Photophysical and electrochemical studies of porphyrin containing ferrocene and/or fluorine

Abstract

Functionalized porphyrin and porphyrin containing trifluoromethyl with ferrocene were synthesized. The UV-Vis absorption bands of porphyrin with an electron withdrawing trifluoromethyl group were blue-shifted and those of porphyrin with an electron donating ferrocenyl group were red-shifted. The porphyrin containing ferrocenyl exhibited strong fluorescence quenching compared with those containing trifluoromethyl. The quenching efficiency of diferrocenyl porphyrin was about 66% with a quantum yield Φf of 0.08. These results indicated that there was a strong interaction between the excited state of porphyrin and ferrocene, which was further confirmed by the time-resolved fluorescence measurements. The electrochemical studies indicated that it was difficult to lost electron for the stable porphyrin with an electron withdrawing trifluoromethyl. However, the porphyrin with a ferrocenyl group was oxidized easily to lost electron and was a good electron donor. The research is supposed to provide some theoretical basis for this kind of compound using in donor-acceptor system. © 2013 Chinese Chemical Society and SIOC, CAS.