Design and synthesis of disubstituted and trisubstituted thiazoles as multifunctional fluorophores with large Stokes shifts

Polina O. Suntsova, Alexander K. Eltyshev, Tatiana A. Pospelova, Pavel A. Slepukhin, Enrico Benassi, Nataliya P. Belskaya

Research output: Contribution to journalArticle

Abstract

A series of fluorophores based on a thiazole core have been synthesized and shown to be very sensitive to both structural changes and the microenvironment. Simple modifications of the substituents’ electronic nature, spatial effects and location in the molecule allow the tuning of the photophysical properties of the investigated compounds and their susceptibility to the environment via the exhibition of long-wavelength emission, large Stokes shifts and good quantum yields. Additionally, the thiazole-2-acrylonitrile fluorophores demonstrate a multifunctional character with significant fluorescence properties (i.e., quantum yields and a large Stokes shift in both the liquid and solid states). The influences of different factors, including the solvent polarity, on the fluorescence properties of the synthesized compounds are discussed in detail. Quantum mechanical methods are employed to understand the underlying transitions and explain the experimental results. This work provides further information for the design of new sensors that have large Stokes shifts.

Original languageEnglish
Pages (from-to)60-71
Number of pages12
JournalDyes and Pigments
Volume166
DOIs
Publication statusPublished - 1 Jul 2019

Fingerprint

Thiazoles
Fluorophores
Quantum yield
Fluorescence
Acrylonitrile
Tuning
Wavelength
Molecules
Sensors
Liquids

Keywords

  • Arylidene
  • Biosensor
  • Fluorescence
  • Solvatochromism
  • Stokes shift
  • Thiazole

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

Design and synthesis of disubstituted and trisubstituted thiazoles as multifunctional fluorophores with large Stokes shifts. / Suntsova, Polina O.; Eltyshev, Alexander K.; Pospelova, Tatiana A.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.

In: Dyes and Pigments, Vol. 166, 01.07.2019, p. 60-71.

Research output: Contribution to journalArticle

Suntsova, Polina O. ; Eltyshev, Alexander K. ; Pospelova, Tatiana A. ; Slepukhin, Pavel A. ; Benassi, Enrico ; Belskaya, Nataliya P. / Design and synthesis of disubstituted and trisubstituted thiazoles as multifunctional fluorophores with large Stokes shifts. In: Dyes and Pigments. 2019 ; Vol. 166. pp. 60-71.
@article{a3e47c7e34ea4431a621dd461f50c1be,
title = "Design and synthesis of disubstituted and trisubstituted thiazoles as multifunctional fluorophores with large Stokes shifts",
abstract = "A series of fluorophores based on a thiazole core have been synthesized and shown to be very sensitive to both structural changes and the microenvironment. Simple modifications of the substituents’ electronic nature, spatial effects and location in the molecule allow the tuning of the photophysical properties of the investigated compounds and their susceptibility to the environment via the exhibition of long-wavelength emission, large Stokes shifts and good quantum yields. Additionally, the thiazole-2-acrylonitrile fluorophores demonstrate a multifunctional character with significant fluorescence properties (i.e., quantum yields and a large Stokes shift in both the liquid and solid states). The influences of different factors, including the solvent polarity, on the fluorescence properties of the synthesized compounds are discussed in detail. Quantum mechanical methods are employed to understand the underlying transitions and explain the experimental results. This work provides further information for the design of new sensors that have large Stokes shifts.",
keywords = "Arylidene, Biosensor, Fluorescence, Solvatochromism, Stokes shift, Thiazole",
author = "Suntsova, {Polina O.} and Eltyshev, {Alexander K.} and Pospelova, {Tatiana A.} and Slepukhin, {Pavel A.} and Enrico Benassi and Belskaya, {Nataliya P.}",
year = "2019",
month = "7",
day = "1",
doi = "10.1016/j.dyepig.2019.02.051",
language = "English",
volume = "166",
pages = "60--71",
journal = "Dyes and Pigments",
issn = "0143-7208",
publisher = "Elsevier BV",

}

TY - JOUR

T1 - Design and synthesis of disubstituted and trisubstituted thiazoles as multifunctional fluorophores with large Stokes shifts

AU - Suntsova, Polina O.

AU - Eltyshev, Alexander K.

AU - Pospelova, Tatiana A.

AU - Slepukhin, Pavel A.

AU - Benassi, Enrico

AU - Belskaya, Nataliya P.

PY - 2019/7/1

Y1 - 2019/7/1

N2 - A series of fluorophores based on a thiazole core have been synthesized and shown to be very sensitive to both structural changes and the microenvironment. Simple modifications of the substituents’ electronic nature, spatial effects and location in the molecule allow the tuning of the photophysical properties of the investigated compounds and their susceptibility to the environment via the exhibition of long-wavelength emission, large Stokes shifts and good quantum yields. Additionally, the thiazole-2-acrylonitrile fluorophores demonstrate a multifunctional character with significant fluorescence properties (i.e., quantum yields and a large Stokes shift in both the liquid and solid states). The influences of different factors, including the solvent polarity, on the fluorescence properties of the synthesized compounds are discussed in detail. Quantum mechanical methods are employed to understand the underlying transitions and explain the experimental results. This work provides further information for the design of new sensors that have large Stokes shifts.

AB - A series of fluorophores based on a thiazole core have been synthesized and shown to be very sensitive to both structural changes and the microenvironment. Simple modifications of the substituents’ electronic nature, spatial effects and location in the molecule allow the tuning of the photophysical properties of the investigated compounds and their susceptibility to the environment via the exhibition of long-wavelength emission, large Stokes shifts and good quantum yields. Additionally, the thiazole-2-acrylonitrile fluorophores demonstrate a multifunctional character with significant fluorescence properties (i.e., quantum yields and a large Stokes shift in both the liquid and solid states). The influences of different factors, including the solvent polarity, on the fluorescence properties of the synthesized compounds are discussed in detail. Quantum mechanical methods are employed to understand the underlying transitions and explain the experimental results. This work provides further information for the design of new sensors that have large Stokes shifts.

KW - Arylidene

KW - Biosensor

KW - Fluorescence

KW - Solvatochromism

KW - Stokes shift

KW - Thiazole

UR - http://www.scopus.com/inward/record.url?scp=85062923824&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85062923824&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2019.02.051

DO - 10.1016/j.dyepig.2019.02.051

M3 - Article

VL - 166

SP - 60

EP - 71

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

ER -