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Synthesis and Spectroscopic Characterization of Two Tetrasubstituted Cationic Porphyrin Derivatives
Laboratório de Fotoquímica, Instituto de Química, Universidade Federal de Uberlândia, P.O. Box 593, CEP 38400-902 Uberlândia, Minas Gerais, Brazil
Centro de Ciências Agrárias, Universidade Federal do Espírito Santo, Alegre, Espírito Santo, Brazil
Faculdade de Ciências Integradas do Pontal, Universidade Federal de Uberlândia, Ituiutaba, Minas Gerais, Brazil
Centro de Formação de Professores, Universidade Federal do Recôncavo da Bahia, Amargosa, Bahia, Brazil
Departamento de Química,Universidade de Aveiro, Aveiro, Portugal
Instituto de Física, Universidade Federal de Uberlândia, P.O. Box 593; CEP 38400-902 Uberlândia, Minas Gerais, Brazil
* Author to whom correspondence should be addressed.
Received: 17 April 2011; in revised form: 6 July 2011 / Accepted: 7 July 2011 / Published: 8 July 2011
Abstract: 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.
Keywords: cationic porphyrin derivatives; MAOS; UV-Vis spectroscopy; fluorescence spectroscopy; DFT and TD-DFT; electronic states; solvent effects
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Machado, A.E.; Gomes, W.R.; Araújo, D.M.; Miglio, H.S.; Ueno, L.T.; Paula, R.D.; Cavaleiro, J.A.; Neto, N.M.B. Synthesis and Spectroscopic Characterization of Two Tetrasubstituted Cationic Porphyrin Derivatives. Molecules 2011, 16, 5807-5821.
Machado AE, Gomes WR, Araújo DM, Miglio HS, Ueno LT, Paula RD, Cavaleiro JA, Neto NMB. Synthesis and Spectroscopic Characterization of Two Tetrasubstituted Cationic Porphyrin Derivatives. Molecules. 2011; 16(7):5807-5821.
Machado, Antonio E.H.; Gomes, Weverson R.; Araújo, Diesley M.S.; Miglio, Hércules S.; Ueno, Leonardo T.; Paula, Rodrigo De; Cavaleiro, José A.S.; Neto, Newton M. Barbosa. 2011. "Synthesis and Spectroscopic Characterization of Two Tetrasubstituted Cationic Porphyrin Derivatives." Molecules 16, no. 7: 5807-5821.