New photoactive D-π-A-π-D benzothiadiazole derivative: Synthesis, thermal and photophysical properties

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

“…In contrast, the excitation and absorption spectra are no longer superimposable when species exist in different forms, such as aggregates, in the ground state (Valeur, 2012). When compared with similar benzothiadiazole derivatives previously reported by our group (Westrup et al, 2016), the benzoxadiazole-based compounds 9a-d showed a greater tendency toward aggregate formation. This could be associated with the benzoxadiazole moiety and the higher dipole moment of this heterocycle (Tobiason et al, 1973).…”

“…As part of our continued involvement in the chemistry of Nheterocycles (Saba et al, 2015(Saba et al, , 2016(Saba et al, , 2017(Saba et al, , 2018(Saba et al, , 2020Rafique et al, 2016Rafique et al, , 2018aSilva et al, 2017;Bettanin et al, 2018;Peterle et al, 2018;Rodigues et al, 2018;Tornquist et al, 2018;Meirinho et al, 2019;Neto et al, 2020;Scheide et al, 2020) and material sciences (Frizon et al, 2014(Frizon et al, , 2015(Frizon et al, , 2016(Frizon et al, , 2018Bo et al, 2016Bo et al, , 2018Westrup et al, 2016;Matzkeit et al, 2018;Regis et al, 2018), herein, we report the synthesis and characterization of BOX derivatives containing electrondonor groups (alkylated tetrazole rings) connected to the 2,1,3-BOX group as an electron-acceptor unit. In addition, thermal, electrochemical, and theoretical predictions were made and photophysical analysis was performed to study the stability, likely geometry, and luminescence properties of these compounds in their ground and excited electronic states.…”

Effects of the acceptor pattern and substitution position on the properties of N-phenyl-carbazolyl based donor–acceptor–donor molecules

“…With the increase in solvent polarity, the emission peaks exhibited large redshis (ranging from 31 to 58 nm), displaying a signicant solvatochromic effect. [31][32][33][34] This phenomenon might be related to the inherent ICT in the D-A molecules. Many studies have shown that ICT was strengthened upon excitation, which increases the molecular dipole moment.…”

Synthesis, DNA Interaction and Genotoxic Evaluation of a Photoactive Benzothiadiazole with Potential Application in Photovoltaic Paint

“…Synthetic route used to produce benzothiadiazole (7). 51 A vibrational mode that is due to aliphatic stretching bands of the C 12 H 25 moieties is present for all compounds and is indicative of alkyl chains bound to the tetrazole ring. For compound 3, the stretching band of the OH group is located at 3310 cm -1 , indicating a coupling between the aryl bromide 3 and 2-methyl-3-butyne-2-ol.…”

“…The benzothiadiazole compound 7 was obtained using a previously described 51 synthetic method by reacting the 4,7-dibromo-2,1,3-benzothiadiazole (6) with the terminal alkyne 4 in a Sonogashira coupling reaction (Scheme 1). Figure 1 shows the infrared absorption spectra for the precursors (3-4) and the final compound (7).…”