2-Aryl-5-amino-1,2,3-triazoles: New effective blue-emitting fluorophores / Gavlik Kseniya D.,Sukhorukova Ekaterina S.,Shafran Yuri M.,Slepukhin Pavel A.,Benassi Enrico,Belskaya Nataliya P. // DYES AND PIGMENTS. - 2017. - V. 136, l. . - P. 229-242.

ISSN/EISSN:

0143-7208 / 1873-3743

Type:

Article

Abstract:

The synthesis of a new series of 2-aryl-5-amino-1,2,3-triazole derivatives is reported. The photochemical properties of these new fluorophores were studied both experimentally and using theoretical models. The compounds were found to be fluorescent, with Stokes shifts ranging from 40 nm (2494 CM-1) to 140 nm (9461 cm(-1)) and quantum yield values between 0.004 and 0.996. The fluorescence of the 1,2,3-triazoles was highly structure dependent and could be tuned by variation of the substituents at the C-4 and C-5 atoms of triazole ring and by the electronic and spatial effect of substituents within the aromatic cycle. Photophysical studies showed moderate changes in the fluorescence quantum yields depending on the solvent polarity. The UV-Vis spectra calculations employing the time-dependent density functional theory (TD-DFT) are in good agreement with the experimental data. The favourable photophysical properties of the studied compounds and their facile and high-yielding synthesis make them excellent candidates for commercial application as fluorescent tags. (C) 2016 Elsevier Ltd. All rights reserved.

Author keywords:

2-Aryl-5-amino-1,2,3-triazole; Fluorescence; Stokes shift; Quantum yield; Solvatochromism PHOTOPHYSICAL PROPERTIES; WAVE-FUNCTIONS; BASIS-SETS; FLUORESCENCE; N-2-ARYL-1,2,3-TRIAZOLES; THERMOCHEMISTRY; EXCHANGE; DFT

DOI:

10.1016/j.dyepig.2016.08.015

Web of Science ID:

ISI:000387837200029

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JAN
Publisher	ELSEVIER SCI LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, OXON, ENGLAND
Language	English
EISSN	1873-3743
Keywords-Plus	PHOTOPHYSICAL PROPERTIES; WAVE-FUNCTIONS; BASIS-SETS; FLUORESCENCE; N-2-ARYL-1,2,3-TRIAZOLES; THERMOCHEMISTRY; EXCHANGE; DFT
Research-Areas	Chemistry; Engineering; Materials Science
Web-of-Science-Categories	Chemistry, Applied; Engineering, Chemical; Materials Science, Textiles
Author-Email	n.p.belskaya@urfu.ru
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916
Funding-Acknowledgement	Government of the Russian Federation {[}02.A03.21.0006]; Italian ``Ministero per l'Universita e la Ricerca Scientifica e Tecnologica{''} {[}FIRB] {[}RBFR13PSB6]
Funding-Text	The research was supported by the Government of the Russian Federation (Act 211, contract \# 02.A03.21.0006). E. B. thanks the Italian ``Ministero per l'Universita e la Ricerca Scientifica e Tecnologica{''} for fundings {[}FIRB 2013, RBFR13PSB6].
Number-of-Cited-References	36
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	16
Journal-ISO	Dyes Pigment.
Doc-Delivery-Number	EC1AZ