TY - JOUR

T1 - Triazole-Based Functionalized Olygo(Arylene Ethynylene)s—Synthesis and Properties

AU - Говди, Анастасия Иосифовна

AU - Менчиков, Василий Владиславович

AU - Колесников, Илья Евгеньевич

AU - Балова, Ирина Анатольевна

PY - 2025/11/22

Y1 - 2025/11/22

N2 - Oligo(arylene ethynylene)s (OAEs) containing 4,5-(diethynylaryl)-1,2,3-triazoles with 3(OMe) and NR 2 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.

AB - Oligo(arylene ethynylene)s (OAEs) containing 4,5-(diethynylaryl)-1,2,3-triazoles with 3(OMe) and NR 2 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.

UR - https://www.mendeley.com/catalogue/6abf51e3-fe3a-3c6a-9792-76652db2e877/

U2 - 10.3390/molecules30234508

DO - 10.3390/molecules30234508

M3 - Article

C2 - 41375104

VL - 30

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 23

M1 - 4508

ER -