102183-23-3Relevant academic research and scientific papers
Easily synthesizable benzothiazole based designers palladium complexes for catalysis of Suzuki coupling: Controlling effect of aryl substituent of ligand on role and composition of insitu generated binary nanomaterial (PdS or Pd16S7)
Arora, Aayushi,Kumar, Arun,Kumar, Sushil,Oswal, Preeti,Rao, Gyandshwar Kumar,Singh, Ajai K.,Singh, Siddhant
, (2021)
The present report is based on straightforward synthesis of molecular palladium complexes of benzothiazole based bulky ligands. Catalytic potential of 1[Pd(L1)2Cl2] and 2[Pd(L2)2Cl2] has been screened for Suzuki coupling. Due to structural difference between 1 and 2 (anthracen-9-yl in 1, and pyren-1-yl in 2), they behave as designers pre-catalysts and show different catalytic behaviour and nature by dispensing the nanoparticles of different materials (PdS by 1 and Pd16S7 by 2). This is an unprecedented observation as the size of the aryl substituent controls the efficiency (efficiency: 1 > 2) through determining the composition and nature of insitu generated nanoparticles.
Ultrafast Conformational Relaxation Dynamics in Anthryl-9-benzothiazole: Dynamic Planarization Driven Delocalization and Protonation-Induced Twisting Dynamics
Ghosh, Rajib,Nandi, Amitabha,Kushwaha, Archana,Das, Dipanwita
, p. 5307 - 5315 (2019)
Conformational motion in the excited state of fluorophores critically governs their photophysical properties. Unveiling controlling parameters of photoinduced molecular motion in organic dyes is essential for optimization of light-triggered processes. Herein, we present ultrafast dynamics of conformational relaxation controlled photophysical properties of anthryl-9-benzthiazole (AnBT). The title compound is a bichromophore, consists of anthracene (AN) and benzothiazole (BT) units connected by a single bond, and exists in out of plane ground state conformation (dihedral angle of about 65). Vibronic resolved structured absorption feature of anthracene localized excitation is lost in first excited singlet state displaying large Stokes-shifted fluorescence, characteristics of delocalized state involving both AN and BT unit. Ultrafast transient absorption spectroscopic studies revealed evolution of anthracene-localized Franck Condon state to a delocalized excited state in a few picosecond time scale depending on solvent viscosity. A planarized motion of AN and BT units is proposed to be involved in excited state relaxation. However, protonation of BT unit is shown to induce significant intramolecular charge transfer facilitated by ultrafast torsional relaxation promoting nonradiative deactivation. Thus, depending upon protonation state, AnBT is shown to undergo either ultrafast planarized motion facilitating delocalized emissive excited state or perpendicular torsion rendering nonemissive twisted intramolecular charge transfer state. Experimental results were corroborated by quantum chemical calculation.
Compound, luminescent layer host material and organic electroluminescent device
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Paragraph 0129-0131; 0148; 0153; 0165, (2021/01/29)
The present application provides a compound of general formula (I), which can be used in a host material of a light emitting layer. Anthracene and a connecting group in the compound have small sterichindrance and good planarity and and can effectively reduce the driving voltage of an organic light-emitting device, so that by means of the technical scheme, the light-emitting efficiency of the organic light-emitting device and the service life of the organic light-emitting device can be improved when the compound is used as a main material of a light-emitting layer. The invention further provides an organic light-emitting device and a display device containing the compound shown in the general formula (I).
Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions
Abdelrasoul, Amira,Ghorashi, Nadia,Moradi, Reza,Rostami, Amin,Shokri, Zahra
, p. 14254 - 14261 (2020/04/23)
The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O2 as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.
Visible-light-driven synthesis of 2-substituted benzothiazoles using CdS nanosphere as heterogenous recyclable catalyst
Das, Sudipto,Samanta, Suvendu,Maji, Swarup Kumar,Samanta, Partha Kumar,Dutta, Amit Kumar,Srivastava, Divesh N.,Adhikary, Bibhutosh,Biswas, Papu
, p. 1090 - 1096 (2013/05/08)
This Letter reports simple, green, and efficient synthesis of mesoporous CdS nanosphere (CdSNS) and its application as heterogeneous catalyst for the synthesis of 2-substituted benzothiazole. We report, for the first time, the synthesis of 2-substituted benzothiazoles from various aryl and alkyl aldehydes under visible light irradiation at room temperature. CdSNS catalyst generated in water demonstrates excellent catalytic activity for both the alkyl and aryl aldehydes, with good recyclability. The reaction yield is high for the electron-donating and electron withdrawing substituents as well as heterocyclic aldehydes with good turn over number (TON) and turnover frequency (TOF).
Photocatalysis by 3,6-disubstituted-s-tetrazine: Visible-light driven metal-free green synthesis of 2-substituted benzimidazole and benzothiazole
Samanta, Suvendu,Das, Sudipto,Biswas, Papu
, p. 11184 - 11193 (2013/12/04)
s-Tetrazine based molecules were prepared for visible-light-driven organic transformations. The 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) derivative shows visible light absorption and reversible one-electron reduction behavior. In the presence of pytz and aerial oxygen, aldehyde reacts with o-phenylenediamine or o-aminothiophenol under visible light irradiation at ambient temperature to produce corresponding 2-substituted benzimidazoles and benzothiazoles, respectively. Pytz catalyst demonstrates excellent catalytic activity for alkyl, aryl, organo-metallic substituted aldehydes and reducing sugar. The reaction yield is high for both the electron-donating and electron withdrawing substituents in aromatic aldehydes. The use of a metal-free catalyst and visible light energy, along with the mild reaction conditions, makes this reaction an environmentally benign and energy-saving chemical process.
Sulfamic acid as a recyclable and green catalyst for rapid and highly efficient synthesis of 2-arylbenzothiazoles in water at room temperature
Rostami,Yari
, p. 489 - 493 (2013/02/22)
2-Arylbenzothiazoles have been synthesized in water in good to excellent yield from direct condensation of various aromatic aldehydes with 2-aminothiophenol promoted by catalytic amount of sulfamic acid at room temperature. This method provides a simple,
Nickel-catalyzed C-H arylation of azoles with haloarenes: Scope, mechanism, and applications to the synthesis of bioactive molecules
Yamamoto, Takuya,Muto, Kei,Komiyama, Masato,Canivet, Jerome,Yamaguchi, Junichiro,Itami, Kenichiro
supporting information; experimental part, p. 10113 - 10122 (2011/10/08)
Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)2/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)2/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, we discovered a new protocol for the present coupling using Mg(OtBu)2 as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodology has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). Copyright
Novel green procedure for the synthesis of 2-arylbenzothiazoles under microwave irradiation in Peg 200 or Peg 400
Deligeorgiev, Todor G.,Kaloyanova, Stefka,Vasilev, Aleksey,Vaquero, Juan J.
experimental part, p. 2292 - 2302 (2011/01/12)
An improved green procedure for the synthesis of 2-aryl- and 2-hetarylbenzothiazoles by condensation of equivalent amounts of 2,2'-diaminodiphenyldisulfides or 2-aminothiophenols and various aromatic aldehydes in PEG 200/400 under microwave irradiation has been developed. This method allows the synthesis of 2-arylbenzothiazoles in high yields and with high purity regardless of the state of the starting compounds (liquid or solid) or the nature of the substituents in the aromatic ring. Copyright Taylor & Francis Group, LLC.
Photophysics of novel 2,6-disubstituted benzobisthiazoles possessing chromophoric groups
Sasaki, Takashi,Inoue, Takashi,Komori, Yukari,Irie, Satoshi,Sakurai, Kensuke,Tsubakiyama, Kyoji
, p. 1381 - 1385 (2007/10/03)
A series of 2,6-disubstituted benzo[1,2-d:4,5-d′]bisthiazoles that have two photofunctional groups was synthesized, and their absorption and emission spectra in chloroform solution were examined. An anthracene derivative, 2,6-di(9-anthryl)benzo[1,2-d:4,5-d′]bisthiazole (DABBT), as well as a mono-substituted compound, 2-(9-anthryl)benzothiazole (ABT), showed a broad emission band at a long wavelength without any monomer emission of an anthryl group even for a concentration as low as 5 × 10-7 M. In contrast, naphthalene derivatives, 2,6-di(1-naphthyl)benzo[1,2-d:4,5-d′]bisthiazole (D1NBBT) and 2,6-di(2-naphthyl)benzo[1,2-d:4,5-d′]bisthiazole (D2NBBT), showed entirely monomer emission of a naphthyl group with no broad emission band at longer wavelengths. The broad emission bands observed for DABBT and ABT are attributed to an excited charge-transfer state in which an electron has transferred from a benzothiazole unit to an anthryl group.
