761416-46-0Relevant articles and documents
Synthesis and applications of main-chain Ru(ii) metallo-polymers containing bis-terpyridyl ligands with various benzodiazole cores for solar cells
Padhy, Harihara,Sahu, Duryodhan,Chiang, I-Hung,Patra, Dhananjaya,Kekuda, Dhananjay,Chu, Chih-Wei,Lin, Hong-Cheu
, p. 1196 - 1205 (2011)
A series of π-conjugated bis-terpyridyl ligands (M1-M3) bearing various benzodiazole cores and their corresponding main-chain Ru(ii) metallo-polymers were designed and synthesized. The formation of metallo-polymers were confirmed by NMR, relative viscosity, and UV-visible titration measurements. The effects of electron donor and acceptor interactions on their thermal, optical, electrochemical, and photovoltaic properties were investigated. Due to the strong intramolecular charge transfer (ICT) interaction and metal to ligand charge transfer (MLCT) in Ru(ii)-containing polymers, the absorption spectra covered a broad range of 260-750 nm with the optical band gaps of 1.77-1.63 eV. In addition, due to the broad sensitization areas of the metallo-polymers, their bulk heterojunction (BHJ) solar cell devices containing [6,6]-phenyl-C 61-butyric acid methyl ester (PCBM) as an electron acceptor exhibited a high short-circuit current (Jsc). An optimum PVC device based on the blended polymer P1:PCBM = 1:1 (w/w) achieved the maximum power conversion efficiency (PCE) value up to 0.45%, with Voc = 0.61 V, Jsc = 2.18 mA cm-2, and FF = 34.1% (under AM 1.5 G 100 mW cm -2), which demonstrated a novel family of conjugated polyelectrolytes with the highest PCE value comparable with BHJ solar cells fabricated from ionic polythiophene and C60.
Photophysics and Nonlinear Absorption of Gold(I) and Platinum(II) Donor-Acceptor-Donor Chromophores
Goswami, Subhadip,Winkel, Russell W.,Schanze, Kirk S.
, p. 10007 - 10014 (2015)
A series of Au(I) and Pt(II) acetylide complexes of a -conjugated donor-acceptor-donor (D-A-D) chromophore were studied to develop quantitative structure-property relationships for their photophysical and nonlinear optical properties. The D-A-D chromophor
Synthesis and electroluminescent properties of high-efficiency saturated red emitter based on copolymers from fluorene and 4,7-Di(4-hexylthien-2-yl)-2,1, 3-benzothiadiazole
Hou, Qiong,Zhou, Qingmei,Zhang, Yong,Yang, Wei,Yang, Renqiang,Cao, Yong
, p. 6299 - 6305 (2004)
Novel soluble conjugated random copolymers are synthesized by palladium-catalyzed Suzuki coupling reaction from 9,9-dioctylfluorene (DOF) and 4,7-di(4-hexylthien-2-yl)-2,1,3-benzothiadiazole (DHTBT) with DHTBT composition varying from 1 to 50 mol % in the copolymer. All of the polymers are soluble in common organic solvents and are highly photoluminescent. Polyfluorene fluorescence is quenched completely at a DHTBT concentration as low as 1% in the solid film. The copolymer films are highly fluorescent under UV irradiation in contrast to its parent analogue, 4,7-di(thien-2-yl)-2,1,3-benzothiadiazole (PFO-DBT), without alkyl substitution on thiophene rings. Devices made up of these copolymers emit saturated red light. The emission peaks are shifted from 613 to 672 nm when the DHTBT content increases from 1 to 50%. The highest external quantum efficiency achieved in the device configuration ITO/PEDT/PVK/PFO-DHTBT/Ba/Al is 2.54% with luminous efficiency 1.45 cd/A for the copolymer with emission peak at 638 nm for 10% DHTBT content, among the highest values so far reported for saturated red polymer emitters.
Synthesis and superior optical-limiting properties of fluorene-thiophene- benzothiadazole polymer-functionalized graphene sheets
Midya, Anupam,Mamidala, Venkatesh,Yang, Jia-Xiang,Ang, Priscilla Kai Lian,Chen, Zhi-Kuan,Ji, Wei,Loh, Kian Ping
, p. 2292 - 2300 (2010)
A polymer based on fluorene, thiophene, and benzothiadazole as the donor-spacer-acceptor triad is covalently coupled to reduced graphene oxide (rGO) sheets via diazonium coupling with phenyl bromide, followed by Suzuki coupling. These polymer-graphene hybrids show good solubility in organic solvents, such as chloroform, tetrahydrofuran (THF), toluene, dichlorobenzene, and N,N-dimethylformamide (DMF), and exhibit an excellent optical-limiting effect with a 532-nm laser beam. The optical-limiting threshold energy values (0.93 J cm2 for G-polymer 1 and 1.12 J cm2 for G-polymer 2) of these G-polymer hybrids are better than that of carbon nanotubes (3.6 J cm2). Copyright 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
N-Phenylcarbazole substituted bis(hexylthiophen-2-yl)-benzothiadiazoles as deep red emitters for hole-transporting layer free solution-processed OLEDs
Chaiwai, Chaiyon,Chasing, Pongsakorn,Kaewpuang, Terdkait,Manyum, Thanaporn,Namuangruk, Supawadee,Promarak, Vinich,Sudyoadsuk, Taweesak,Wongkaew, Paweena
, (2021)
Two structural isomers of donor-π-acceptor-π-donor (D-π-A-π-D) type red light-emitting molecules (C3TBz and C4TBz), comprising N-phenylcarbazole as a donor, 2,1,3-benzothiadiazole as an acceptor, and either 3-hexylthiophene or 4-hexylthiophene as π-linkages, respectively, were designed and synthesized as hole-transporting emissive materials for OLEDs. C3TBz and C4TBz were chemically characterized, and their photoelectric properties were investigated by spectroscopy, electrochemical and theoretical studies. They showed strong D-A characteristics with intense deep red fluorescence in solutions, decent hole-transporting ability, good thermal and electrochemical stabilities. Both materials were successfully employed as emitters in the solution-processed double-layered OLEDs, which resulted in a pure red emission with promising device performance. Notably, the C3TBz-based device reached the best EL results with a maximum brightness of 2557 cd m?2, a maximum EQE of 3.08%, a maximum luminance efficiency of 4.87 cd A?1, and a low turn-on voltage of 3.2 V.
MLCT based colorimetric probe for iron having D-A-D type architecture of benzo[2,1,3]thiadiazole acceptor and thiophene donor with azomethine pendant arm
Pati, Palas Baran,Zade, Sanjio S.
, p. 114 - 118 (2014)
A new chemosensor 3 having D-A-D type architecture of benzo[2,1,3] thiadiazole acceptor and thiophene donor with azomethine pendant arm was synthesized and its metal recognition capability was studied over the first row transition metal series. Compound 3 showed colorimetric sensitivity and selectivity towards for Fe(II) and Fe(III). Change in the strength of intramolecular charge transfer (ICT) due to metal to ligand charge transfer (MLCT) is responsible for color change. It has been established using CV and NMR titration. The sensitivity of 3 is in the range of μM concentration that leads to the visual detection by changing color from yellow to orange.
Highly fluorescent solid-state benzothiadiazole derivatives as saturated red emitters for efficient solution-processed non-doped electroluminescent devices
Chaiwai, Chaiyon,Chasing, Pongsakorn,Chawanpunyawat, Thanyarat,Kaewpuang, Terdkait,Manyum, Thanaporn,Namuangruk, Supawadee,Promarak, Vinich,Sudyoadsuk, Taweesak
, p. 10464 - 10473 (2020)
Four donor-π-acceptor type saturated red emitters, namely BTZn, employing two isomeric bis(n-hexylthiophen-2-yl)-benzothiadiazoles as the π-acceptor core and a triphenylamine donor as multiple substituents, were designed and synthesized. The highly twiste
Synthesis and photovoltaic properties of amorphous polymers based on dithienylbenzothiadiazole-triphenylamine with hexyl side chains on different positions of thienyl groups
Yasuda, Takeshi,Shinohara, Yuki,Matsuda, Takaaki,Han, Liyuan,Ishi-I, Tsutomu
, p. 2536 - 2544 (2013)
We synthesized and characterized three new amorphous dithienylbenzothiadiazole (TBT)-triphenylamine (TPA) polymers for application in bulk-heterojunction (BHJ) organic photovoltaic (OPV) cells. Poly(3HTBT-TPA) has hexyl side chains on the thienyl groups (pointing toward the benzothiadiazole (BTD) unit), and poly(4HTBT-TPA) has hexyl side chains on the thienyl groups (pointing outward from the BTD unit). The incident photon to current conversion efficiencies (IPCEs) in the region from 550 to 650 nm for the OPV cells prepared using poly(4HTBT-TPA) were higher than those for the OPV cells prepared using poly(3HTBT-TPA) because the absorption spectrum for the poly(4HTBT-TPA) has a slightly red-shifted absorption edge. We also demonstrated that the poly(4HTBT-TPA)-based OPV performance is independent of the fabrication process, so using an amorphous film to fabricate BHJ OPV cells offers great advantages over using a polycrystalline film in terms of the high reproducibility of the OPV performance.
Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications
Aslan, Sultan Taskaya,Cevher, Duygu,Bolay?r, Eda,Hizalan Ozsoy, Gonul,Arslan Udum, Yasemin,Y?ld?r?m, Erol,Toppare, Levent,Cirpan, Ali
, (2021/10/05)
A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were performed on model tetramer structures to shed light on how substituting the fluorine atom to the acceptor building block affects the structural, electronic and optical properties of the polymers. The results of computational studies were compared with experimental studies. The structure adjustment accomplished by fluorine substitution on the benzothiadiazole moiety reveals an influence on the electronic structure of polymers with a more negative HOMO energy level. A high VOC for the resulting photovoltaic device was examined for PBDTSe-FFBT. Difluorinated polymer PBDTSe-FFBT:PC71BM organic solar cell exhibited the highest photovoltaic performance of 2.63% with JSC of 7.24 mA cm-2, VOC of 0.72 V and FF of 50.6%. PBDTSe-BT:PC71BM revealed the best PCE as 2.39%, and the device reached the highest efficiency up to 1.68% for PBDTSe-FBT:PC71BM.
High efficiency and low efficiency roll-off hole-transporting layer-free solution-processed fluorescent NIR-OLEDs based on oligothiophene-benzothiadiazole derivatives
Chaiwai, Chaiyon,Chasing, Pongsakorn,Kaewpuang, Terdkait,Manyum, Thanaporn,Namuangruk, Supawadee,Promarak, Vinich,Sudyoadsuk, Taweesak
supporting information, p. 5045 - 5050 (2020/04/28)
We report on simple low band-gap D-A-D type chromophores comprising triphylamine as a donor and oligothiophene-benzothiadiazoles as an acceptor. In the solid state, they exhibited strong near-infrared (NIR) emission with high fluorescence quantum yield wh
