Synthesis of Thiazoles Bearing Aryl Enamine/Aza-enamine Side Chains: Effect of the pi-Conjugated Spacer Structure and Hydrogen Bonding on Photophysical Properties / Lugovik Kseniya I.,Popova Aleksandra V.,Eltyshev Alexander K.,Benassi Enrico,Belskaya Nataliya P. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2017. - V. , l. 28. - P. 4175-4187.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

An efficient synthesis of a new series of di- and trisubstituted thiazoles (TZs) bearing aryl enamine side-chains (ETZs) has been developed and the optical properties of these compounds compared with structural analogues containing the isoelectronic aza-enamine group (ATZs). Spectral characterization demonstrated the difference in the absorption and fluorescence of the ETZs and ATZs in solution and the emergence of fluorescent ETZs in the solid state. The optimized structural geometries and weak intramolecular interactions, electronic characteristics of the ground and excited states, HOMO and LUMO analyses, changes in electron density after S-0 S-1v excitation and maps of electrostatic potential (MEPs) calculated by means of DFT have allowed us to estimate the particularities of the geometric and electronic structures of the ETZs and ATZs in the ground and excited states. The availability, synthetic simplicity, stability, large Stokes shifts and high sensitivity to the microenvironment (fluorosolvatochromic behaviour) make the obtained TZs a useful platform for the further design and synthesis of new effective compounds for applications in the field of fluorescence imaging.

Author keywords:

Functional organic materials; Heterocycles; Fluorescence; Solvatochromism; Hydrogen bonds; Density functional calculations PEPTIDE NUCLEIC-ACIDS; EXCITED-STATE; TD-DFT; FLUORESCENT; CHROMOPHORES; BASE; STRATEGY; SOLVENT; ORANGE; PROBES

DOI:

10.1002/ejoc.201700518

Web of Science ID:

ISI:000407038200013

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	AUG 2
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	PEPTIDE NUCLEIC-ACIDS; EXCITED-STATE; TD-DFT; FLUORESCENT; CHROMOPHORES; BASE; STRATEGY; SOLVENT; ORANGE; PROBES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
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 {[}02.A03.21.0006]; Russian Foundation for Basic Research (RFBR) {[}16-33-00327 mol\_a]; Italian ``Ministero per l{''}Universita e la Ricerca Scientifica e Tecnologica{''} {[}RBFR13PSB6]
Funding-Text	This research was supported by the Government of the Russian Federation (Act 211, contract \# 02.A03.21.0006). K. L. thanks the Russian Foundation for Basic Research (RFBR) for funding (No 16-33-00327 mol\_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	45
Usage-Count-Last-180-days	6
Usage-Count-Since-2013	6
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	FC7RA