D-π-A'-π-A chromophores with quinoxaline core in the π-electron bridge and charged heterocyclic acceptor moiety: Synthesis, DFT calculations, photophysical and electro-chemical properties

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Vol. 407; p. 113042
• Main Authors: Kalinin, Alexey A., Sharipova, Sirina M., Levitskaya, Alina I., Dudkina, Yulia B., Burganov, Timur I., Fominykh, Olga D., Katsyuba, Sergey A., Budnikova, Yulia H., Balakina, Marina Yu
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-02-2021
• Subjects: Charged chromophores; Divinylquinoxalines; Energy gap; First hyperpolarizability; Solvatochromic behavior; Voltammetry; Divinylquinoxalines; Voltammetry; Charged chromophores; Energy gap; First hyperpolarizability; Solvatochromic behavior
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2020.113042

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•D-π-Aʾ-π-A chromophores with quinoxaline core and charged heterocyclic acceptor.•Significant solvatochromic shift.•Small HOMO-LUMO energy gap.•High values of the first hyperpolarizability.
Chromophores with charged heterocyclic acceptor moiety in combination with divinylquinoxaline conjugated π-bridge show a significant solvatochromic shift, small energy gap value (determined by various methods), and large values of the first hyperpolarizability estimated by DFT. A quinoxaline-based chromophore with an indolium acceptor exhibits an outstanding solvatochromic shift (0.38 eV), probably a record one for D-π-A chromophores with a dialkyl aniline donor moiety. A good correlation between the above characteristics and the calculated NBO π-charge on the aniline nitrogen atom has been found. A change in the trend by opposite one in the characteristics in the series of quinolinium /benzothiazolium/ indolium chromophores is exhibited when passing from gas to solvent.