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Triazole-Based Functionalized Olygo(Arylene Ethynylene)s-Synthesis and Properties
Anastasia I Govdi1, Vasiliy V Menchikov1, Ilya E Kolesnikov2
1Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.
None:
Oligo(arylene ethynylene)s (OAEs) containing 4,5-(diethynylaryl)-1,2,3-triazoles with 3(OMe) and NR2 substituents at the 5-position and bis-1,4-dialkoxybenzene moieties as spacers at the 4-position were obtained using the retro-Favorskii reaction as a key step. The most intense fluorescence was observed for OAEs with a trimethoxyphenyl substituent in THF solutions, with a quantum yield of up to 88%. Increasing the solvent polarity had minimal effect on the emission of trimethoxyphenyl substituted derivatives. A notable red shift in emission spectra was observed with increasing solvent polarity for OAEs 10a,g containing para-dimethylaminophenyl group. Their emission spectra in aqueous organic solutions revealed that an increase in water fraction in THF/water mixtures led to a bathochromic shift in emission spectra maxima accompanied by a hypochromic effect. An increase in intensity was observed in aqueous acetonitrile and DMSO. The maximum intensity was observed in DMSO solutions containing 30% water, which is attributed to aggregate-induced emission enhancement. Dynamic light scattering data also confirmed the formation of nanoscale aggregates in aqueous organic mixtures.
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