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 S0 → S1v 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.
| Original language | English |
|---|---|
| Pages (from-to) | 4175-4187 |
| Number of pages | 13 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2017 |
| Issue number | 28 |
| DOIs | |
| Publication status | Published - 1 Jan 2017 |
| Externally published | Yes |
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Keywords
- Density functional calculations
- Fluorescence
- Functional organic materials
- Heterocycles
- Hydrogen bonds
- Solvatochromism
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Synthesis of Thiazoles Bearing Aryl Enamine/Aza-enamine Side Chains : Effect of the π-Conjugated Spacer Structure and Hydrogen Bonding on Photophysical Properties. / Lugovik, Kseniya I.; Popova, Aleksandra V.; Eltyshev, Alexander K.; Benassi, Enrico; Belskaya, Nataliya P.
In: European Journal of Organic Chemistry, Vol. 2017, No. 28, 01.01.2017, p. 4175-4187.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of Thiazoles Bearing Aryl Enamine/Aza-enamine Side Chains
T2 - Effect of the π-Conjugated Spacer Structure and Hydrogen Bonding on Photophysical Properties
AU - Lugovik, Kseniya I.
AU - Popova, Aleksandra V.
AU - Eltyshev, Alexander K.
AU - Benassi, Enrico
AU - Belskaya, Nataliya P.
PY - 2017/1/1
Y1 - 2017/1/1
N2 - 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 S0 → S1v 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.
AB - 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 S0 → S1v 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.
KW - Density functional calculations
KW - Fluorescence
KW - Functional organic materials
KW - Heterocycles
KW - Hydrogen bonds
KW - Solvatochromism
UR - http://www.scopus.com/inward/record.url?scp=85026658221&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85026658221&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201700518
DO - 10.1002/ejoc.201700518
M3 - Article
VL - 2017
SP - 4175
EP - 4187
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 28
ER -