6007-85-8Relevant articles and documents
From-core and from-end direct C-H arylations: A step-saving new synthetic route to thieno[3,4-c]pyrrole-4,6-dione (TPD)-incorporated D-π-A-π-D functional oligoaryls
Lin, Po-Han,Liu, Kuan-Ting,Liu, Ching-Yuan
, p. 8754 - 8757 (2015)
In contrast to the traditional multistep synthesis, herein an efficient and fewer-steps new synthetic strategy is demonstrated for the facile preparation of organic-electronically important D-π-A-π-D-type oligoaryls through sequential direct C-H arylations. This methodology has shown that the synthesis of thieno[3,4-c]pyrrole-4,6-dione (TPD)- or furano[3,4-c]pyrrole-4,6-dione (FPD)-centred target molecules could be accessed step-economically either from the core structure (acceptor) or from the end structure (donor), which supplied a more flexible and succinct new synthetic alternative to the preparation of the π-functional small-molecule semiconducting materials. In addition, optical and electrochemical properties of the synthesized oligoaryls were examined.
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Takaya et al.
, p. 2532 (1968)
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A Distannylated Monomer of a Strong Electron-Accepting Organoboron Building Block: Enabling Acceptor–Acceptor-Type Conjugated Polymers for n-Type Thermoelectric Applications
Deng, Sihui,Dong, Changshuai,Liu, Jun,Meng, Bin,Wang, Lixiang
, p. 16184 - 16190 (2021)
Acceptor–acceptor (A-A) copolymerization is an effective strategy to develop high-performance n-type conjugated polymers. However, the development of A-A type conjugated polymers is challenging due to the synthetic difficulty. Herein, a distannylated monomer of strong electron-deficient double B←N bridged bipyridine (BNBP) unit is readily synthesized and used to develop A-A type conjugated polymers by Stille polycondensation. The resulting polymers show ultralow LUMO energy levels of ?4.4 eV, which is among the lowest value reported for organoboron polymers. After n-doping, the resulting polymers exhibit electric conductivity of 7.8 S cm?1 and power factor of 24.8 μW m?1 K?2. This performance is among the best for n-type polymer thermoelectric materials. These results demonstrate the great potential of A-A type organoboron polymers for high-performance n-type thermoelectrics.
CRYSTAL FORMS OF THIOPHENE DERIVATIVES
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Paragraph 0274, (2021/05/14)
Disclosed is crystal form I of compound (S)—N-[5-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-4,6-dioxo-5,6-dihydro-4H-thieno[3,4-c]pyrrole-1-yl]acetamide.
From Red to Green Luminescence via Surface Functionalization. Effect of 2-(5-Mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4- c]pyrrole-4,6-dione Ligands on the Photoluminescence of Alloyed Ag-In-Zn-S Nanocrystals
Kowalik, Patrycja,Bujak, Piotr,Wróbel, Zbigniew,Penkala, Mateusz,Kotwica, Kamil,Maroń, Anna,Pron, Adam
supporting information, p. 14594 - 14604 (2020/10/09)
A semiconducting molecule containing a thiol anchor group, namely 2-(5-mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4-c]pyrrole-4,6-dione (abbreviated as D-A-D-SH), was designed, synthesized, and used as a ligand in nonstoichiometric quaternary nanocrystals of composition Ag1.0In3.1Zn1.0S4.0(S6.1) to give an inorganic/organic hybrid. Detailed NMR studies indicate that D-A-D-SH ligands are present in two coordination spheres in the organic part of the hybrid: (i) inner in which the ligand molecules form direct bonds with the nanocrystal surface and (ii) outer in which the ligand molecules do not form direct bonds with the inorganic core. Exchange of the initial ligands (stearic acid and 1-aminooctadecane) for D-A-D-SH induces a distinct change of the photoluminescence. Efficient red luminescence of nanocrystals capped with initial ligands (λmax = 720 nm, quantum yield = 67%) is totally quenched and green luminescence characteristic of the ligand appears (λmax = 508 nm, quantum yield = 10%). This change of the photoluminescence mechanism can be clarified by a combination of electrochemical and spectroscopic investigations. It can be demonstrated by cyclic voltammetry that new states appear in the hybrid as a consequence of D-A-D-SH binding to the nanocrystals surface. These states are located below the nanocrystal LUMO and above its HOMO, respectively. They are concurrent to deeper donor and acceptor states governing the red luminescence. As a result, energy transfer from the nanocrystal HOMO and LUMO levels to the ligand states takes place, leading to effective quenching of the red luminescence and appearance of the green one.
