fiber were quantified using ADMA and were found to be Phi(Delta) = 0.41 and Phi(Delta) = 0.21 for PbTepyPc and PbTpyPc, respectively. Photodynamic inactivation of Escherichia coli (E. con) with the quaternized photosensitizer at 5 mu M, totally inactivated the E. coli (with log CFU = 10 decrease). Only 0.4 log CFU decrease was obtained with PbTpyPc. The embedded non-quaternized photosensitizer (PbTpyPc) was less active on the gram negative bacteria but the quaternized photosensitizer (PbTepyPc) was effective towards inactivation of E. coli. (C) 2014 Elsevier Ltd. All rights reserved.