Abstract:Thiadiazole derivatives R 0300Photophysical and Electrochemical Properties of π-Extended Molecular 2,1,3-Benzothiadiazoles. -Suzuki and Sonogashira cross coupling reactions are used to prepare 4,7-disubstituted 2,1,3-benzothiadiazoles with extended π-system (III) and (VI). These compounds show interesting photo-luminescent and photo-electronic properties which make them promising candidates for testing as organic LED's. -(DASILVEIRA NETO, B. A.; LOPES, A. S.; EBELING, G.; GONCALVES, R. S.; COSTA, V. E. U.; QUI… Show more
“…The synthesis of dibromobenzothiadiazole is outlined in Scheme 1 . The reaction of 1 with molecular bromine (added dropwise very slowly) in hydrobromic acid exclusively affords 4,7-dibromobenzothiadiazole ( 2 ) as a major product in 95% yield (Scheme 1 ) [ 7 ]. Scheme 1 Synthesis of dibromobenzothiadiazole …”
The benzothiadiazole – arylene alternating conjugated oligomers have been designed and synthesized via Suzuki coupling reaction. The structures and properties of the conjugated oligomers were characterized by 1HNMR, 13CNMR, UV–vis absorption spectroscopy, photoluminescence (PL) spectroscopy. The luminescent measurements demonstrate that polybenzothiadiazoles are good chromophores able to form thin films by Langmuir-Blodgett (LB) technique, making them suitable for further applications. Also the electrical properties of obtained films confirm the good potential of these novel aryl-based π-conjugated polymers for the development of various electrical and electrochemical solid-state devices.
“…The synthesis of dibromobenzothiadiazole is outlined in Scheme 1 . The reaction of 1 with molecular bromine (added dropwise very slowly) in hydrobromic acid exclusively affords 4,7-dibromobenzothiadiazole ( 2 ) as a major product in 95% yield (Scheme 1 ) [ 7 ]. Scheme 1 Synthesis of dibromobenzothiadiazole …”
The benzothiadiazole – arylene alternating conjugated oligomers have been designed and synthesized via Suzuki coupling reaction. The structures and properties of the conjugated oligomers were characterized by 1HNMR, 13CNMR, UV–vis absorption spectroscopy, photoluminescence (PL) spectroscopy. The luminescent measurements demonstrate that polybenzothiadiazoles are good chromophores able to form thin films by Langmuir-Blodgett (LB) technique, making them suitable for further applications. Also the electrical properties of obtained films confirm the good potential of these novel aryl-based π-conjugated polymers for the development of various electrical and electrochemical solid-state devices.
“…Simply because there are no hydrogen atoms present within the 1,2,5-thiadiazole 1,1-dioxide moiety, the 1 H NMR spectra are useless when it comes to the structural characterization of this class of compounds. Several 13 C NMR spectra have been reported for 3,4-disubstituted derivatives; carbon signals originating from 1,2,5-thiadiazole 1,1-dioxide ring appear in the 150–170 ppm range [ 59 , 60 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ] as compared to the 130–160 ppm range for 1,2,5-thiadiazoles [ 69 , 70 , 71 ]. Many compounds were not characterized by 13 C NMR spectroscopy due to their relatively low solubility in common deuterated solvents [ 43 , 45 , 51 , 67 ].…”
This work provides a summary of the preparation, structure, reactivity, physicochemical properties, and main uses of 1,2,5-thiadiazole 1,1-dioxides in chemistry and material sciences. An overview of all currently known structures containing the 1,2,5-thiadiazole 1,1-dioxide motif (including the anions radical species) is provided according to the Cambridge Structural Database search. The analysis of the bond lengths typical for neutral and anion radical species is performed, providing a useful tool for unambiguous assessment of the valence state of the dioxothiadiazole-based compounds based solely on the structural data. Theoretical methodologies used in the literature to describe the dioxothiadiazoles are also shortly discussed, together with the typical ‘fingerprint’ of the dioxothiadiazole ring reported by means of various spectroscopic techniques (NMR, IR, UV-Vis). The second part describes the synthetic strategies leading to 1,2,5-thiadiazole 1,1-dioxides followed by the discussion of their electrochemistry and reactivity including mainly the chemical methods for the successful reduction of dioxothiadiazoles to their anion radical forms and the ability to form coordination compounds. Finally, the magnetic properties of dioxothiadiazole radical anions and the metal complexes involving dioxothiadiazoles as ligands are discussed, including simple alkali metal salts and d-block coordination compounds. The last section is a prospect of other uses of dioxothiadiazole-containing molecules reported in the literature followed by the perspectives and possible future research directions involving these compounds.
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