2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules

Abstract

2,1,3‐Benzothiadiazole (BTD) is one of the most important nuclei used in the chemistry of photoluminescent compounds and applicable for light technology. The understanding of its properties and reactions is fundamental for the design and application of these derivatives in molecular organic electronic devices and for other technologies. As a result of their potential as constituents of organic light‐emitting diodes, solar cells, liquid crystals, dyes, photovoltaic cells, and many others, attention has been focused on BTD π‐extended derivatives with potential use in this exciting area. Herein, we describe their syntheses, properties, reactions, and selected examples of applications in light technology using by BTD (small molecules) as the core.

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

“…20 Benzothiadiazole (BT) is one of the most important classes of electron acceptors due to its relatively high electron affinity and p-extended planar structure. 21 Recently, uorina-tion of BT has been utilized and shown to be an efficient means to modify the optical, electronic and electrochemical properties of BT. 22,23 Tang and coworkers have synthesized the electron donor-acceptor-donor (D-A-D) chromophores containing BT derivatives and TPE.…”

Dipyrido[3,2‐a:2′,3′‐c]phenazine‐Based Donor–Acceptor Aromatic Heterocyclic Compounds with Thienyl and Triphenylamino Chromophores at the 2,7‐ and/or 10,13‐Positions

“…In conclusion, compared with our previous work, this family of D-A compounds (6)(7)(8)(9)(10)(11)(12)(13)(14)(15) exhibits favorable photophysical properties.…”

“…[15] It is also used as a key intermediate for the synthesis of photoluminescent quinoxaline derivatives. [16] In our work, a series of T-and H-shaped DPPZ-centered semiconducting fluorescent compounds were prepared by the synthetic route shown in Scheme 1, whereas 1,10-phenanthroline-5,6-dione derivatives [17a-d] and 2,7-dibromodipyrido [3,2-a:2',3'-c]phenazine [17e,f] were synthesized according to the previously reported approaches.…”

Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles

“…For these reasons, 2,1,3-benzothia/selenadiazoles found numerous applications as electron-acceptor or/and luminescent building blocks of real or potential molecular functional materials for electronics, optoelectronics and photovoltaics. 4,5,[13][14][15][16][17][18][19][20][21][22][23][24][25] Despite fluorinated (hetero) aromatics are promising for electronic and optoelectronic applications, 26,27 fluorinated 2,1,3-benzothia/selenadiazoles are less studied in this context. Hydrogen replacement by fluorine affects many properties of (hetero) aromatics including (hetero) aromaticity itself.…”