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Synthesis and photophysical evaluation of meso-phenyl-1,4-dihydropyridineand pyridine-porphyrin hybrids

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Departamento de Farmácia, Universidade Federal do Paraná, Av. Lothario Meissner, 3400, Jardim Botânico, Curitiba, Paraná, Brazil

    Lais Danciguer Guanaes, Matheus Murmel Guimarães, Sandra M. W. Barreira & Alan Guilherme Gonçalves

  2. Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, P. O. Box 19046, Curitiba, Paraná, Brazil

    Diogo R. B. Ducatti, Maria Eugênia R. Duarte & Miguel D. Noseda

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  1. Lais Danciguer Guanaes
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  2. Matheus Murmel Guimarães
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  3. Diogo R. B. Ducatti
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Correspondence to Alan Guilherme Gonçalves.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(12), 1195–1203

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Guanaes, L.D., Guimarães, M.M., Ducatti, D.R.B. et al. Synthesis and photophysical evaluation of meso-phenyl-1,4-dihydropyridineand pyridine-porphyrin hybrids. Chem Heterocycl Comp 57, 1195–1203 (2021). https://doi.org/10.1007/s10593-021-03043-w

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