Synthesis and photophysical studies of novel v-shaped 2,3-bis{5-aryl-2-thienyl}(dibenzo[f,h])quinoxalines / T. N. Moshkina, E. V. Nosova, A. E. Kopotilova [et al.] // Asian journal of organic chemistry. - 2020. - Vol. 9, № 4. - P673-681 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CROSS-COUPLING -- DIBENZO[F,H]QUINOXALINE -- DONOR-ACCEPTOR-DONOR CHROMOPHORES -- FLUORESCENCE -- SENSORS Аннотация: A series of novel V-shaped luminophores containing electron-withdrawing dibenzo[f,h]quinoxaline core and arylthienyl donor fragments at positions 2 and 3 has been synthesized. The absorption spectra (UV/vis) were recorded in several solvents, whereas emission spectra were recorded in solutions and powders. The solvatochromism as well as halochromism of obtained compounds was also explored. Electronic-structure calculations using quantum-chemistry methods were performed to further analyse experimental results. All characteristics were compared with that of 2,3-bis(arylthienyl)quinoxaline counterparts. The halochromic effect studies showed that upon gradual addition of trifluoroacetic acid (TFA) to the toluene solution of diethylaminophenyl-substituted dibenzo[f,h]quinoxaline chromophore, absorption and emission changed. Observed band shifts were more distinct in the case of mentioned quinoxaline than for other derivatives. All of the (dibenzo[f,h])quinoxaline chromophores exhibited good sensitivity toward nitro-containing explosives with high Stern-Volmer constants up to 57800 M−1, these results are remarkable for such heterocyclic systems. |