Synthesis of 5-Acyl-2-Amino-3-Cyanothiophenes: Chemistry and Fluorescent Properties / Lugovik Kseniya I.,Eltyshev Alexander K.,Benassi Enrico,Belskaya Nataliya P. // CHEMISTRY-AN ASIAN JOURNAL. - 2017. - V. 12, l. 18. - P. 2410-2425.

ISSN/EISSN:

1861-4728 / 1861-471X

Type:

Article

Abstract:

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.

Author keywords:

charge transfer; cyclization; fluorescence; solvatochromism; sulfur heterocycles CORRELATED MOLECULAR CALCULATIONS; INTRAMOLECULAR CHARGE-TRANSFER; GAUSSIAN-BASIS SETS; DENSITY-FUNCTIONAL THEORY; ONE-POT SYNTHESIS; PHOTOPHYSICAL PROPERTIES; OPTICAL-PROPERTIES; WAVE-FUNCTIONS; SOLVENT-FREE; THIOPHENE

DOI:

10.1002/asia.201700721

Web of Science ID:

ISI:000411081300017

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	SEP 19
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1861-471X
Keywords-Plus	CORRELATED MOLECULAR CALCULATIONS; INTRAMOLECULAR CHARGE-TRANSFER; GAUSSIAN-BASIS SETS; DENSITY-FUNCTIONAL THEORY; ONE-POT SYNTHESIS; PHOTOPHYSICAL PROPERTIES; OPTICAL-PROPERTIES; WAVE-FUNCTIONS; SOLVENT-FREE; THIOPHENE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	enrico.benassi@sns.it n.p.belskaya@urfu.ru
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017 Eltyshev, Alexander/S-4896-2017
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916 Eltyshev, Alexander/0000-0002-0157-7130 Lugovik, Kseniya/0000-0001-9099-7286
Funding-Acknowledgement	Government of the Russian Federation (Act 211) {[}02.A03.21.0006]; Russian Foundation for Basic Research {[}16-33-00327mol\_a]; Italian Ministero per l'Universita e la Ricerca Scientifica e Tecnologica {[}FIRB 2013, RBFR13PSB6]
Funding-Text	The Government of the Russian Federation (Act 211, contract \#02.A03.21.0006) supported this research. K.L. thanks the Russian Foundation for Basic Research for funding No. 16-33-00327mol\_a. E.B. thanks the Italian Ministero per l'Universita e la Ricerca Scientifica e Tecnologica for fundings {[}FIRB 2013, RBFR13PSB6].
Number-of-Cited-References	79
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	2
Journal-ISO	Chem.-Asian J.
Doc-Delivery-Number	FH3WP