Novel 5-Aryl-[1,2,4]triazoloquinazoline Fluorophores

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Novel 5-Aryl-[1,2,4]triazoloquinazoline Fluorophores : Synthesis, Comparative Studies of the Optical Properties and ICT-Based Sensing Application. / Kopotilova, Alexandra E.; Permyakova, Julia V.; Starnovskaya, Ekaterina S.; Moshkina, Tatyana N.; Novikov, Alexander S.; Slepukhin, Pavel A.; Nosova, Emiliya V.

In: Molecules, Vol. 30, No. 22, 4420, 15.11.2025.

Research output: Contribution to journal › Article › peer-review

Author

Kopotilova, Alexandra E. ; Permyakova, Julia V. ; Starnovskaya, Ekaterina S. ; Moshkina, Tatyana N. ; Novikov, Alexander S. ; Slepukhin, Pavel A. ; Nosova, Emiliya V. / Novel 5-Aryl-[1,2,4]triazoloquinazoline Fluorophores : Synthesis, Comparative Studies of the Optical Properties and ICT-Based Sensing Application. In: Molecules. 2025 ; Vol. 30, No. 22.

BibTeX

@article{43aae52a65564b2fab19b4ceaf16ca87,

title = "Novel 5-Aryl-[1,2,4]triazoloquinazoline Fluorophores: Synthesis, Comparative Studies of the Optical Properties and ICT-Based Sensing Application",

abstract = "Novel tricyclic fluorophores were obtained from 2-aryl-[1,2,4]triazolo[1,5-c]quinazoline-5(6H)-ones through chlorodesoxygenation and subsequent Suzuki–Imamura cross-coupling reactions. Their π-extended analogues were synthesized from 5-(4-bromophenyl)-[1,2,4]triazoloquinazolines. The structure of target fluorophores was confirmed by X-ray single crystal diffraction. Photophysical properties in solutions and solid state were studied. 5-Aminoaryl-substituted [1,2,4]triazolo[1,5-c]quinazolines revealed bright blue fluorescence in toluene (ΦF > 95%), which can be tuned by solvent polarity, the electronic nature and rigidity of the donor fragment, the π-spacer length, and the annelation pattern. Intramolecular charge transfer (ICT) behaviour was demonstrated using both experimental and theoretical data. Distinct acid-induced spectral and fluorescence changes upon protonation were observed for diethylamino-containing derivatives, indicating their potential applicability as dual-mode (polarity and pH) molecular sensors.",

keywords = "nitrogen heterocycles, luminescence, push-pull quinazolines, two-photon absorption, electronic-structure calculations, electronic-structure calculations, luminescence, nitrogen heterocycles, push-pull quinazolines, two-photon absorption",

author = "Kopotilova, {Alexandra E.} and Permyakova, {Julia V.} and Starnovskaya, {Ekaterina S.} and Moshkina, {Tatyana N.} and Novikov, {Alexander S.} and Slepukhin, {Pavel A.} and Nosova, {Emiliya V.}",

year = "2025",

month = nov,

day = "15",

doi = "10.3390/molecules30224420",

language = "English",

volume = "30",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "22",

}

RIS

TY - JOUR

T1 - Novel 5-Aryl-[1,2,4]triazoloquinazoline Fluorophores

T2 - Synthesis, Comparative Studies of the Optical Properties and ICT-Based Sensing Application

AU - Kopotilova, Alexandra E.

AU - Permyakova, Julia V.

AU - Starnovskaya, Ekaterina S.

AU - Moshkina, Tatyana N.

AU - Novikov, Alexander S.

AU - Slepukhin, Pavel A.

AU - Nosova, Emiliya V.

PY - 2025/11/15

Y1 - 2025/11/15

N2 - Novel tricyclic fluorophores were obtained from 2-aryl-[1,2,4]triazolo[1,5-c]quinazoline-5(6H)-ones through chlorodesoxygenation and subsequent Suzuki–Imamura cross-coupling reactions. Their π-extended analogues were synthesized from 5-(4-bromophenyl)-[1,2,4]triazoloquinazolines. The structure of target fluorophores was confirmed by X-ray single crystal diffraction. Photophysical properties in solutions and solid state were studied. 5-Aminoaryl-substituted [1,2,4]triazolo[1,5-c]quinazolines revealed bright blue fluorescence in toluene (ΦF > 95%), which can be tuned by solvent polarity, the electronic nature and rigidity of the donor fragment, the π-spacer length, and the annelation pattern. Intramolecular charge transfer (ICT) behaviour was demonstrated using both experimental and theoretical data. Distinct acid-induced spectral and fluorescence changes upon protonation were observed for diethylamino-containing derivatives, indicating their potential applicability as dual-mode (polarity and pH) molecular sensors.

AB - Novel tricyclic fluorophores were obtained from 2-aryl-[1,2,4]triazolo[1,5-c]quinazoline-5(6H)-ones through chlorodesoxygenation and subsequent Suzuki–Imamura cross-coupling reactions. Their π-extended analogues were synthesized from 5-(4-bromophenyl)-[1,2,4]triazoloquinazolines. The structure of target fluorophores was confirmed by X-ray single crystal diffraction. Photophysical properties in solutions and solid state were studied. 5-Aminoaryl-substituted [1,2,4]triazolo[1,5-c]quinazolines revealed bright blue fluorescence in toluene (ΦF > 95%), which can be tuned by solvent polarity, the electronic nature and rigidity of the donor fragment, the π-spacer length, and the annelation pattern. Intramolecular charge transfer (ICT) behaviour was demonstrated using both experimental and theoretical data. Distinct acid-induced spectral and fluorescence changes upon protonation were observed for diethylamino-containing derivatives, indicating their potential applicability as dual-mode (polarity and pH) molecular sensors.

KW - nitrogen heterocycles

KW - luminescence

KW - push-pull quinazolines

KW - two-photon absorption

KW - electronic-structure calculations

KW - luminescence

KW - nitrogen heterocycles

KW - push-pull quinazolines

KW - two-photon absorption

UR - https://www.mdpi.com/1420-3049/30/22/4420

UR - https://www.mendeley.com/catalogue/5ecb8ffe-b44e-36c6-b953-2138d19ba00f/

U2 - 10.3390/molecules30224420

DO - 10.3390/molecules30224420

M3 - Article

C2 - 41302477

VL - 30

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 22

M1 - 4420

ER -

ID: 144406981