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Usage

Uses

Used in Organic Electronics and Optoelectronics:
2,1,3-Benzoselenadiazole is used as a component in the development of organic electronic and optoelectronic devices due to its promising electronic and photophysical properties. Its unique structure allows for the creation of materials with tailored properties for use in various applications, such as organic light-emitting diodes (OLEDs), organic solar cells, and organic field-effect transistors (OFETs).
Used in Material Synthesis:
2,1,3-Benzoselenadiazole is used as a building block in the synthesis of novel materials for various technological applications. Its incorporation into different chemical structures can lead to the development of new materials with improved properties, such as enhanced stability, conductivity, or specific interactions with other molecules.
Used in Pharmaceutical Research:
2,1,3-Benzoselenadiazole is used as a subject of research in the pharmaceutical field due to its potential bioactivity and medicinal properties. Its unique structure and electronic properties may contribute to the development of new drugs or drug candidates with novel mechanisms of action or improved therapeutic effects.
Used in Chemical Research:
2,1,3-Benzoselenadiazole is used as a subject of study in chemical research to explore its properties, reactivity, and potential applications. Understanding its behavior in various chemical reactions and interactions can provide insights into the development of new synthetic routes, catalysts, or other chemical processes that utilize 2,1,3-Benzoselenadiazole.

InChI:InChI=1/C6H4N2Se/c1-2-4-6-5(3-1)7-9-8-6/h1-4H

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 55293-87-3 benzo[1,2,5]selenadiazole 3-oxide 
• 74710-09-1 o-phenylenediamine sulphate 
• 7053-71-6 N-methyl-2,1,3-benzoselenodiazolium chloride 
• 14208-17-4 [1,2]benzoquinone (E,Z)-dioxime 

Downstream Products

• 767-65-7 4-amino-2,1,3-benzoselenadiazole 
• 1074-21-1 5-amino-2,1,3-benzoselenadiazole 
• 54107-99-2 dimethyl quinoxaline-2,3-dicarboxylate 
• 126970-63-6 IrCl₂(H)(PPh₃)2(2,1,3-benzoselenadiazole) 
• 128817-72-1 trans(benzoselenadiazole-N)carbonylchlorohydridobis(triphenylphosphine)ruthenium(II) 
• 128817-72-1 {RuClH(CO)(benzo-2,1,3-selenadiazole)(PPh₃)2} 
• 213336-57-3 [RuHCl(CS)(2,1,3-benzoselenadiazole)(PPh₃)2] 
• 1000398-38-8 [Ru(CH=CH₂)Cl(CS)(2,1,3-benzoselenadiazole)(PPh₃)2] 
• 95-54-5 1,2-diamino-benzene 
• 608-32-2 1,2,3-triaminobenzene 
• 534591-72-5 4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]selenadiazole 

Relevant academic research and scientific papers

Highly Efficient Luminescent Solar Concentrators Based on Benzoheterodiazole Dyes with Large Stokes Shifts

Five extended π-conjugated systems with electron donor (D) and acceptor (A) moieties have been synthesized. Their basic D-A-D structural motif is a benzothiadiazole unit symmetrically equipped with two thiophene rings (S2T). Its variants include 1) the same molecular framework in which sulfur is replaced by selenium (Se2T), also with four thiophene units (Se4T) and 2) a D’-D-A-D system having a N-carbazole donor moiety at one end (CS2T) and a D’-D-A-D-A’ array with a further acceptor carbonyl unit at the other extremity (CS2TCHO). The goal is taking advantage of the intense luminescence and large Stokes shifts of the five molecules for use in luminescent solar concentrators (LSCs). All of them exhibit intense absorption spectra in the UV/Vis region down to 630 nm, which are fully rationalized by DFT. Emission properties have been studied in CH2Cl2 (298 and 77 K) as well as in PMMA and PDMS matrices, measuring photoluminescence quantum yields (up to 98 percent) and other key optical parameters. The dye–PMMA systems show performances comparable to the present state-of-the-art, in terms of optical and external quantum efficiencies (OQE=47.6 percent and EQE=31.3 percent, respectively) and flux gain (F=10.3), with geometric gain close to 90. LSC devices have been fabricated and tested in which the five emitters are embedded in PDMS and their wave-guided VIS luminescence feeds crystalline silicon solar cells.

Benzoselenadiazole-Based Conjugated Molecules: Active Switching Layers with Nanofibrous Morphology for Nonvolatile Organic Resistive Memory Devices

In this work, two symmetrical donor-acceptor-donor (D-A-D) type benzoselenadiazole (BSeD)-based π-conjugated molecules were synthesized and employed as an active switching layer for non-volatile data storage applications. BSeD-based derivatives with different donor units attached through common vinylene linkers showed different electrical and optical properties. 4,7-Di((E)-styryl)benzo[c][2,1,3]selenadiazole (DSBSeD) and 4,7-bis((E)-4-methoxystyryl)benzo[c][2,1,3]selenadiazole (DMBSeD) are sandwiched between gallium-doped ZnO (GZO) and metal aluminum electrodes respectively through solution-processed spin-coating method. The solution-processed nanofibrous switching layer containing the DMBSeD-based memory device showed reliable memory characteristics in terms of write and erase operations with low SET voltage than the random-aggregated DSBSeD-based device. The nanofibrous molecular morphology of switching layer overcomes the interfacial hole transport energy barrier at the interface of the DMBSeD thin-film and the bottom GZO electrode. The memory device GZO/DMBSeD/Al based on nanofibrous switching layers shows switching characteristics at compliance current of 10 mA with Vset=0.79 V and Vreset=?0.55 V. This work will be beneficial for the rational design of advanced next-generation organic memory devices by controlling the nanostructured morphology of active organic switching layer for enhanced charge-transfer phenomenon.

Tetraphenylene-Coated Near-Infrared Benzoselenodiazole Dye: AIE Behavior, Mechanochromism, and Bioimaging

A D-A-D type of tetraphenylene-coating benzoselenodiazole fluorescence dye with near-infrared emission has been designed and constructed. This dye shows an obvious aggregation-induced-emission behavior. In the solid state, it exhibits a reversible mechanochromism with the changes of near-infrared emission. Furthermore, this dye can be used to track the lysosomes of living cells and images in vivo.

Insights into the Aggregation Behaviour of a Benzoselenadiazole-Based Compound and Generation of White Light Emission

We have designed and synthesized the benzoselenadiazole (BDS) based donor-acceptor-donor (D-A-D) π-conjugated compound 4,7-di((E)styryl)benzo[2,1,3]selenadiazole (1). A single-crystal study of 1 shows J-type molecular aggregation in the solid state. The crystal packing of 1 shows head-to-head dimeric intermolecular assembly via Se???N interactions while staircase-type interlock molecular packing has occurred via Se???π interaction. The staircase-type interlock packing of dimeric molecular arrangement induces sheet-type, herringbone type architecture along crystallographic a axis and ab plane via CH???π interactions. Interestingly, the J-type aggregation of 1 in solid state changes to H-type aggregation upon UV-irradiation. Moreover, our spectroscopic findings in solution state reveal H-type of aggregation of 1 in 90 % aqueous THF. We have further demonstrated white light emission in the binary mixture of 1 and 1-pyrenemethanol (2) in 90 % aqueous THF. Our study reveals solvent specific co-assembly of H-aggregated 1 and 2 in 90 % aqueous THF solution, which shows white light emissive properties with the Commission Internationale de l'Eclairage (CIE) chromaticity coordinates (0.32, 0.31). The observed white light emission arises mainly due to the combination of red light from H-aggregated 1, blue light from monomeric 2 and green light from excimers of 2.

Effective modulation of the photoluminescence properties of 2,1,3-benzothiadiazoles and 2,1,3-benzoselenadiazoles by Pd-catalyzed C-H bond arylations

A one step procedure towards the synthesis of 4-aryl-2,1,3-benzothiadiazoles, 4,7-diaryl-2,1,3-benzothiadiazoles and 4-aryl-2,1,3-benzoselenadiazoles using palladium-catalyzed regioselective C-H bond arylations of 2,1,3-benzothiadiazole and 2,1,3-benzoselenadiazole was developed. A donor-acceptor compound was also synthesized via two successive C-H bond arylations at C4 and C7 positions of the 2,1,3-benzothiadiazole unit. One of the major achivements of this methodology arises from the fine modulation of the fluorescence wavelength with emission colors covering blue to red regions of the visible spectrum by the simple introduction of the suitable aryl group on the 2,1,3-benzothiadiazole unit.

(AZA)INDOLE-, BENZOTHIOPHENE-, AND BENZOFURAN-3-SULFONAMIDES

Disclosed are sulfonamide compounds with GPR17 modulating properties, which are useful for treating or preventing a variety of CNS and other diseases, in particular for preventing and treating myelinating diseases or disorders.

Supramolecular Synthesis Based on a Combination of Se?N Secondary Bonding Interactions with Hydrogen and Halogen Bonds

Examination of the solid state structures of 2,1,3-benzoselenadiazole complexes with hydrogen or halogen bond donors has demonstrated that the 2,1,3-benzoselenadiazole molecules preferably form centrosymmetric dimers with use of [Se-N]2 supramolecular synthon, whereas the two remaining nitrogen atoms not involved in the [Se-N]2 supramolecular interactions can act as acceptors of hydrogen or halogen bonds. Cocrystallization of selenadiazoles with monofunctional hydrogen or halogen bond donors like pentafluorophenol, pentafluorobenzoic acid, or pentafluoroiodobenzene results in formation of binary discrete complexes. One- or two-dimensional aggregates based on selenadiazole [Se-N]2 dimers as building blocks were prepared using bifunctional hydrogen or halogen bond donors like resorcinol, tetrafluororesorcinol, tetrafluorohydroquinone, and 1,4-diiodotetrafluorobenzene. During the complexation of selenadiazoles with hydroquinone, anilic acid, or chloranilic acid a competition between Se?N and Se?O interactions resulted in breaking of the [Se-N]2 synthon.

Synthetic, structural, and computational investigations of N-alkyl benzo-2,1,3-selenadiazolium iodides and their supramolecular aggregates

Despite their versatility, the application of telluradiazoles as supramolecular building blocks is considerably constrained by their sensitivity to moisture. Albeit more robust, their selenium analogues form weaker supramolecular interactions. These, however, are enhanced when one nitrogen atom is bonded to an alkyl group. Here we investigate general methods for the synthesis of such derivatives. Methyl, iso-propyl and tert-butyl benzo-2,1,3-selenadiazolium cations were prepared by direct alkylation or cyclo-condensation of the alkyl-phenylenediamine with selenous acid. While the former reaction only proceeds with the primary and tertiary alkyl iodides, the latter is very efficient. Difficulties reported in earlier literature are attributable to the formation of adducts of benzoselenadiazole with its alkylated cations and side reactions initiated by aerobic oxidation of iodide. However, the cations themselves are resilient to oxidation and stable in acidic to neutral aqueous medium. X-ray crystallography was used in the identification and characterization of the following compounds: [C6H4N2(R)Se]+X-, (R = CH(CH3)2, C(CH3)3; X = I-, I3-], [C6H4N2(CH3)Se]+I-, and [C6H4N2Se][C6H4N2(CH3)Se]2I2. Formation of Se?N secondary bonding interactions (chalcogen bonds) was only observed in the last structure as anion binding to selenium is a strong competitor. The relative strengths of those forces and the structural preferences they enforce were assessed with DFT-D3 calculations supplemented by AIM analysis of the electron density.

Effects of Donor and Acceptor Units Attached with Benzoselenadiazole: Optoelectronic and Self-Assembling Patterns

Here, we report the effects of electron donor and acceptor units attached with benzoselenadiazole for the change in optoelectronic and packing patterns in solid states. We have synthesized 4-methoxybenzene, naphthalene, and 4-nitrobenzene capped benzoselenadiazoles (compounds 1-3 respectively) and studied their photophysical as well as electrochemical properties. All three molecules show two absorption bands (π-π transition band and CT-band). Three molecules (1-3) show orange, yellow-green, and green colors in dichloromethane solutions upon irradiation of UV light at 365 nm. Benzoselenadiazole-based compounds 1-2 form head to head dimers via Se···N interactions in the solid states. Compounds 1 and 2 show interlock type packing via Se···N interaction in their solid state structures. Se···π interaction takes a major role to form interlocked sheet type structures in crystal packing of compound 1, whereas Se···N, N···N, and CH···π interactions help to form a supramolecular sheet type of structure in the crystal packing of compound 2. Band gaps of these compounds were tuned by changing the electron donating to electron withdrawing units attached with a benzoselenadiazole core.

Selenadiazole derivatives as theranostic agents for simultaneous cancer chemo-/radiotherapy by targeting thioredoxin reductase

The lack of early and timely diagnosis of tumors and the monitoring of their response to therapeutics have limited the successful cancer treatments. Theranostic agents are expected to realize the dual-purpose of simultaneous diagnosis and therapy for treatments of cancers. In the present study, we have examined the effects of the chemical structure of selenadiazole derivatives (SeDs) on their anticancer efficacy and radio-sensitization against clinically used X-rays. The results showed that the introduction of a nitro group (-NO2) into SeD-3 significantly enhanced the anticancer activity of SeDs. The higher lipophilicity endowed SeD-3 with higher cellular internalization ability, resulting in higher cellular uptake and anticancer efficacy. Specifically, the capacity of autofluorescence allowed the use of SeD-3 as a promising theranostic agent to directly monitor the cellular uptake, localization and biodistribution in vitro and in vivo. Interestingly, SeD-3 also significantly enhanced the sensitivity of HeLa cervical cells to X-ray-induced apoptosis by targeting the inhibition of TrxR and promoting intracellular ROS overproduction, which activated the downstream ROS-mediated signaling pathways to regulate cell apoptosis. Furthermore, SeD-3 exhibited satisfactory in vivo antitumor efficacy through the inhibition of tumor proliferation and induction of tumor cell apoptosis, and showed no toxicity to the main organs. Moreover, from the results of hematological analysis, we found that not only inhibiting the tumor growth, treatment of SeD-3 also alleviated the damage of liver, kidney and heart function of nude mice induced by HeLa xenografts. Taken together, this study demonstrates that SeDs could be further developed as an effective and safe theranostic agent for simultaneous cancer chemo-/radiotherapy.