Dyes and Pigments (2020)
Update date:2022-08-29
Topics:
Cercená, Rodrigo
Dal-Bó, Alexandre Gon?alves
Rodembusch, Fabiano Severo
Silva Wakabayashi, Priscila Sayoko
Teixeira Alves Duarte, Luís Gustavo
Zapp, Eduardo
da Costa Duarte, Rodrigo
da Silveira Santos, Fabiano
Herein, we describe the syntheses of symmetric and asymmetric benzothiadiazole (BTD)-based fluorophores via the Sonogashira coupling reaction, using 4,7-dibromobenzothiadiazole as the central core and propargyl carbazole and/or propargyl diphenylamine as the side groups. The synthesized fluorophores exhibited absorption bands in the ultraviolet region, with a maxima between 372 and 380 nm due to the π→π* electronic transitions. Although they presented very low fluorescence quantum yields in solution, they demonstrated typical aggregation-induced emission phenomenon. Their oxidation potentials ranged from 0.91 to 1.18 V vs. NHE and reduction potentials from ?1.20 to 1.26 V vs. NHE. Their HOMO energies ranged from ?5.35 to 5.62 eV electron affinity from ?3.18 to 3.24 eV. Thus, the electrochemical bandgap of the BTD-based fluorophores was in the range of 2.16–2.38 eV. The symmetric BTD derivatives 3 and 5 exhibited good thermal stability, with decomposition temperatures at ~330 °C and 200 °C, respectively. BTD 7 showed lower thermal stability with a decomposition temperature of ~110 °C. BTD 3 and 5 showed glass transition temperature (Tg) values of ~75 °C (first heating) and 60 °C (first and second heating), respectively. BTD 7 did not show any Tg. The density functional theory (DFT) and time-dependent DFT calculations were performed at the CAM-B3LYP/6-31G** level of theory, which corroborated with the charge transfer characteristics of these compounds.
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