Synthesis and photophysical study of novel 3-triazinyl- and 3-pyridinyl-substituted coumarins

• Published in: Optical materials 2025-01, Vol.158, p.116471, Article 116471
• Main Authors: Potapova, Anastasia P., Taniya, Olga S., Valieva, Maria I., Khalymbadzha, Igor A., Sharapov, Ainur D., Starnovskaya, Ekaterina S., Kopchuk, Dmitry S., Gaviko, Vasiliy S., Novikov, Alexander S., Kalinichev, Alexey A., Fatykhov, Ramil F.
• Format: Article
• Language: English
• Subjects: Coumarin; DFT; NLO; Pyridine; Triazine; Two-photon absorption
• ISSN: 0925-3467
• DOI: 10.1016/j.optmat.2024.116471

A series of 3-triazinyl- and 3-pyridinyl-coumarin dyes were designed, synthesized and studied in terms of linear and nonlinear optical properties as well as charge transfer. The triazine- and pyridine-containing fluorophores were emitted green and blue light in the visible region of the spectrum, respectively, with high quantum yields. Two-photon fluorescence properties were measurement and 4b showed high two-photon absorption cross-section value (δ2PA = 285.5 GM). The dyes exhibited second-order NLO properties with static hyperpolarizability β0 in the range of 43–78 × 10−30 esu. Photophysical studies supported DFT calculations showed that the push-pull fluorophores 3g-j generated photoinduced intramolecular charge transfer states. Obtained experimental and theoretical data strongly suggests that these novel coumarin dyes are promising candidates for cell imaging. •A novel 3-triazinyl- and 3-pyridyl-7-aminocoumarin fluorophores were developed.•These coumarins absorb UV- to violet light and emit in the blue to green region.•Pyridinyl-coumarins displayed two-photon absorption with δ2PA in up to 285.5 GM.