TY - JOUR

T1 - (A)symmetric chromophores based on cyano and fluorine-substituted 2,3-bis(5-arylthiophen-2-yl)quinoxalines

T2 - Synthesis, photophysical properties and application prospects

AU - Moshkina, Tatyana N.

AU - Nosova, Emiliya V.

AU - Kopotilova, Alexandra E.

AU - Ośmiałowski, Borys

AU - Reguant, Alejandro I.

AU - Slepukhin, Pavel A.

AU - Lipunova, Galina N.

AU - Taniya, Olga S.

AU - Kalinichev, Alexey A.

AU - Charushin, Valery N.

N1 - Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/8

Y1 - 2022/8

N2 - A series of novel V-shaped D-π-A-π-D push-pull chromophores, containing two aminoaryl electron donors (D), 1,5-thiophenylene π-conjugated spacer and a 6-cyano- or 6,7-difluoroquinoxaline electron acceptor (A), was designed, synthesized, and characterized. 6-Cyano derivatives demonstrated red shift of absorption and emission maxima compared with 6,7-difluoro counterparts. The compounds displayed positive emission solvatochromism with increasing solvent polarity. Additionally, emission behavior of all compounds in THF/water mixture and solid state was investigated. Moreover, the two-photon excited fluorescence (2 PE) spectra of carbazolyl-containing chromophores were measured. Replacement of 6,7-difluoroquinoxaline core by 6-cyanoquinoxaline increases two-photon absorption cross section (δ2PA) value by more than 10 times. 6,7-Difluoroquinoxalines demonstrated changes in emission maxima or/and intensity after mechanic stimulation. Electronic-structure calculations with the use of quantum-chemistry methods were performed to have a deeper insight into experimental data. In summary, the obtained results show multifunctional nature of V-shaped 2,3-bis(5-arylthiephen-2-yl)quinoxalines and their potential utility in diverse applications.

AB - A series of novel V-shaped D-π-A-π-D push-pull chromophores, containing two aminoaryl electron donors (D), 1,5-thiophenylene π-conjugated spacer and a 6-cyano- or 6,7-difluoroquinoxaline electron acceptor (A), was designed, synthesized, and characterized. 6-Cyano derivatives demonstrated red shift of absorption and emission maxima compared with 6,7-difluoro counterparts. The compounds displayed positive emission solvatochromism with increasing solvent polarity. Additionally, emission behavior of all compounds in THF/water mixture and solid state was investigated. Moreover, the two-photon excited fluorescence (2 PE) spectra of carbazolyl-containing chromophores were measured. Replacement of 6,7-difluoroquinoxaline core by 6-cyanoquinoxaline increases two-photon absorption cross section (δ2PA) value by more than 10 times. 6,7-Difluoroquinoxalines demonstrated changes in emission maxima or/and intensity after mechanic stimulation. Electronic-structure calculations with the use of quantum-chemistry methods were performed to have a deeper insight into experimental data. In summary, the obtained results show multifunctional nature of V-shaped 2,3-bis(5-arylthiephen-2-yl)quinoxalines and their potential utility in diverse applications.

KW - Aggregation induced emission enhancement

KW - Mechanochromic properties

KW - Push-pull chromophore

KW - Quinoxaline

KW - Two-photon absorption

UR - http://www.scopus.com/inward/record.url?scp=85130618423&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/0b74da11-8588-327f-9cd3-180410399579/

U2 - 10.1016/j.dyepig.2022.110434

DO - 10.1016/j.dyepig.2022.110434

M3 - Article

AN - SCOPUS:85130618423

VL - 204

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 110434

ER -