1887-60-1

Usage

Uses

Used in Organic Synthesis:
5,6-Dimethylbenzo-2,1,3-thiadiazole is used as a building block in organic synthesis for the creation of various chemical compounds. Its unique structure and properties make it a valuable component in the synthesis of complex organic molecules.
Used in Material Science:
In material science, 5,6-Dimethylbenzo-2,1,3-thiadiazole is used for the development of advanced materials with specific properties. Its high thermal stability and aromatic nature contribute to the creation of materials with improved performance characteristics.
Used in Electronics:
5,6-Dimethylbenzo-2,1,3-thiadiazole is used as a component in the development of electronic devices due to its potential applications in organic semiconductors. Its properties make it suitable for use in electronic components, such as transistors and sensors.
Used in Optoelectronics:
In the field of optoelectronics, 5,6-Dimethylbenzo-2,1,3-thiadiazole is utilized for the development of materials with light-emitting or light-absorbing properties. Its incorporation into optoelectronic devices can enhance their performance and efficiency.
Used in Photovoltaics:
5,6-Dimethylbenzo-2,1,3-thiadiazole is used in the development of photovoltaic materials, such as solar cells. Its properties contribute to the improvement of solar cell efficiency and stability.
Used in Pharmaceutical Research and Drug Development:
5,6-Dimethylbenzo-2,1,3-thiadiazole may have biological properties, making it a potential candidate for pharmaceutical research and drug development. Its unique structure and properties could be explored for the development of new drugs and therapeutic agents.

InChI:InChI=1/C8H8N2S/c1-5-3-7-8(4-6(5)2)10-11-9-7/h3-4H,1-2H3

Upstream product

• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 222851-56-1 N-phenylsulfinylamine 

Downstream Products

• 28681-49-4 4,7-dibromo-5,6-dimethylbenzo[c][1,2,5]thiadiazole 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 67130-14-7 1,2-diamino-3,4,5,6-tetramethylbenzene 
• 106148-67-8 4,5,6,7-tetramethylbenzimidazole 
• 106148-68-9 2-benzyl-4,5,6,7-tetramethylbenzimidazole hydrochloride 
• 24793-64-4 5,6-dibenzyl-benzo[1,2,5]thiadiazole 
• 24793-66-6 5,7-diphenyl-5H,7H-thieno[3',4':4,5]benzo[1,2-c][1,2,5]thiadiazole 
• 24793-65-5 C,C'-diphenyl-C,C'-benzo[1,2,5]thiadiazole-5,6-diyl-bis-methanone 
• 24793-67-7 5,7-diphenyl-5H,7H-thieno[3',4':4,5]benzo[1,2-c][1,2,5]thiadiazole 6-oxide 
• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 

Relevant academic research and scientific papers

Functionalizing benzothiadiazole with non-conjugating ester groups as side chains in a donor-acceptor polymer improves solar cell performance

Herein, the effect of non-conjugated ester functionalization at the 5,6-position of 2,1,3-benzothiadiazole (BT) in a donor (D)-acceptor (A) conjugated polymer (CP) used for photovoltaic devices has been investigated. Positions 5 and 6 of BT were functionalized with methyl acetate groups and the structure property relationship was compared to BT with methyl groups at the 5 and 6 positions in four types of D-A CPs. Alternate co-polymers of newly synthesized methyl and methyl acetate derivatives of BT and Th-BT-Th with commonly used donors such as dithiophene (DTh) and benzodithiophene (BDT) were synthesized using Stille coupling reactions: namely, P(1,2,3,4)-Me and P(1,2,3,4)-Ac. All CPs were extensively characterized using GPC, UV-visible, 1H-NMR, 13C-NMR, TGA and CV. The optimized geometry, along with changes in the dihedral angle upon substitution with acetate groups, was analyzed by density functional theory (DFT) using B3LYP/6-31G(d,p). The side chain ester groups lower the dihedral angle, improve the optical and electrochemical properties of CPs in polymer solar cells (PSCs), improve phase separation of the active layer and performance of the fabricated PSCs compared to methyl counterparts, as investigated for P(1,2,3,4)-Me and P(1,2,3,4)-Ac. Upon fabrication of a BHJ solar cell with ITO/PEDOT:PSS/P-PC71BM/LiF/Al device geometry, CPs with methyl acetate functionalization (P2-Ac, P3-Ac and P4-Ac) resulted in higher PCEs of 1.36%, 1.17% and 0.35%, compared to their methyl counterpart CPs, P2-Me, P3-Me and P4-Me, which exhibited PCEs of 0.9%, 0.54% and 0.31%, respectively. With 1,8-diiodooctane (DIO) as an additive, a higher PCE of 1.96% was achieved for P3-Ac. Atomic force microscopy (AFM) and thin film X-ray diffraction (XRD) were used to determine the impact of side chain ester groups on π-π stacking distance among CP main chains in the film state and the morphology of the active layer of the fabricated PSCs, respectively.

Pentacenobis(thiadiazole)dione, an n-type semiconductor for field-effect transistors

A new heteroacenequinone, pentaceno[2,3-c:9,10-c′]bis([1,2,5] thiadiazole)-6,13-dione (PBTDQ), with two peripheral thiadiazole rings was synthesized, and its solid-state properties were characterized. The fused planar structure with a low-lying LUMO and low reorganization energy facilitates electron transport, affording μe values of up to 0.11 cm 2 V-1 s-1 in field-effect transistor devices.

Synthesis and photovoltaic properties of novel C60 bisadducts based on benzo[2,1,3]-thiadiazole

A novel C60 solar cell acceptor (BTOQC, benzo[2,1,3]-thiadiazole-o-quinodimethane-C60 bisadducts) based on benzo[2,1,3]thiadiazole has been synthesized as model to study how the thiadiazole group will affect the device performance in bulk heterojunction organic photovoltaics (BHJ-OPV) with poly(3-hexylthiophene) (P3HT) as donor. The optoelectronic, electrochemistry, and photovoltaic properties of the novel bisadduct BTOQC have been fully investigated. The best device performance of this fullerene derivative in our research was obtained as 2.50% with a high Voc of 0.74 V.

Role of cyano substituents on thiophene vinylene benzothiadiazole conjugated polymers and application as hole transporting materials in perovskite solar cells

Two narrow-band gap of donor-acceptor based conjugated polymers, BTTP and BTTP-CN were synthesized by Wittig copolymerization with thiophene or cyano-vinylene thiophene as the donor and 2,1,3-benzothiadiazole as acceptor units. The polymers were investigated by FT-IR, UV-V is, fluorescence spectroscopy, thermal stability and cyclic voltammetry (CV). The thermal analysis revealed that the BTTP polymer was stable up to 220 °C and BTTP-CN was stable up to 254 °C. The absorption spectra showed absorption maxima at 403 nm for BTTP and 397 nm for BTTP-CN. The polymers BTTP exhibited orange colour fluorescence emission at 585 nm and BTTP-CN exhibited yellow color fluorescence emission at 520 nm. The optical band gap values of undoped polymers BTTP and BTTP-CN were calculated as 2.2 and 2.13 eV respectively. Novel synthesized polymers were then enforced as dopant/additive-free hole transport materials in perovskite solar cells. Both polymers has shown the photovoltaic performance of 3.80 % for BTTP and 3.48 % for BTTP-CN under 1 sun illumination. The photovoltaic performance are compared with reference hole transporting material of spiro-OMeTAD with and without additive as 12.53 and 7.55% respectively.

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

Chalcogen bonding (CB) is the focus of increased attention for its applications in medicinal chemistry, materials science, and crystal engineering. However, the origin of sulfur's recognition properties remains controversial, and experimental evidence for supporting theories is still emerging. Here, a comprehensive evaluation of sulfur CB interactions is presented by investigating 2,1,3-benzothiadiazole X-ray crystallographic structures gathered from the Cambridge Structure Database (CSD), Protein Data Bank (PDB), and own laboratory findings. Through the systematic analysis of substituent effects on a subset library of over thirty benzothiadiazole derivatives, the competing interactions have been categorized into four main classes, namely 2S–2N CB square, halogen bonding (XB), S???S, and hydrogen-bonding (HB). A geometric model is employed to characterize the 2S–2N CB square motifs and discuss the role of electrostatic, dipole, and orbital contributions toward the interaction.

A field-effect transistor with the nature of the material and its preparation method (by machine translation)

The invention discloses a material with organic field effect transistor properties and a preparation method thereof. The material is pentacene[2,3-c:9,10-c']di([1,2,5] thiadiazole)-6,13-diketone. The preparation method comprises the following steps: preparing 4,5-dimethyl benzo[c][1,2,5] thiadiazole; preparing 4,5-dibromomethyl benzo[c][1,2,5] thiadiazole; synthesizing benzo[c][1,2,5] thiadiazole-4,5-dimethylene diacetatediacetate; synthesizing 4,5-dihydroxymethyl benzo[c][1,2,5] thiadiazole; synthesizing 4,5-diformaldehyde benzo[c][1,2,5] thiadiazole; synthesizing pentacene[2,3-c:9,10-c']di([1,2,5] thiadiazole)-6,13-diketone. The pentacene[2,3-c:9,10-c']di([1,2,5] thiadiazole)-6,13-diketone disclosed by the invention has the properties of an organic field effect transistor, so that the migration rate of films and crystals is higher, and a way is provided for improving the performances of semiconductor molecules of various types.

Synthesis and characterization of carbazole-based copolymers containing benzothiadiazole derivative for polymer light-emitting diodes

A new thermally robust electroluminescent (EL) carbazole-based-conjugated copolymer, including poly[3,7-(N-hexylcarbazole)-co-4,7-{5,6-bis(3,7- dimethyloctylo-xymethyl)-2,1,3-(benzothiadiazole)}] (PCz-co-P2C10BT) was synthesized and used to fabricate the efficient polymer light-emitting diodes (PLEDs). The glass transition temperature of the PCz-co-P2C 10BT (105C) was found to be higher than that of poly(9,9- dialkylfluorene) derivatives. We fabricated PLEDs in ITO/PEDOT/light-emitting polymer/Alq3/LiF/Al configuration. The new copolymer was found to have green emission color (523nm). The maximum brightness and external quantum efficiency of PCz-co-P2C10BT were 260 cd/m2 at 14V and 0.22%, respectively.