Benzothiadiazole Unit (benzothiadiazole + unit)

Distribution by Scientific Domains

Selected Abstracts

Bisthienylethenes Containing a Benzothiadiazole Unit as a Bridge: Photochromic Performance Dependence on Substitution Position

Weihong Zhu Prof.
Abstract A conveniently synthesized photochromic compound, BTB-1, containing an unprecedented six-membered 2,1,3-benzothiadiazole unit as the center ethene bridge, possesses good photochromic performance, with a high cyclization quantum yield and moderate fatigue resistance in solution or an organogel system. The fluorescence of BTB-1 can be modulated by solvato- and photochromism. However, the analogue BTB-2, in which the dimethylthiophene substituents are relocated to the 5,6-positions of benzothiadiazole, does not show any detectable photochromism. To the best of our knowledge, this is the first example of six-membered bridge bisthienylethenes (BTEs) in which the photochromism can be controlled by the substitution position. The photochromism difference is elucidated by the analysis of resonance structure, the Woodward,Hoffmann rule, and theoretical calculations on the ground-state potential-energy surface. In a well-ordered single-crystal state, BTB-1 adopts a relatively rare parallel conformation, and forms an interesting two-dimensional structure due to the presence of multiple directional intermolecular interactions, including CH,,,N and CH,,,S hydrogen-bonding interactions, and ,,, stacking interactions. This work contributes to several aspects for developing novel photochromic BTE systems with fluorescence modulation and performances controlled by substitution position in different states (solution, organogel, and single crystal). [source]

Alkyl side chain driven tunable red,yellow,green emission: Investigation on the new ,-conjugated polymers comprising of 2,7-carbazole unit and 2,1,3-benzo-thiadiazole units with different side chains

Junping Du
Abstract Four new soluble polymers containing a 2,7-carbazole unit and a 2,1,3-benzothiadiazole unit in the main chain were synthesized by Suzuki polycondensation. Variation of the substituent groups (R) at 5-position of 2,1,3-benzothiadiazole unit resulted in different color emission of the copolymers. Thus, when R was CH3 (or H), the polymer showed yellow,green (or red) emission; whereas the polymers showed the emission from green to yellow,green, when R was CH2(CH2)5CH3 or CH2OCH(CH3)2. To investigate the nature of the color change, a Gaussian 03 program was used for estimation of the dihedral angles between a 5-R-2,1,3-benzothiadiazole unit and a 2,7-carbazole unit. The results showed that the different substituents at 5-position of 2,1,3-benzothiadiazole brought about different the dihedral angles, which gave the different conjugation levels to the polymers. Hence, the tunablity of emission color may be attributed to the different conjugation levels between 2,7-carbazole units and 5-R-2,1,3-benzothiadiazole units induced by simply changing substituent groups at 5-position of benzothiadiazole unit. Electrochemically, the copolymers exhibited a higher oxidation potential as well as the reversible reduction behavior bearing from 2,1,3-benzothiadiazole unit. To investigate the electroluminescent properties of the polymers, the nonoptimized devices were fabricated and the results showed that the electroluminescent emission wavelength was basically similar to that of the photoluminescent. All polymers showed good thermal stability with 5 wt % loss temperature of more than 296 C. 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 1376,1387, 2008 [source]

Improved EL efficiency of fluorene-thieno[3,2- b]thiophene-based conjugated copolymers with hole-transporting or electron-transporting units in the main chain

Eunhee Lim
Abstract New electroluminescent polymers (poly(9,9,-dioctylfluorene- co -thieno[3,2- b]thiophene- co -benzo[2,3,5]thiadiazole) (P1) and poly(9,9,-dioctylfluorene- co -thieno[3,2- b]thiophene- co -benzo[2,3,5]thiadiazole- co -[4-(2-ethylhexyloxyl)phenyl]diphenylamine (P2)) possess hole-transporting or electron-transporting units or both in the main chains. Electron-deficient benzothiadiazole and electron-rich triphenylamine moieties were incorporated into the polymer backbone to improve the electron-transporting and hole-transporting characteristics, respectively. P1 and P2 show greater solubility than poly(9,9,-dioctylfluorene- co -thieno[3,2- b]thiophene (PFTT), without sacrificing their good thermal stability. Moreover, owing to the incorporation of the electron-deficient benzothiadiazole unit, P1 and P2 exhibit remarkably lower LUMO levels than PFTT, and thus, it should facilitate the electron injection into the polymer layer from the cathode electrode. Consequently, because of the balance of charge mobility, LED devices based on P1 and P2 exhibit greater brightness and efficiency (up to 3000 cd/m2 and 1.35 cd/A) than devices that use the pristine PFTT. 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 243,253, 2006 [source]

Low Bandgap Polymers by Copolymerization of Thiophene with Benzothiadiazole

Youjun He
Abstract Three low bandgap copolymers of thiophene and benzothiadiazole with electron-donating and electron-withdrawing substituents, P1, P2, and P3, have been synthesized by Pd-catalyzed Stille-coupling. Electronic energy levels of the polymers are estimated by cyclic voltammetry. The polymer films show a broad absorption band in the wavelength range from 300 to 750 nm. Among the polymers, the polymer that contains the 5,6-dinitrobenzothiadiazole unit, P3, possesses the smallest bandgap of 1.55 eV calculated from its absorption band-edge at ,800 nm. With the increase of the electron-withdrawing ability of the substituents on the benzothiadiazole unit, the energy bandgap of the polymers decreased in the order P1,>,P2,>,P3. The results indicate that stronger electron-withdrawing substituents on the acceptor unit can effectively decrease the bandgap of the polymers. [source]