Synthesis of 5-Acyl-2-Amino-3-Cyanothiophenes: Chemistry and Fluorescent Properties

Kseniya I. Lugovik, Alexander K. Eltyshev, Enrico Benassi, Nataliya P. Belskaya

Результат исследований: Материалы для журналаСтатья

5 Цитирования (Scopus)

Выдержка

Independent of the substrate structure and reaction conditions, 3-amino-2-cyanothioacrylamides, which contain two active electrophilic centers, were shown to interact with various active halo methylene compounds under mild conditions to afford 5-acyl-2-amino-3-cyanothiophenes as the only products. A series of new polyfunctional thiophene derivatives with a rare combination of functionalities were synthesized, and their photophysical properties were experimentally and computationally investigated. The calculated electronic characteristics of the ground and excited states were compared to the experimental results, which provided a good understanding of the relationship between the optoelectronic properties and the molecular structures. After absorption of light quanta, the systems populate an intramolecular charge-transfer (ICT) Franck–Condon state, and emission occurs from a twisted ICT minimum.

Язык оригиналаАнглийский
Страницы (с-по)2410-2425
Число страниц16
ЖурналChemistry - An Asian Journal
Том12
Номер выпуска18
DOI
СостояниеОпубликовано - 19 сен 2017
Опубликовано для внешнего пользованияДа

Отпечаток

Thiophenes
Molecular Structure
Charge transfer
Light
Excited states
Optoelectronic devices
Ground state
Molecular structure
Derivatives
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Цитировать

Synthesis of 5-Acyl-2-Amino-3-Cyanothiophenes : Chemistry and Fluorescent Properties. / Lugovik, Kseniya I.; Eltyshev, Alexander K.; Benassi, Enrico; Belskaya, Nataliya P.

В: Chemistry - An Asian Journal, Том 12, № 18, 19.09.2017, стр. 2410-2425.

Результат исследований: Материалы для журналаСтатья

Lugovik, Kseniya I. ; Eltyshev, Alexander K. ; Benassi, Enrico ; Belskaya, Nataliya P. / Synthesis of 5-Acyl-2-Amino-3-Cyanothiophenes : Chemistry and Fluorescent Properties. В: Chemistry - An Asian Journal. 2017 ; Том 12, № 18. стр. 2410-2425.
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T2 - Chemistry and Fluorescent Properties

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AU - Eltyshev, Alexander K.

AU - Benassi, Enrico

AU - Belskaya, Nataliya P.

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AB - Independent of the substrate structure and reaction conditions, 3-amino-2-cyanothioacrylamides, which contain two active electrophilic centers, were shown to interact with various active halo methylene compounds under mild conditions to afford 5-acyl-2-amino-3-cyanothiophenes as the only products. A series of new polyfunctional thiophene derivatives with a rare combination of functionalities were synthesized, and their photophysical properties were experimentally and computationally investigated. The calculated electronic characteristics of the ground and excited states were compared to the experimental results, which provided a good understanding of the relationship between the optoelectronic properties and the molecular structures. After absorption of light quanta, the systems populate an intramolecular charge-transfer (ICT) Franck–Condon state, and emission occurs from a twisted ICT minimum.

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