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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Teixeira Tasso, Thiago Silva, Artur M. S. Neves, M. Graça P. M. S. Uliana, Marciana P. Furuyama, Taniyuki Cavaleiro, José A. S. Menezes, José C. J. M. D. S. De Oliveira, Kleber T. Röder, Beate Hackbarth, Steffen Kobayashi, Nagao Ferreira, Vitor F. Faustino, M. Amparo F. |
| Description | Author Affiliation: Menezes JC ( Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro (Portugal), Fax: (+351)234-401-470.) |
| Abstract | In view of increasing demands for efficient photosensitizers for photodynamic therapy (PDT), we herein report the synthesis and photophysical characterizations of new $chlorin e_{6}$ trimethyl ester and protoporphyrin IX dimethyl ester dyads as free bases and $Zn^{II}$ complexes. The synthesis of these molecules linked at the β-pyrrolic positions to pyrano[3,2-c]coumarin, pyrano[3,2-c]quinolinone, and pyrano[3,2-c]naphthoquinone moieties was performed by using the domino Knoevenagel hetero Diels–Alder reaction. The α-methylenechromanes, α-methylenequinoline, and ortho-quinone methides were generated in situ from a Knoevenagel reaction of 4-hydroxycoumarin, 4-hydroxy-6-methylcoumarin, 4-hydroxy-N-methylquinolinone, and 2-hydroxy-1,4-naphthoquinone, respectively, with paraformaldehyde in dioxane. All the dyads as free bases and as $Zn^{II}$ complexes were obtained in high yields. All new compounds were fully characterized by 1D and 2D NMR techniques, UV/Vis spectroscopy, and HRMS. Their photophysical properties were evaluated by measuring the fluorescence quantum yield, the singlet oxygen quantum yield by luminescence detection, and also the triplet lifetimes were correlated by flash photolysis and intersystem crossing (ISC) rates. The fluorescence lifetimes were measured by a time-correlated single photon count (TCSPC) method, fluorescence decay associated spectra (FDAS), and anisotropy measurements. Magnetic circular dichroism (MCD) and circular dichroism (CD) spectra were recorded for one $Zn^{II}$ complex in order to obtain information, respectively, on the electronic and conformational states, and interpretation of these spectra was enhanced by molecular orbital (MO) calculations. Electrochemical studies of the $Zn^{II}$ complexes were also carried out to gain insights into their behavior for such applications. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 42 |
| Volume Number | 20 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2014-10-13 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Coordination Complexes Chemical Synthesis Photosensitizing Agents Porphyrins Protoporphyrins Zinc Chemistry Cycloaddition Reaction Electrochemical Techniques Methylation Spectrum Analysis Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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