110851-65-5Relevant articles and documents
Novel s-tetrazine-based dyes with enhanced two-photon absorption cross-section
Quinton, Cassandre,Chi, San-Hui,Dumas-Verdes, Ccile,Audebert, Pierre,Clavier, Gilles,Perry, Joseph W.,Alain-Rizzo, Valrie
, p. 8351 - 8357 (2015)
This paper reports the synthesis and the linear and non-linear absorption properties of a series of new tetrazine-based D-π-A-π-D and D-π-A type dyes. In these derivatives, a central tetrazine core was connected with one or two terminal triphenylamine moi
Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells
Dutta, Pranabesh,Yang, Wooseung,Eom, Seung Hun,Lee, Soo-Hyoung
, p. 273 - 282 (2012)
Two new small molecules, 5,5-bis(2-triphenylamino-3-decylthiophen-2-yl)-2, 2-bithiazole (M1) and 2,5-bis(2-triphenylamino-3-decylthiophen-2-yl)thiazolo[5, 4-d]thiazole (M2) based on an electron-donor triphenylamine unit and electron-acceptor thiophene-thiazolothiazole or thiophene-bithiazole units were synthesized by a palladium(0)-catalyzed Suzuki coupling reaction and examined as donor materials for application in organic solar cells. The small molecules had an absorption band in the range of 300-560 nm, with an optical band gap of 2.22 and 2.25 for M1 and M2, respectively. As determined by cyclic voltammetry, the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of M1 were -5.27 eV and -3.05 eV, respectively, which were 0.05 eV and 0.02 eV greater than that of M2. Photovoltaic properties of the small molecules were investigated by constructing bulk-heterojunction organic solar cell (OSC) devices using M1 and M2 as donors and fullerene derivatives, 6,6-phenyl-C61-butyric acid methyl ester (PC61BM) and 6,6-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptors with the device architecture ITO/PEDOT:PSS/M1 or M2:PCBM/LiF/Al. The effect of the small molecule/fullerene weight ratio, active layer thickness, and processing solvent were carefully investigated to improve the performance of the OSCs. Under AM 1.5 G 100 mW/cm2 illumination, the optimized OSC device with M1 and PC71BM at a weight ratio of 1:3 delivered a power conversion efficiency (PCE) of 1.30%, with a short circuit current of 4.63 mA/cm 2, an open circuit voltage of 0.97 V, and a fill factor of 0.29. In contrast, M2 produced a better performance under identical device conditions. A PCE as high as 2.39% was recorded, with a short circuit current of 6.49 mA/cm2, an open circuit voltage of 0.94 V, and a fill factor of 0.39.
Cobalt-Catalyzed Reductive Alkylation of Heteroaryl Bromides: One-Pot Access to Alkylthiophenes, -furans, -selenophenes, and -pyrroles
Cai, Deng-Jhou,Lin, Po-Han,Liu, Ching-Yuan
, p. 5448 - 5452 (2015/08/24)
A practical and convenient Co-catalyzed alkylation method for the facile introduction of various alkyl chains into organic electronically significant heteroaryl compounds, including thiophenes, furans, selenophenes, and pyrroles, is reported. Under well-optimized reaction conditions, a wide range of alkylated heteroaryl compounds have beeen efficiently prepared in moderate to good isolated yields. Notably, 2- or 3-alkylthiophenes, which play a decisive role in polymer chemistry and organic materials, have been synthesized step-economically for the first time by this reductive-coupling methodology using inexpensive cobalt salts as catalysts. This straightforward synthetic procedure avoids the preparation of moisture-unstable organometallic reagents (RMgX or RZnX) required in conventional alkylation protocols. Various alkyl chains have been introduced into organic, electronically important heteroaryl compounds step-economically through Co-catalyzed reductive alkylation reactions. The resulting alkylheteroarenes are indispensable building blocks for polymer chemistry and π-functional organic materials.
Triphenylamine/tetrazine based π-conjugated systems as molecular donors for organic solar cells
Quinton, Cassandre,Alain-Rizzo, Valérie,Dumas-Verdes, Cécile,Clavier, Gilles,Vignau, Laurence,Audebert, Pierre
, p. 9700 - 9713 (2015/12/01)
Conjugated systems built by connecting one electron-donor triphenylamine to an electron-withdrawing tetrazine have been prepared using various linkers. We describe here the synthesis, the electrochemical properties and some photophysical properties of the
