2255-80-3

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 7, p. 629, 1970 DOI: 10.1002/jhet.5570070324

Upstream product

• 1457-92-7 4-Methyl-2,1,3-benzothiadiazol 
• 601-87-6 3-methyl-2-nitroaniline 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 570-24-1 2-Methyl-6-nitroaniline 

Downstream Products

• 1026192-01-7 benzhydrylidene-(7-methyl-benzo[1,2,5]thiadiazol-4-yl)-amine 
• 3529-60-0 7-bromobenzo[c][1,2,5]thiadiazole-4-carboxylic acid 
• 1239277-96-3 4-bromo-7-dibromomethyl-2,1,3-benzothiadiazole 
• 1071224-34-4 7-bromobenzo[c][1,2,5]thiadiazole-4-carboxaldehyde 
• 1335150-10-1 2-((7-bromobenzo[c][1,2,5]thiadiazol-4-yl)methylene)malononitrile 
• 1335150-09-8 2-{[7-(5-(N,N-di-p-tolyl)aminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile 
• 1331742-86-9 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile 

Relevant academic research and scientific papers

Organic light-emitting material containing benzo[c][1,2,5]thiadiazole derivative receptor structural unit and application

The invention provides an organic light-emitting material based on a donor-receptor structure of a benzo[c][1,2,5]thiadiazole-4-aldehyde group receptor and a 2-(benzo[c][1,2,5]thiadiazole-4-methylene)malononitrile receptor and application thereof. The organic light-emitting material is a receptor-donor separation system, wherein the receptor is benzo[c][1,2,5]thiadiazole-4-aldehyde or 2-(benzo[c][1,2,5]thiadiazole-4-methylene) malononitrile, and a donor is carbazole and a derivative or benzoxazine and the like. The lowest unoccupied molecular orbital (LUMO) in the material is located in the receptor, and the highest occupied molecular orbital (HOMO) in the material is located in the donor, so that the molecular orbital energy level of the luminescent material can be effectively regulated and controlled through electrical regulation of the receptor structure and the donor. By regulating and controlling the structure of the light-emitting material or the electron donating capability of the donor, the light-emitting color of material molecules can be conveniently regulated. The organic light-emitting material has the characteristic that the light-emitting color is easy to adjust, andcan be used as a light-emitting material for preparing an OLED device.

Photoelectric conversion material and photoelectric conversion element

A photoelectric conversion material includes a compound represented by Formula (1), wherein, X is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, and a cyano group; and Y represents a monovalent substituent represented by Formula (2), wherein, R1 to R10 each independently represent a hydrogen atom, a deuterium atom, a halogen atom, an alkylgroup, or an aryl group; or two or more of R1 to R10 bond to each other to form one or more rings, and the remainders each independently represent a hydrogen atom, a deuterium atom, a halogen atom, analkyl group, or an aryl group; * denotes the binding site of Y in Formula (1); and Ar1 is selected from the group consisting of structures represented by Formulae (3), wherein ** denotes a binding site of Ar1 with N in Formula (2).

Surprising characteristics of D-A-type functional dyes by introducing 4-alkoxythiazoles as the donor-unit

In this study, we report on the syntheses of novel donor-acceptor molecules. These new dyes comprised benzo[c][1,2,5]thiadiazole and pendants with one or two 4-alkoxythiazoles as donor parts, which were introduced without Pd-catalyzed cross coupling reactions. The optical and electrochemical properties were studied via absorption, emission spectroscopy and cyclovoltammetric measurements. We experimentally found surprising small band gaps from HOMO to LUMO of 2.4 eV and 2 eV, respectively, which were also investigated using DFT calculations.

A rhodanine flanked nonfullerene acceptor for solution-processed organic photovoltaics

A novel small molecule, FBR, bearing 3-ethylrhodanine flanking groups was synthesized as a nonfullerene electron acceptor for solution-processed bulk heterojunction organic photovoltaics (OPV). A straightforward synthesis route was employed, offering the potential for large scale preparation of this material. Inverted OPV devices employing poly(3-hexylthiophene) (P3HT) as the donor polymer and FBR as the acceptor gave power conversion efficiencies (PCE) up to 4.1%. Transient and steady state optical spectroscopies indicated efficient, ultrafast charge generation and efficient photocurrent generation from both donor and acceptor. Ultrafast transient absorption spectroscopy was used to investigate polaron generation efficiency as well as recombination dynamics. It was determined that the P3HT:FBR blend is highly intermixed, leading to increased charge generation relative to comparative devices with P3HT:PC60BM, but also faster recombination due to a nonideal morphology in which, in contrast to P3HT:PC60BM devices, the acceptor does not aggregate enough to create appropriate percolation pathways that prevent fast nongeminate recombination. Despite this nonoptimal morphology the P3HT:FBR devices exhibit better performance than P3HT:PC60BM devices, used as control, demonstrating that this acceptor shows great promise for further optimization.

Property modulation of benzodithiophene-based polymers via the incorporation of a covalently bonded novel 2,1,3-benzothiadiazole-1,2,4-oxadiazole derivative in their main chain for polymer solar cells

Two new electron accepting monomers (BBOB and BOB) containing two serially connected different electron deficient units, such as 2,1,3-benzothiadiazole and 1,2,4-oxadiazole, were prepared and copolymerized with electron-rich benzodithiophene (BDT) derivative to afford polymers P(BDT-BBOB) and P(BDT-BOB), respectively. The optical band gaps of P(BDT-BBOB) and P(BDT-BOB) are calculated to be 2.32 eV and 1.99 eV, respectively, and their highest occupied molecular energy levels are determined to be -5.31 eV and -5.27 eV, respectively. Each of the newly synthesized polymers, i.e.P(BDT-BBOB) and P(BDT-BOB), is used as an electron donor, along with PC61BM as an electron acceptor, in the preparation of polymer solar cells (PSCs). The PSCs made with the configuration of ITO/PEDOT:PSS/P(BDT-BBOB) or P(BDT-BOB):PC61BM (1 : 2 wt%)/LiF/Al gave a maximum power conversion efficiency (PCE) of 1.76% and 2.46%, respectively, and the device performance was further improved to 3.31% and 4.21%, respectively, by simply treating the photoactive layer of PSCs with isopropyl alcohol. Overall, the opto-electrical and photovoltaic properties of the two polymers are found to be quite dependent on the configuration of the covalently bonded 2,1,3-benzothiadiazole and 1,2,4-oxadiazole units incorporated in the polymer main chain.

Stepwise unidirectional synthesis of oligo phenylene vinylenes with a series of monomers. Use in plastic solar cells

Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5- dipropoxyphenyl]vinyl}benzyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5- dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]vinyl}thiophene-2-ylmethyl) phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5- dipropoxyphenyl]vinyl}thiophene-2-ylmethyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5] thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.

Palladium-catalyzed amination with benzophenone imine as a new, safe and practical alternative to nitration for the synthesis of 7-amino-2,1,3-benzothiadiazoles

Palladium-catalyzed amination of 7-bromo-4 -methyl-2,1,3-benzothiadiazole (7) with benzophenone imine as an ammonia equivalent is described as a new, safe and practical alternative to nitration for the synthesis of 7-amino-4-methyl-2,1,3-benzothiadiazole