20138-79-8

Usage

Uses

Used in Organic and Materials Chemistry:
2,1,3-Benzothiadiazole-4,7-dicarbonitrile is used as a key building block for the synthesis of organic semiconducting materials. Its conjugated structure endows it with unique electronic properties that are highly valuable in the development of advanced materials for electronic applications.
Used in Organic Electronic Devices:
In the field of organic electronics, 2,1,3-Benzothiadiazole-4,7-dicarbonitrile is utilized as a component in the creation of organic light-emitting diodes (OLEDs). Its electronic properties make it a suitable material for enhancing the performance and efficiency of these devices.
Used in Organic Photovoltaics:
2,1,3-Benzothiadiazole-4,7-dicarbonitrile also finds application in organic photovoltaics (OPVs), where it contributes to the light absorption and charge transport properties of the solar cells, thereby improving their energy conversion efficiency.
Used in Medicinal Chemistry:
Furthermore, 2,1,3-Benzothiadiazole-4,7-dicarbonitrile has been explored for its potential in medicinal chemistry. It is studied for its capacity to be incorporated into the development of new pharmaceutical compounds, leveraging its unique structure to target specific biological activities or therapeutic effects.

Upstream product

• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 557-21-1 zinc(II) cyanide 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 95-54-5 1,2-diamino-benzene 
• 544-92-3 copper(I) cyanide 
• 23616-25-3 4,7-dibromobenzo[d][l,2,3]thiadiazole 

Downstream Products

• 79780-61-3 1,2-diamino-3,6-dicyanobenzene 
• 1377975-50-2 C₄₄H₅₃N₆O₇PS 
• 5170-41-2 2,1,3-benzothiadiazole-4,7-dicarboxylic acid 

Relevant academic research and scientific papers

Two 3D Cd(II) Metal-Organic Frameworks Linked by Benzothiadiazole Dicarboxylates: Fantastic S@Cd6 Cage, Benzothiadiazole Antidimmer, and Dual Emission

On the basis of the same benzothiadiazole (BTD) ligand 2,1,3-benzothiadiazole-4,7-dicarboxylic acid (H2L), two new isomers of three-dimensional (3D) BTD-derived Cd(II) metal-organic frameworks 1-2 {[S@Cd6L6]·xH2O}n were obtained by the different solvothermal reactions, which were structurally similar. Surprisingly, structural analyses reveal that in 1 or 2, one free sulfur atom was fixed in a Cd(II) cluster cage by strong intermolecular interaction to form the secondary building unit (SBU) S@Cd6. Each SBU S@Cd6 is connected by six L2- ligands and further extended into the 3D porous framework. In this work, the BTD antidimmer was evidenced by structural analysis and photophysical study. Furthermore, either 1 or 2 showed the uncommon dual emission, while only one emission was observed in the solution of ligand H2L. The dual-emission mechanism was also realized by the structural analysis and photophysical study. Interestingly, although there is slight difference in structure (regular octahedral cage in 1 and slightly distorted octahedral cage in 2), the changes in N2 adsorption capability and photophysical performance between 1 and 2 are obvious, where 2 shows smaller Brunauer-Emmett-Teller surface area, broader absorption of antidimmer, and longer dual-emission lifetimes. Interestingly, either 1 or 2, the dual emission was clearly red-shifted by increasing the solvent polarity or the acidity of ambience, respectively.

Photochemical Electron Transfer across Surfactant Bilayers mediated by 2,1,3-Benzothiadiazole-4,7-dicarbonitrile

2,1,3-Benzothiadiazole-4,7-dicarbonitrile (BTDN) has been photochemically reduced by 4-morpholine-ethanesulphonic acid (MES) in the presence of vesicles of dioctadecyldimethylammonium bromide (DODAB) or egg yolk phosphatidylcholine containing DODAB.Using asymmetrical vesicles, electron transfer can occur from MES entrapped within the inner water pools to suitable anthraquinonesulphonates (1; 1,5; 2,6 but not 2) in the bulk water mediated by BTDN.Evidence is presented that these reactions involve the genuine transport of the electron across the bilayer and not leakage of either donor or acceptor across the bilayer.Kinetic and flash photolysis studies show that the rate-determining step of the reaction is electron transport across the vesicle, that this occurs by diffusion of BTDN*- and that the rate of this diffusion reaction is in turn controlled by the charge-compensating diffusion of OH- in the opposite direction across the bilayer.

Multi PCET in symmetrically substituted benzimidazoles

Proton-coupled electron transfer (PCET) reactions depend on the hydrogen-bond connectivity between sites of proton donors and acceptors. The 2-(2′-hydroxyphenyl) benzimidazole (BIP) based systems, which mimic the natural TyrZ-His190 pair of Photosystem II

Pushing to the low limits: Tetraazaanthracenes with very low-lying LUMO levels and near-infrared absorption

Here we propose the combination of the 4-alkoxythiazole donor motif with highly photostable tetraazaanthracenes as electron-acceptor units. The segregated frontier orbitals in these dyes afford optical band gaps of 1.4-1.1 eV. Cyclic voltammetry confirmed the very low-lying LUMO levels that are attributed to the highly electron-deficient tetraazaanthracene moiety.

The Photochemical Reduction of 2,1,3-Benzothiadiazole-4,7-dicarbonitrile in the Presence of Cationic Micelles, and Onward Electron-transfer Reactions

Photolysis of solutions containing 2,1,3-benzothiadiazole-4,7-dicarbonitrile (BTDN) ethylenediaminetetra-acetic acid disodium salt (EDTA) and cetyltrimethylammonium bromide (CTAB) micelles at pH 5.5 produces the radical anion, BTDN.-, with BTDN acting both as an electron acceptor and as a chromophore.Variations in the efficiency of this reaction with pH, and are interpreted in terms of the formation of a complex between EDTA and BTDN which is broken down by the micelles.Net electron transfer does not occur within the complex.Alternative electron donors such as triethanolamine (TEOA) or 4-morpholine-ethanesulphonic acid (MES) can be employed, but not ascorbic acid or sulphite ion.The use of BTDN.- to reduce anthraquinones in stoichiometric or catalytic (with continuous photolysis) reactions is described.This allows an estimate of the redox potential of BTDN/BTDN.- when incorporated into micelles.

Unique structural micro-adjustments in a new benzothiadiazole-derived Zn(II) metal organic framework: Via simple photochemical decarboxylation

The first example of micro-adjustments of a metal organic framework (MOF) structure was observed in a new Zn(ii) MOF (Zn-BTDC-M1) derived from a benzothiadiazole-4,7-dicarboxylic acid (H2BTDC) ligand using a light-driven decarboxylation process. Interestingly, such decarboxylation occurs at the non-chelated wing of the ligand, which induced a change in the capability of the MOF for physical N2 adsorption and chemical NH3 gas adsorption.

Small Organic Molecule Based on Benzothiadiazole for Electrocatalytic Hydrogen Production

A small organic molecule 2,1,3-benzothiadiazole-4, 7-dicarbonitrile (BTDN) is assessed for electrocatalytic hydrogen evolution on glassy carbon electrode and shows a hydrogen production Faradaic efficiency of 82% in the presence of salicylic acid. The key catalytic intermediates of reduced species BTDN–? and protonated intermediates are characterized or hypothesized by using various spectroscopic methods and density functional theory (DFT)-based calculations. With the experimental and theoretical results, a catalytic mechanism of BTDN for electrocatalytic H2 evolution is proposed.

Covalent Triazine Framework Nanoparticles via Size-Controllable Confinement Synthesis for Enhanced Visible-Light Photoredox Catalysis

For metal-free, organic conjugated polymer-based photocatalysts, synthesis of defined nanostructures is still highly challenging. Here, we report the formation of covalent triazine framework (CTF) nanoparticles via a size-controllable confined polymerization strategy. The uniform CTF nanoparticles exhibited significantly enhanced activity in the photocatalytic formation of dibenzofurans compared to the irregular bulk material. The optoelectronic properties of the nanometer-sized CTFs could be easily tuned by copolymerizing small amounts of benzothiadiazole into the conjugated molecular network. This optimization of electronic properties led to a further increase in observed photocatalytic efficiency, resulting in total an 18-fold enhancement compared to the bulk material. Full recyclability of the heterogeneous photocatalysts as well as catalytic activity in dehalogenation, hydroxylation and benzoimidazole formation reactions demonstrated the utility of the designed materials.

Direct Conversion of Benzothiadiazole to Benzimidazole: New Benzimidazole-Derived Metal–Organic Frameworks with Adjustable Honeycomb-Like Cavities

Up to now, the direct conversion of the thiadiazole ring to other heterocyclic rings has been a very challenging task. Herein, a CdII-mediated alcohol-substitution strategy for direct conversion from benzothiadiazole to benzimidazole is reported. Experimental and molecular modeling studies on the role of the chelated metal ion in this in situ alcohol-substitution reaction revealed that it serves as an all-rounder that is involved in the insertion of alcohol, activation of the thiadiazole ring by coordinative interaction, and the sulfur-extrusion process. Interestingly, the insertion of alcohol occurs much earlier than the sulfur-extrusion process, supported by a water-mediated proton-transfer process. This strategy also is suitable for constructing new benzimidazole-derived MOFs [Cd2(HMBIDC2?)2]?4 H2O (Cd-BID-MOF-1, HMBIDC2?=2-methyl-1H-benzimidazole-4,7-dicarboxylate) and [Cd2(HPBIDC2?)2]?1/3 H2O (Cd-BID-MOF-2, HPBIDC2?=2-(3-hydroxypropyl)-2H-benzimidazole-4,7-dicarboxylate). Because the terminal hydroxyl group on the imidazole ring protrudes into the circular channel in rhombohedral Cd-BID-MOF-2, the cavity is closer to hydrophilic than the honeycomb-like cavity in Cd-BID-MOF-1 with similar 3D structure. This rare observation will provide a new strategy to develop in situ ligand-reaction synthesis of functional MOFs and useful chelation-assisted catalytic reactions in heteroaromatic chemistry.

A Small Push-Pull Fluorophore for Turn-on Fluorescence

A new class of push-pull dyes is reported based on the structures of benzoxa- and benzothiadiazole heterocycles. This new class of dyes displays red-shifted wavelengths of emission and greater sensitivity to polarity and hydrogen bonding solvents relative to previously known derivatives.