Fluorinated derivatives of 2-azinyl-4-(4-aminophenyl)quinazolines: Synthesis and photophysical properties

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Fluorinated derivatives of 2-azinyl-4-(4-aminophenyl)quinazolines: Synthesis and photophysical properties. / Kopotilova, Alexandra ; Valieva, Maria ; Starnovskaya, Ekaterina et al.
In: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 448, 115350, 01.02.2024.

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

BibTeX

@article{32a9d29f1bfb48bf8a9caa42bbdb23b0,

title = "Fluorinated derivatives of 2-azinyl-4-(4-aminophenyl)quinazolines: Synthesis and photophysical properties",

abstract = "Herein, we present design, synthesis and photophysical properties of fluorinated 2-pyridyl and 2-pyrimidinylquinazolines bearing electron donating aminoaryl moiety at the position 4. The described compounds are synthesized in three steps starting from 2-cyanoazine and fluorinated anthranilic acid. The structures of the target compounds are confirmed by NMR spectroscopy, mass spectrometry as well as X-ray diffraction analysis. The photophysical characteristics are investigated in toluene and MeCN. In case of Et2N- and Ph2N-derivatives the quantum yields increase when going from MeCN to toluene and reach 87 %, whereas emission intensity of carbazolyl counterparts reduces with the decrease in solvent polarity. All the compounds exhibit considerable sensitivity to solvent polarity and change their emission color from blue to red–orange. Additionally, the 2,4-disubstituted fluorophores display two-photon absorption in MeCN with δ2PA in the range of 18.9–227.8 GM.",

author = "Alexandra Kopotilova and Maria Valieva and Ekaterina Starnovskaya and Tatyana Moshkina and Emiliya Nosova and Olga Taniya and Alexey Kalinichev and Dmitry Kopchuk and Pavel Slepukhin and Vasiliy Gaviko and Grigory Kim and Valery Charushin",

note = "The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program) is gratefully acknowledged. Theoretical calculations were performed using «Uran» supercomputer of IMM UB RAS.",

year = "2024",

month = feb,

day = "1",

doi = "10.1016/j.jphotochem.2023.115350",

language = "English",

volume = "448",

journal = "Journal of Photochemistry and Photobiology A: Chemistry",

issn = "1010-6030",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Fluorinated derivatives of 2-azinyl-4-(4-aminophenyl)quinazolines: Synthesis and photophysical properties

AU - Kopotilova, Alexandra

AU - Valieva, Maria

AU - Starnovskaya, Ekaterina

AU - Moshkina, Tatyana

AU - Nosova, Emiliya

AU - Taniya, Olga

AU - Kalinichev, Alexey

AU - Kopchuk, Dmitry

AU - Slepukhin, Pavel

AU - Gaviko, Vasiliy

AU - Kim, Grigory

AU - Charushin, Valery

N1 - The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program) is gratefully acknowledged. Theoretical calculations were performed using «Uran» supercomputer of IMM UB RAS.

PY - 2024/2/1

Y1 - 2024/2/1

N2 - Herein, we present design, synthesis and photophysical properties of fluorinated 2-pyridyl and 2-pyrimidinylquinazolines bearing electron donating aminoaryl moiety at the position 4. The described compounds are synthesized in three steps starting from 2-cyanoazine and fluorinated anthranilic acid. The structures of the target compounds are confirmed by NMR spectroscopy, mass spectrometry as well as X-ray diffraction analysis. The photophysical characteristics are investigated in toluene and MeCN. In case of Et2N- and Ph2N-derivatives the quantum yields increase when going from MeCN to toluene and reach 87 %, whereas emission intensity of carbazolyl counterparts reduces with the decrease in solvent polarity. All the compounds exhibit considerable sensitivity to solvent polarity and change their emission color from blue to red–orange. Additionally, the 2,4-disubstituted fluorophores display two-photon absorption in MeCN with δ2PA in the range of 18.9–227.8 GM.

AB - Herein, we present design, synthesis and photophysical properties of fluorinated 2-pyridyl and 2-pyrimidinylquinazolines bearing electron donating aminoaryl moiety at the position 4. The described compounds are synthesized in three steps starting from 2-cyanoazine and fluorinated anthranilic acid. The structures of the target compounds are confirmed by NMR spectroscopy, mass spectrometry as well as X-ray diffraction analysis. The photophysical characteristics are investigated in toluene and MeCN. In case of Et2N- and Ph2N-derivatives the quantum yields increase when going from MeCN to toluene and reach 87 %, whereas emission intensity of carbazolyl counterparts reduces with the decrease in solvent polarity. All the compounds exhibit considerable sensitivity to solvent polarity and change their emission color from blue to red–orange. Additionally, the 2,4-disubstituted fluorophores display two-photon absorption in MeCN with δ2PA in the range of 18.9–227.8 GM.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85178274156

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001164195200001

U2 - 10.1016/j.jphotochem.2023.115350

DO - 10.1016/j.jphotochem.2023.115350

M3 - Article

VL - 448

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

SN - 1010-6030

M1 - 115350

ER -

ID: 49258286