Porphyrin Macrocycle Modification: Pyrrole Ring-Contracted or -Expanded Porphyrinoids

Costa, Letícia D.; Costa, Joana I. T.; Tomé, Augusto C.

doi:10.3390/molecules21030320

Cited by 54 publications

(34 citation statements)

References 116 publications

(151 reference statements)

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“…The unique physical-chemical properties displayed by porphyrins are responsible for the promising potentialities of these compounds as catalysts, sensors, in the development of electronic devices and for solar cells production [1][2][3]. These compounds are considered to be highly relevant in the medicinal field due to their high ability to act as photosensitizers in photodynamic therapy (PDT) [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

et al. 2020

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Novel triazole-porphyrin derivatives (TZ-PORs) were synthesized through the Heck reaction and then incorporated into polyvinylpyrrolidone (PVP) micelles. After verifying that this incorporation did not compromise the photophysical and chemical features of TZ-PORs as photosensitizers, the phototoxicity of the formulations towards cancer cells was screened. Biological studies show high photodynamic activity of all PVP-TZ-POR formulations against a bladder cancer cell line with a particular highlight to PVP-TZ-POR 7e and 7f that are able to significantly reduce HT-1376 cell viability, while they had no effect on control ARPE-19 cells.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

et al. 2020

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“…Therefore the changes in the conjugated system, symmetry and geometry of the porphyrins, which can affect the corresponding UV-Vis spectrum [58]. Moreover, according to the results of the TD-DFT calculations, Fig.…”

Section: Electronic Absorption Spectramentioning

confidence: 97%

The role of the electronic structure and solvent in the dye-sensitized solar cells based on Zn-porphyrins: Theoretical study

Arkan

Izadyar

Nakhaeipour

2016

Energy

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In this work, using the density functional theory (DFT) and time-dependent DFT (TD-DFT), we have theoretically studied the electronic structures, quantum reactivity parameters and absorption spectra of the several dyes based on Zn-porphyrin derivatives in the gas phases, methanol (MeOH) and tert-buthanol (t-BuOH). Also, open-circuit photovoltage (V OC), exciton binding energy (EBE), light harvesting efficiency (LHE), the free energy change of regeneration (∆G regen. (d y e)), and the free energy change of electron injection (∆G inject) have been investigated. The studied dyes in the presence of the solvents showed a smaller gap of the highest occupied molecular orbital (HOMO)the lowest unoccupied molecular orbital (LUMO) and lower EBE, a higher intensity and oscillator strength and red shift in the absorption spectra. These changes facilitate the charge transfer (CT) phenomena in the nano-structures of the dyes and improve the solar cell efficiency. Chemical modifications of the dyes by electron donor groups or conjugated system extension, improve the incident photon to current conversion efficiency (IPCE), the energy gap between the LUMO of the dye and the conduction band (CB) of the TiO 2 (eV OC), and the LHE of these dye-sensitized solar cells (DSSCs). Finally, some correlations between the molecular descriptors and solar cell parameters were analyzed.

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“…Replacement of pyrrole rings in a porphyrin framework with non‐pyrrolic units is often a powerful means to create novel porphyrin analogues called as pyrrole‐modified porphyrins (PMPs) . The chemistry of PMPs started by the synthesis of oxazolochlorin by Fischer and Malden in 1933 .…”

Section: Introductionmentioning

confidence: 99%

Pyrrole‐Modified Subporphyrins Bearing a Sulfur‐Containing Heterocyclic Unit

Yoshida

Osuka

2018

Helvetica Chimica Acta

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As new pyrrole‐modified subporphyrins (PMSubPs) bearing a sulfur‐containing heterocyclic unit, dithiazolosubporphyrin 5, dithiazinosubchlorin 6, and oxodithiazinosubchlorin 7 were synthesized from α‐fluorosubchlorophin 2 via α’‐selective nitration with Cu(NO3)2 followed by double SN2 reaction with methyl 3‐mercaptopropionate as a key step. Oxidation of 5 with H2O2 in the presence of a tungsten catalyst afforded S,S‐dioxodithiazolosubporphyrin 8 and nitration of 5 with Cu(NO3)2·3H2O gave β‐nitrodithiazolosubporphyrin 9 or β,β‐dinitrodithiazolosubporphyrins 10a and 10b depending on reaction conditions. In the solid‐states, the dithiazole units in 8 and 9 are almost planar but the dithiazine unit in 6 and the 2‐oxodithiazine unit in 7 are non‐planar. Compared to subchlorophin 1, dithiazolosubporphyrin 5 possesses a significantly reduced diatropic ring current and a greatly perturbed absorption spectrum showing largely split Q‐like bands at 501 and 660 nm. These perturbed electronic and optical properties of 5 are considerably attenuated in 6 and 7 and completely vanished in 8, suggesting the importance of disulfide bond for the large perturbation.

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Porphyrin Macrocycle Modification: Pyrrole Ring-Contracted or -Expanded Porphyrinoids

Cited by 54 publications

References 116 publications

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

Synthesis, Characterization and Photodynamic Activity against Bladder Cancer Cells of Novel Triazole-Porphyrin Derivatives

The role of the electronic structure and solvent in the dye-sensitized solar cells based on Zn-porphyrins: Theoretical study

Pyrrole‐Modified Subporphyrins Bearing a Sulfur‐Containing Heterocyclic Unit

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