883742-29-8Relevant articles and documents
Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives
Britton, Luke,Skrodzki, Maciej,Nichol, Gary S.,Dominey, Andrew P.,Pawlu?, Piotr,Docherty, Jamie H.,Thomas, Stephen P.
, p. 6857 - 6864 (2021/06/28)
Aryl boronic esters are bench-stable, platform building-blocks that can be accessed through metal-catalyzed aryl C(sp2)-H borylation reactions. C(sp2)-H bond functionalization reactions using rare- and precious-metal catalysts are well established, and while examples utilizing Earth-abundant alternatives have emerged, manganese catalysis remains lacking. The manganese-catalyzed C-H borylation of furan and thiophene derivatives is reported alongside an in situ activation method providing facile access to the active manganese hydride species. Mechanistic investigations showed that blue light irradiation directly affected catalysis by action at the metal center, that C(sp2)-H bond borylation occurs through a C-H metallation pathway, and that the reversible coordination of pinacolborane to the catalyst gave a manganese borohydride complex, which was as an off-cycle resting state.
C-H Borylation Catalysis of Heteroaromatics by a Rhenium Boryl Polyhydride
Donnelly, Liam J.,Faber, Teresa,Morrison, Carole A.,Nichol, Gary S.,Thomas, Stephen P.,Love, Jason B.
, p. 7394 - 7400 (2021/06/30)
Transition metal complexes bearing metal-boron bonds are of particular relevance to catalytic C-H borylation reactions, with iridium polyboryl and polyhydrido-boryl complexes the current benchmark catalysts for these transformations. Herein, we demonstrate that polyhydride boryl phosphine rhenium complexes are accessible and catalyze the C-H borylation of heteroaromatic substrates. Reaction of [K(DME)(18-c-6)][ReH4(Bpin)(ν2-HBpin)(κ2-H2Bpin)] 1 with 1,3-bis(diphenylphosphino)propane (dppp) produced [K(18-c-6)][ReH4(ν2-HBpin)(dppp)] 2 through substitution of two equivalents of HBpin, and protonation of 2 formed the neutral complex [ReH6(Bpin)(dppp)] 3. Combined X-ray crystallographic and DFT studies show that 2 is best described as a σ-borane complex, whereas 3 is a boryl complex. Significantly, the boryl complex 3 acted as a catalyst for the C(sp2)-H borylation of a variety of heteroarenes (14 examples including furan, thiophene, pyrrole and indole derivatives) and displayed similar reactivity to the iridium analogues.
Dibenzothiophene pyrrole functional dye containing phenoxy long carbon chain and application thereof (by machine translation)
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Paragraph 0014, (2020/07/02)
The invention discloses a dibenzothiophene pyrrole functional dye containing a phenoxy long carbon chain and an application thereof, and belongs to the technical field of fine chemical engineering and photoelectric chemical materials. The structure of the
A study of oligothiophene-acceptor dyes in p-type dye-sensitized solar cells
Sheibani, Esmaeil,Zhang, Lei,Liu, Peng,Xu, Bo,Mijangos, Edgar,Boschloo, Gerrit,Hagfeldt, Anders,Hammarstr?m, Leif,Kloo, Lars,Tian, Haining
, p. 18165 - 18177 (2016/02/27)
Two new dyes, E1 and E2, equipped with triphenylamine as the electron donor, oligothiophene as the linker and different electron acceptor groups, have been designed and synthesized as photosensitizers for p-type dye-sensitized solar cells (p-DSCs). A systematic study of the effect of molecular structures on the observed photophysical properties, the electron/hole recombination process, the overall performance and the interfacial charge separation was carried out. Transient absorption spectroscopy (TAS) shows that the E1 dye with a napthoilene-1,2-benzimidazole (NBI) unit as the acceptor has a longer lifetime in the reduced state than the E2 dye with a malononitrile subunit on the NiO surface.
Solution processed bulk heterojunction solar cells based on A-D-A small molecules with a dihydroindoloindole (DINI) central donor and different acceptor end groups
Sim, Jangkeun,Lee, Hyejeoung,Song, Kihyoung,Biswas, Subhayan,Sharma, Abhishek,Sharma, Ganesh D.,Ko, Jaejung
supporting information, p. 3508 - 3516 (2016/05/19)
Four acceptor-donor-acceptor (A-D-A) small molecules with dihydroindoloindole (DINI) as the central donor unit and different acceptor end groups such as dicyanovinylene (DCV), indenedione (IND), cyanoacrylate (CA) and rhodanine (Rho) linked through bithiophene as the π-linker, DINI-DCV, DINI-IND, DINI-CA and DINI-Rho, were designed and synthesized for the application as donor materials along with PC71BM as an acceptor for solution processed organic bulk heterojunction solar cells. The effect of acceptor end groups on the photovoltaic performance was investigated. The organic solar cells (OSCs) based on as cast DINI-IND showed the highest power conversion efficiency of 3.04%, as cast DINI-CA showed the lowest PCE of 1.63% and the other two exhibit a PCE in between them. These results showed that acceptor end groups affect the overall performance of the cells. The PCE of OSCs has been further improved up to 7.04% and 6.16% employing two-step annealing (TSA) treated DIN-IND:PC71BM (1:2) and DIN-CN:PC71BM (1:2), respectively. The enhancement in the PCE of OSCs with TSA treated active layers is attributed to the better nanophase morphology, the increase in the crystalline nature and light harvesting efficiency and more balanced charge transport and charge collection probability.
Photophysics and Nonlinear Absorption of Gold(I) and Platinum(II) Donor-Acceptor-Donor Chromophores
Goswami, Subhadip,Winkel, Russell W.,Schanze, Kirk S.
supporting information, p. 10007 - 10014 (2015/11/09)
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
White Electroluminescence with Simultaneous Three-Color Emission from a Four-Armed Star-Shaped Single-Polymer System
Jiu, Yuanda,Wang, Jianyun,Liu, Chengfang,Lai, Wenyong,Zhao, Lingling,Li, Xiangchun,Jiang, Yi,Xu, Weidong,Zhang, Xinwen,Huang, Wei
supporting information, p. 873 - 880 (2015/09/01)
A four-armed star-shaped single-polymer system with 4,7-bis(5-(4-(9H-carbazol-9-yl)phenyl)-4-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (FTBT) as a red emissive core, polyfluorene (PF) as blue emissive arms and 1,3-benzo thiadiazole (BT) as green emissive dopants was designed and synthesized, in which red, green, and blue (RGB) emission balance can be achieved by adjusting the doping concentration of FTBT and BT discreetly. A typical single-emissive-layer device (ITO/PEDOT:PSS/polymer/TPBI/LiF/Al) was studied and discussed, realizing a pure and stable white emission with a luminous efficiency (LE) of 1.59 cd·A-1 and CIE coordinates of (0.31, 0.34). The high-color-quality white electroluminescence of the devices could be mainly attributed to the suppressed intermolecular interactions, and partial energy transfer from the blue PF arms to the red and green dopants. A four-armed star-shaped single-polymer system with simultaneous red, green, and blue (RGB) emission was designed and synthesized, which realized pure and stable white emission with a luminous efficiency (LE) of 1.59 cd·A-1 and CIE coordinates of (0.31, 0.34) in a typical single-emissive-layer device.
Continuous flow synthesis of organic electronic materials-case studies in methodology translation and scale-up
Seyler, Helga,Haid, Stefan,Kwon, Tae-Hyuk,Jones, David J.,Baeuerle, Peter,Holmes, Andrew B.,Wong, Wallace W. H.
, p. 151 - 156 (2013/04/10)
The continuous flow synthesis of functional thiophene derivatives was examined. Methodology for the lithiation of thiophene building blocks was developed using a commercial bench-top flow reactor. In addition, the advantages of flow processing were demonstrated in the synthesis of a high performance organic dye in gram scale.
Concise synthesis of well-defined linear and branched oligothiophenes with nickel-catalyzed regiocontrolled cross-coupling of 3-substituted thiophenes by catalytically generated magnesium amide
Tanaka, Shota,Tanaka, Daiki,Tatsuta, Go,Murakami, Kohei,Tamba, Shunsuke,Sugie, Atsushi,Mori, Atsunori
supporting information, p. 1658 - 1665 (2013/02/25)
The synthesis of linear and branched oligothiophenes of well-defined structures is performed with regioselective deprotonation of 3-substituted thiophenes and nickel-catalyzed cross-coupling of the thus formed metalated species with a bromothiophene. The reaction of 3-hexylthiophene with EtMgCl and 2,2,6,6-tetramethylpiperidine (TMP-H, 10 mol %) induces the metalation selectively at the 5-position by use of the catalytically generated hindered magnesium amide (TMPMgCl) and the subsequent reaction of a 2-halo-3- hexylthiophene (bromide or chloride) in the presence of a nickel catalyst affords a head-to-tail (HT)-type dimer. By repeating the same sequence, the linear oligothiophene up to a 4-mer is synthesized in good yield. The reaction of 3-hexylthiophene with 2,3-dibromothiophene also takes place to afford a branched oligothiophene 3-mer in quantitative yield. The obtained 3-mer is also metalated at the sterically less-hindered position in a regioselective manner furnishing a 7-mer in >99 % yield after a further coupling reaction with 2,3-dibromothiophene. These dendrimers react with several multifunctionalized organic electrophiles, leading to a variety of branched oligothiophenes. Copyright
Tuning band structures of dyes for dye-sensitized solar cells: Effect of different π-bridges on the performance of cells
Liu, Jing,Yang, Xichuan,Zhao, Jinxia,Sun, Licheng
, p. 15734 - 15743 (2013/09/12)
Three organic dyes (LJ101, LJ102, and LJ103) with different π-bridges such as thiophene, 3-hexylthiophene and 3, 4-ethyldioxythiophene, were prepared and applied for the dye-sensitized solar cells (DSSCs). The effect of the different π-bridges on the phot
