A theoretical investigation on the spectroscopic properties and photosensitizing capability of 5, 10, 15, 20-tetraphenylsapphyrin and 5, 10, 15, 20-tetraphenyl-26,28-diheterosapphyrins with two O, S, or Se Atoms

López, Raḿon; Menéndez, María Isabel Menéndez; Santander-Nelli, Mireya; Cárdenas-Jirón, Gloria I.

doi:10.1007/s00214-010-0735-5

Cited by 14 publications

(11 citation statements)

References 74 publications

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“…[12] Since then, sapphyrins have remained at opic of high interest, [13][14][15][16] in part because of their potential applicationsi nt he area of photodynamic therapy and their structurals imilarity to the well-known porphyrin and corrole macrocycles, [10,11,[17][18][19][20][21] and in part because of their unique properties as ar eceptor of neutraland anionic substrates. [22][23][24][25][26][27][28][29] Al arge number of studies have characterizedd ifferent sapphyrind erivatives, including b-alkylateds apphyrins, [30][31][32][33] coremodified sapphyrins with heteroatoms (O, S, or Se), [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] Nfused/N-confused sapphyrins, [51][52][53][54] and meso-tetraaryl-substituted sapphyrins. [55]…”

Section: Introductionmentioning

confidence: 99%

“…A large number of studies have characterized different sapphyrin derivatives, including β‐alkylated sapphyrins, core‐modified sapphyrins with heteroatoms (O, S, or Se), N‐fused/N‐confused sapphyrins, and meso ‐tetraaryl‐substituted sapphyrins . Sapphyrins containing four meso ‐aryl substituents can serve as favorable building blocks for the further design of molecules, which are similar to meso ‐aryl‐substituted porphyrins, whose redox properties and chemical reactions can be finely tuned .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Electrochemistry of Open‐Chain Pentapyrroles and Sapphyrins with Highly Electron‐Withdrawing meso‐Tetraaryl Substituents

Shan

Desbois

Blondeau-Pâtissier

et al. 2017

Chemistry A European J

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A series of open-chain pentapyrroles and sapphyrins with highly electron-withdrawing substituents (i.e., CN, CF , or CO Me) on the meso-phenyl rings was synthesized and characterized as to the spectral properties, protonation reactions, and electrochemistry in non-aqueous media. The investigated compounds are represented as (Ar) PPyH and (Ar) SapH where PPy and Sap correspond to the tri-anion of the open-chain pentapyrrole and sapphyrin, respectively, and Ar=p-CNPh, p-CF Ph, or p-CO MePh. UV/Vis and H NMR spectroscopy as well as mass spectrometry data are given for the confirmation of the structures for the newly synthesized compounds. An X-ray structure for one of the pentapyrroles, that is, (p-CF Ph) PPyH (2), is also presented. The protonation processes were examined by UV/Vis absorption spectroscopy during the titration of the compounds with trifluoroacetic acid (TFA) in CH Cl . Equilibrium constants for the protonation reactions were calculated by using both the Hill equation and the mole ratio method. The protonation-initiated conversion of pentapyrroles to sapphyrins upon oxidation was also investigated. Cyclic voltammetry was used to measure the redox potentials in CH Cl , PhCN, and/or pyridine (Py). Electrochemical properties, protonation constants, and chemical reactions of the six compounds in the two series were then analyzed as a function of the solvent properties and the type of the electron-withdrawing groups on the meso-phenyl rings.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Electrochemistry of Open‐Chain Pentapyrroles and Sapphyrins with Highly Electron‐Withdrawing meso‐Tetraaryl Substituents

Shan

Desbois

Blondeau-Pâtissier

et al. 2017

Chemistry A European J

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“…Most investigated sapphyrins have contained coremodified macrocycles with O, S or Se heteroatoms [19][20][21][22][23][24][25][26][27][28][29][30][31], but a few N-5 meso-tetraaryl-substituted sapphyrins have been isolated as side-products in the synthesis of porphyrins [32,33] or directly synthesized by oxidation of an open-chain pentapyrrole in trifluoroacetic acid (TFA)/I 2 in solutions of benzene or toluene [34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

A facile synthetic route to meso-tetraaryl substituted N-5 sapphyrins and first single crystal X-ray analysis confirming the pyrrole inverted structure

Huang

Chen

et al. 2015

J. Porphyrins Phthalocyanines

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Three meso-tetraaryl substituted N-5 sapphyrins were synthesized by a facile synthetic route from the corresponding open-chain pentapyrroles in high yield using acetic acid as the solvent and catalyst. Each compound was characterized by spectroscopic and electrochemical methods and the inverted pyrrole structure was confirmed in the solid state for the first time by single crystal X-ray analysis. A FACILE SYNTHETIC ROUTE TO MESO-TETRAARYL SUBSTITUTED N-5 SAPPHYRINS 7 R indices (all data) R1 = 0.1552, wR2 = 0.2574 J. Porphyrins Phthalocyanines Downloaded from www.worldscientific.com by UNIVERSITY OF CALIFORNIA @ SAN DIEGO on 06/03/15. For personal use only.

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“…Structural view including the atom numbering of sapphyrin. (Reproduced with permission from Springer …”

Section: Quantum Chemical Studies and Potential Applicationsmentioning

confidence: 99%

“…Sapphyrin (5,10,15,20‐tetraphenylsapphyrin, TPS) and three disubstituted derivatives (with O, S, or Se atoms) (TP2OS, TP2SS, and TP2SeS) were investigated as potential photosensitizers in PDT using DFT (see Figure ) . In a previous work, we proposed several reasons for the greater stability of the inverted (i) conformation of TPS and TP2OS, and the normal (n) conformation of TP2SS and TP2SeS .…”

Section: Quantum Chemical Studies and Potential Applicationsmentioning

confidence: 99%

Quantum chemical studies of porphyrin‐ and expanded porphyrin‐based systems and their potential applications in nanoscience. Latin America research review

Cárdenas-Jirón

Borges-Martínez

Mera‐Adasme

et al. 2018

Int J of Quantum Chemistry

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Porphyrins and expanded porphyrins are fascinating molecular structures, and its wide applicability in different fields of the nanoscience has produced an extensive number of scientific publications. The purpose of this article is to review the research performed on porphyrins and expanded porphyrins in the Latin American region at a theoretical level of quantum chemistry using different methodologies available. The present review is organized considering the most important applications that these molecular systems have found. In this way, we classify the reported works in the following fields studied by the nanoscience: molecular electronics, dye‐sensitized solar cells, and photodynamic therapy. Because of its relevance, we also highlight other reports focused on the topological analysis of the electron density and aromaticity. Current investigation on these topics applied to porphyrin‐ and expanded porphyrin‐based systems and the future perspective in this field are presented.

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A theoretical investigation on the spectroscopic properties and photosensitizing capability of 5, 10, 15, 20-tetraphenylsapphyrin and 5, 10, 15, 20-tetraphenyl-26,28-diheterosapphyrins with two O, S, or Se Atoms

Cited by 14 publications

References 74 publications

Synthesis, Characterization, and Electrochemistry of Open‐Chain Pentapyrroles and Sapphyrins with Highly Electron‐Withdrawing meso‐Tetraaryl Substituents

Synthesis, Characterization, and Electrochemistry of Open‐Chain Pentapyrroles and Sapphyrins with Highly Electron‐Withdrawing meso‐Tetraaryl Substituents

A facile synthetic route to meso-tetraaryl substituted N-5 sapphyrins and first single crystal X-ray analysis confirming the pyrrole inverted structure

Quantum chemical studies of porphyrin‐ and expanded porphyrin‐based systems and their potential applications in nanoscience. Latin America research review

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