Mechanism of Interaction of  -Halogenated Salts of Pyrylium and Benzopyrylium with Aromatic Amines

Manyashin, A. O.; Fomenko, A. I.; Storozhenko, V. N.; Берберова, Н. Т.

doi:10.1023/b:ruel.0000003453.71265.a2

Cited by 2 publications

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“…Concurrently, the anodic waves at the most negative potentials during scans between 0 and 2 V vs. SCE in the absence of TFA most plausibly correspond to the reduction of the deprotonated dyes, PF-X . The former assignment agrees with reported reduction potentials of flavylium ions that range between about 0 and −0.5 V vs. Ag/AgCl [ 70 ] and are on par with reduction potentials of quinones [ 55 , 57 , 71 ]. The latter is consistent with ascribing the observed anodic waves to the oxidation of quinoidal forms of hydroxyflavylium dyes [ 35 , 69 ].…”

Section: Resultssupporting

confidence: 89%

Photophysics and Electrochemistry of Biomimetic Pyranoflavyliums: What Can Bioinspiration from Red Wines Offer

et al. 2022

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Natural dyes and pigments offer incomparable diversity of structures and functionalities, making them an excellent source of inspiration for the design and development of synthetic chromophores with a myriad of emerging properties. Formed during maturation of red wines, pyranoanthocyanins are electron-deficient cationic pyranoflavylium dyes with broad absorption in the visible spectral region and pronounced chemical and photostability. Herein, we survey the optical and electrochemical properties of synthetic pyranoflavylium dyes functionalized with different electron-donating and electron-withdrawing groups, which vary their reduction potentials over a range of about 400 mV. Despite their highly electron-deficient cores, the exploration of pyranoflavyliums as photosensitizers has been limited to the “classical” n-type dye-sensitized solar cells (DSSCs) where they act as electron donors. In light of their electrochemical and spectroscopic properties, however, these biomimetic synthetic dyes should prove to be immensely beneficial as chromophores in p-type DSSCs, where their ability to act as photooxidants, along with their pronounced photostability, can benefit key advances in solar-energy science and engineering.

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Section: Resultssupporting

confidence: 89%

Photophysics and Electrochemistry of Biomimetic Pyranoflavyliums: What Can Bioinspiration from Red Wines Offer

et al. 2022

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Azulene‐substituted pyranylium salts. Syntheses and products characterization

Razus

Bîrzan

Pavel

et al. 2006

Journal of Heterocyclic Chem

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Azulene-substituted Pyranylium Salts. Syntheses and Products Characterization 965Structure of azulen-1-yl pyranylium salts. A biphenyllike isomerism of azulenyl pyranylium salts can be predicted due to the short distance, (C Az -C Py ), between the two moieties mainly when the system has bulky groups substituted in the proper positions. A useful tool for structure assignment was considered the computation (with MOPAC and PCMODEL method) [16] of the dihedral angle, ( ), and (C Az -C Py ) bond length and also of the energy barrier to rotation (racemization); the calculated values are given in Table 1 and 2. Assuming that better conjugation results from shorter bond lengths, the calculated values for C Az -C Py length indicate that the conjugation between 4-pyranylium and 1-azulene is stronger than that with benzene or 1-naphthalene. The increase of the angle in order azulene < phenyl < naphthyl results from the greater electron donating character of the azulenyl moiety, which stabilizes the positive charge of the 4-pyranylium moiety.

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Mechanism of Interaction of -Halogenated Salts of Pyrylium and Benzopyrylium with Aromatic Amines

Cited by 2 publications

References 3 publications

Photophysics and Electrochemistry of Biomimetic Pyranoflavyliums: What Can Bioinspiration from Red Wines Offer

Photophysics and Electrochemistry of Biomimetic Pyranoflavyliums: What Can Bioinspiration from Red Wines Offer

Azulene‐substituted pyranylium salts. Syntheses and products characterization

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