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- Title
Synthesis and photophysical evaluation of meso-phenyl-1,4-dihydropyridineand pyridine-porphyrin hybrids.
- Authors
Guanaes, Lais Danciguer; Guimarães, Matheus Murmel; Ducatti, Diogo R. B.; Duarte, Maria Eugênia R.; Barreira, Sandra M. W.; Noseda, Miguel D.; Gonçalves, Alan Guilherme
- Abstract
In the present work, we have synthesized new molecular hybrids consisting of porphyrin ring system connected at the meso positions with phenyl groups and/or, through p-phenylene linkers, with 1,4-dihydropyridine or pyridine moieties. In general, the directed use of dihydropyridine aldehyde, under time-modified Adler–Longo procedures, gave the best overall yields of the following meso-substituted dihydropyridine-porphyrins of general formula A1B3, A2B2, or A4, where A stands for phenyl-dihydropyridine and B for phenyl substituents. The corresponding meso-substituted pyridine-porphyrin hybrids were obtained from oxidation of the dihydropyridineporphyrins with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The UV-vis spectra bands of the A4 dihydropyridine-porphyrin were unexpectedly red-shifted, having a rhodoporphyrin Q-bands profile. It was also found that an increased production of 1O2 correlates with a higher number of dihydropyridine or pyridine moieties in the hybrid molecule. All porphyrin hybrids were considered adequate candidates to be employed in photodynamic therapy.
- Subjects
ZINC porphyrins; PHENYL group; PHOTODYNAMIC therapy; DIHYDROPYRIDINE; PYRIDINE; MOIETIES (Chemistry)
- Publication
Chemistry of Heterocyclic Compounds, 2021, Vol 57, Issue 12, p1195
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-021-03043-w