DFT Evaluation of Reactivity of β-Substituted meso-Bromoporphyrins towards Nucleophilic Substitution

Birin, Kirill P.; Gorbunova, Yulia G.; Tsivadze, A. Yu.

doi:10.6060/mhc180280b

MHC

2018

DOI: 10.6060/mhc180280b

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DFT Evaluation of Reactivity of β-Substituted meso-Bromoporphyrins towards Nucleophilic Substitution

Kirill P. Birin¹,

Yulia G. Gorbunova²,

A. Yu. Tsivadze³

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2023

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Cited by 2 publications

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“…Previously we attempted to rationalize the influence of the electronic properties of meso-and substituents on the distribution and energy levels of the porphyrin frontier orbitals for the prediction of their reactivity. [44,45] It was clearly observed that orbital structure of the porphyrin macrocycle is notably less sensitive to substitution pattern, compared to meso-substitution.…”

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confidence: 99%

Efficient Approach to Functionalized β-Imidazolylporphyrins

Polivanovskaia,

Shremzer,

Voronova

et al. 2023

MHC

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The applicability of the Debus-Radziszewski condensation of 2-formylporphyrins with aromatic -diketones for the straightforward preparation of 2-functionalized porphyrin derivatives by means of the imidazole heterocyclic bridging unit was investigated in details. The successful transformation of the starting materials was observed regardless the meso-substitution pattern of the porphyrin macrocycle. In contrast, the reactivity and stability of the aromatic -diketone is revealed to possess considerable influence onto the reaction path. Thus, the application of phenanthrene-and phenanthrolinedione as well as benzil allowed successful preparation of the expected derivatives, while acenaphthene-quinone, naphthoquinone or 3,5-di-tert-butyl-o-quinone demonstrated low stability under reaction conditions and thus low conversion of the formylporphyrin precursor. The obtained compounds were isolated in pure form and characterized with a set of physicochemical methods. The successful demetalation of the representatives of the synthesized family of derivatives opens further access to a variety of metal complexes.

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confidence: 99%

Efficient Approach to Functionalized β-Imidazolylporphyrins

Polivanovskaia,

Shremzer,

Voronova

et al. 2023

MHC

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Stationary concentration of 1O2 over 1O2 quantum yield: Next level of photoactivity analysis

Korobkov,

Birin,

Tsivadze

2023

Dyes and Pigments

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DFT Evaluation of Reactivity of β-Substituted meso-Bromoporphyrins towards Nucleophilic Substitution

Cited by 2 publications

References 27 publications

Efficient Approach to Functionalized β-Imidazolylporphyrins

Efficient Approach to Functionalized β-Imidazolylporphyrins

Stationary concentration of 1O2 over 1O2 quantum yield: Next level of photoactivity analysis

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