867349-79-9Relevant academic research and scientific papers
Effective modulation of the photoluminescence properties of 2,1,3-benzothiadiazoles and 2,1,3-benzoselenadiazoles by Pd-catalyzed C-H bond arylations
Idris, Imane,Tannoux, Thibault,Derridj, Fazia,Dorcet, Vincent,Boixel, Julien,Guerchais, Veronique,Soulé, Jean-Fran?ois,Doucet, Henri
supporting information, p. 1731 - 1737 (2018/02/23)
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.
Photophysical and electrochemical properties of π-extended molecular 2,1,3-benzothiadiazoles
DaSilveira Neto, Brenno A.,Lopes, Aline Sant'Ana,Ebeling, Gunter,Gon?alves, Reinaldo S.,Costa, Valentim E. U.,Quina, Frank H.,Dupont, Jairton
, p. 10975 - 10982 (2007/10/03)
The reaction of 4,7-dibromo-2,1,3-benzothiadiazole with arylboronic acids (phenyl, 1-naphthyl, 4-methoxyphenyl, 4-chlorophenyl and 4- trifluoromethylphenyl) in the presence of catalytic amounts of a NCP-pincer palladacycle affords photoluminescent π-extended 4,7-diaryl-2,1,3- benzothiadiazoles 4a-e in high yields. These 4,7-diaryl-2,1,3-benzothiadiazoles exhibit high fluorescent quantum yields, high electron affinities and adequate band gap values for testing as OLEDs. The 4,7-bis-naphthyl-2,1,3- benzothiadiazole 4b presents two different lifetimes (bi-exponential decay) due to the presence of two atropisomers. The Sonogashira coupling reaction of 4,7-diethynyl-2,1,3-benzothiadiazole 6 with the corresponding halo-aryl compounds (iodobenzene, 1-bromonaphthalene, 4-iodoanisole, 4-bromo-N,N- dimethylaniline and 2-bromopyridine) afforded the photoluminescent π-extended 4,7-bis-alkynylaryl-2,1,3-benzothiadiazoles 7a-e, also in high yields. These 4,7-diethynyl-2,1,3-benzothiadiazoles also present high fluorescent quantum yields, high electron affinities and adequate band gap values for testing as OLEDs. The 4,7-disubstituted-2,1,3-benzothiadiazoles 4a-e and 7a-e exhibit different electrochemical behavior. The presence of two ethynyl spacers in 2,1,3-benzothiadiazoles 7a-e shifts the reduction potentials to less cathodic values and also results in two well-defined and distinct reduction processes.
Reductive sulfur extrusion reaction of 2,1,3-benzothiadiazole compounds: A new methodology using NaBH4/CoCl2·6H 2O(cat) as the reducing system
DaSilveira Neto, Brenno A.,Lopes, Aline S.,Wüst, Martina,Costa, Valentim E. U.,Ebeling, Günter,Dupont, Jairton
, p. 6843 - 6846 (2007/10/03)
A new simple and efficient methodology for reductive sulfur extrusion from 2,1,3-benzothiadiazole compounds has been developed using NaBH4 in the presence of catalytic amounts of CoCl2·6H2O (1 mol %). This method is an efficient alternative for the generation of various 1,4-disubstituted-2,3-diaminobenzene derivatives from 4,7-disubstituted-2,1,3- benzothiadiazoles. The diamines can be easily converted into 4,7-disubstituted-quinoxaline compounds by simple reaction with glyoxal-sodium bisulfite.
