Synthesis and Spectroscopic Characterization of Two Tetrasubstituted Cationic Porphyrin Derivatives

Molecules

Antonio E.H. Machado¹  Weverson R. Gomes¹  Diesley M.S. Araújo¹  Hércules S. Miglio¹  Leonardo T. Ueno¹  Rodrigo De Paula¹  José A.S. Cavaleiro¹ 

[1] ¹Laboratório de Fotoquímica, Instituto de Química, Universidade Federal de Uberlândia, P.O. Box 593, CEP 38400-902 Uberlândia, Minas Gerais, Brazil

关键词: cationic porphyrin derivatives;    MAOS;    UV-Vis spectroscopy;    fluorescence spectroscopy;    DFT and TD-DFT;    electronic states;    solvent effects;   

DOI  :  10.3390/molecules16075807

来源: mdpi

【 摘 要 】

An imidazolium tetrasubstituted cationic porphyrin derivative (the free base and its Zn(II) complex) with five-membered heterocyclic groups in the meso-positions were synthesized using microwave irradiation, and the compounds obtained characterized by ¹H-NMR and mass spectrometry. We observed that under microwave irradiation the yield is similar to when the synthesis is performed under conventional heating, however, the time required to prepare the porphyrins decreases enormously. In order to investigate the electronic state of these compounds, we employed UV-Vis and fluorescence spectroscopy combined with quantum chemical calculations. The results reveal the presence, in both compounds, of a large number of electronic states involving the association between the Soret and a blue-shifted band. The Soret band in both compounds also shows a considerable solvent dependence. As for emission, these compounds present low quantum yield at room temperature and no solvent influence on the fluorescence spectra was observed.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.