Structure-fluorescence relationships in 2-ary1-5-(2 '-aminophenyl)-4-hydroxy-1,3-thiazoles

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F19%3A39914399" target="_blank" >RIV/00216275:25310/19:39914399 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0022286018309578?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0022286018309578?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.molstruc.2018.08.017" target="_blank" >10.1016/j.molstruc.2018.08.017</a>

Result language
angličtina
Original language name
Structure-fluorescence relationships in 2-ary1-5-(2 '-aminophenyl)-4-hydroxy-1,3-thiazoles
Original language description
Five substituted 2-aryl-4-hydroxy-5-(2'-aminophenyl)-1,3-thiazoles have been studied for their fluorescence properties under neutral and alkaline conditions in solutions of various organic solvents. From comparison with the analogous 2-aryl-4-hydroxy-5-(2'-hydroxyphenyl)-1,3-thiazoles it is clear that both in neutral as well as in the deprotonated state the presence of the 2'-amino group lowers the fluorescence quantum yields (Phi). Introduction of an electron withdrawing groups into the 2-aryl group further decreases Phi. Upon deprotonation of the 4-hydroxy group a large bathochromic shift of the absorption (Delta lambda(A)=100-125 nm) as well as emission (Delta lambda(F)=100-120 nm) bands occurs. An intramolecular hydrogen bond between the amino and hydroxyl groups is obvious. The first absorption band of all studied compounds corresponds to a pi-pi* HOMO-LUMO transition with a CT character. Thiazoles 3b-f and their deprotonated forms 3b(-)-f(-) display fluorescence properties with large Stokes shift (ca 9000 cm(-1) and 6000 cm(-1), respectively) and moderate quantum yields (0.11-0.41), both are connected with the presence of inter and intramolecular hydrogen bonds.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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