The effect of annulation of benzene rings on the photophysics and electronic structure of tetraazachlorin molecules

Першукевич, П. П.; Volkovich, D. I.; Гладков, Л. Л.; Dudkin, Semyon V.; Kuzmitsky, V. A.; Макарова, Е. А.; Solovyev, K. N.

doi:10.1134/s0030400x17100198

Cited by 6 publications

(6 citation statements)

References 40 publications

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“…A high-yield reaction occurred when indole reacted with alkylating agents in the presence of sodium hydride in DMF (Scheme 5). Annulation of a benzene ring to a fluorophore system is known to improve its photophysical characteristics [25][26][27]. Therefore, we performed aromatization of the cyclohexene moiety to a benzene fragment in compound 8g (Scheme 6).…”

Section: Synthesis Of Pyrano[23-e]indolesmentioning

confidence: 99%

Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles

et al. 2022

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This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-f]indole, pyrano[2,3-g]indole, pyrano[2,3-f]indole, and pyrano[2,3-e]indole and photophysical studies in this series. The synthesis of pyrano[3,2-f], [2,3-g], and [2,3-e]indoles involve a tandem of Bischler–Möhlau reaction of 3-aminophenol with benzoin to form 6-hydroxy- or 4-hydroxyindole followed by Pechmann condensation of these hydroxyindoles with β-ketoesters. Pyrano[2,3-f]indoles were synthesized through the Nenitzescu reaction of p-benzoquinone and ethyl aminocrotonates and subsequent Pechmann condensation of the obtained 5-hydroxyindole derivatives. Among the pyranoindoles studied, the most promising were pyrano[3,2-f] and [2,3-g]indoles. These compounds were characterized by moderate to high quantum yields (30–89%) and a large (9000–15,000 cm−1) Stokes shift. More detailed photophysical studies were carried out for a series of the most promising derivatives of pyrano[3,2-f] and [2,3-g]indoles to demonstrate their positive solvatochromism, and the data collected was analyzed using Lippert-Mataga equation. Quantum chemical calculations were performed to deepen the knowledge of the absorption and emission properties of pyrano[3,2-f] and [2,3-g]indoles as well as to explain their unusual geometries and electronic structures.

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Section: Synthesis Of Pyrano[23-e]indolesmentioning

confidence: 99%

Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles

et al. 2022

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“…Спектры поглощения всех трех исследованных комплексов Pt представлены в работе [8] в виде рисунков (в МТГФ, толуоле и ДМСО) и в виде численных данных (λ max , lg ε) -в хлорбензоле и гексане. В [8] приведены также данные для комплексов Pd в хлорбензоле, а в работе [6] -для Zn1 в толуоле; спектры поглощения последнего комплекса в ДМСО даны там в рисунках. Эта информация позволяет оценить влияние на абсорбционные спектры растворителя и природы металла.…”

Section: экспериментальные результатыunclassified

“…В области аналога полосы Соре у комплексов гидропорфиразинов регистрируется диффузная полоса с двумя максимумами. Для Zn1 измерения поляризации флуоресценции выявили частичную поляризацию этих близких полос по осям x и y, но различия в значениях степени поляризации невелики [6]. Это интерпретировано как проявление здесь нескольких электронных переходов с различной поляризацией.…”

Section: экспериментальные результатыunclassified

“…Это интерпретировано как проявление здесь нескольких электронных переходов с различной поляризацией. Квантово-химический расчет молекулы Mg1 также выявил в этой области несколько электронных переходов [6].…”

Section: экспериментальные результатыunclassified

“…Ареногидропорфиразины [1][2][3][4] и их производные [5] -новый подкласс тетрапиррольных соединений с интенсивным поглощением в ближнем ИК диапазоне (БИК, NIR). Спектрально-люминесцентные свойства бензогидропорфиразинов -цинковых комплексов [6] и соответствующих свободных оснований [6,7] -исследовались нашей научной группой. В работе [8] была зарегистрирована БИК-фосфоресценция комплексов палладия и платины с тетраметилтрибензодигидропорфиразином и октаметилдибензотетрагидропорфиразином с соседним расположением гидрированных пиррольных колец.…”

Section: Introductionunclassified

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Люминесценция Pd и Pt бензогидропорфиразинов в ближнем ИК диапазоне

Першукевич¹,

Volkovich²,

Макарова³

et al. 2020

Журнал Технической Физики

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Phosphorescence in the near-IR range under stationary lamp excitation was studied of three palladium and three platinum complexes of benzocondensed hydroporphyrazine phthalocyanine analogues in which molecule one or two isoindole fragments are replaced by a hydrogenated pyrrole ring, giving macrocycles of photosynthetic pigments analogues of chlorin, bacteriochlorin and isobacteriochlorin types. For the first time, the phosphorescence spectra of trans-dibenzotetrahydroporphyrazines (for both platinum and palladium) have been registered, which detection failed during long time due to the record removal of 0-0 bands from the visible area (1.67 and 1.52 µm for Pd and Pt), and also because of the small quantum yield of phosphorescence. The fluorescence of these complexes was also detected.in the near-IR range. On the basis of comparison of experimental results with own and literature data for palladium complexes of a number of tetrapyrroles is shown the approximate additivity of the influence of structural factors — hydrogenation of pyrrole rings, aza- and benzo substitution — on the energy of the lower triplet state T1. The information obtained is essential for targeted creation of emitters in the near-IR range (1.0-1.7 µm).

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Quantum-Chemical Calculations of the Geometric Structures and Electronic Spectra of Phthalocyanines MgPc and H2Pc and Their β-Octaphenyl Derivatives

et al. 2018

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The effect of annulation of benzene rings on the photophysics and electronic structure of tetraazachlorin molecules

Cited by 6 publications

References 40 publications

Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles

Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles

Люминесценция Pd и Pt бензогидропорфиразинов в ближнем ИК диапазоне

Quantum-Chemical Calculations of the Geometric Structures and Electronic Spectra of Phthalocyanines MgPc and H2Pc and Their β-Octaphenyl Derivatives

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