7333-08-6Relevant articles and documents
Inhibition of carboxylesterases by benzil (diphenylethane-1,2-dione) and heterocyclic analogues is dependent upon the aromaticity of the ring and the flexibility of the dione moiety
Hyatt, Janice L.,Stacy, Vanessa,Wadkins, Randy M.,Yoon, Kyoung Jin P.,Wierdl, Monika,Edwards, Carol C.,Zeller, Matthias,Hunter, Allen D.,Danks, Mary K.,Crundwell, Guy,Potter, Philip M.
, p. 5543 - 5550 (2005)
Benzil has been identified as a potent selective inhibitor of carboxylesterases (CEs). Essential components of the molecule required for inhibitory activity include the dione moiety and the benzene rings, and substitution within the rings affords increased selectivity toward CEs from different species. Replacement of the benzene rings with heterocyclic substituents increased the Ki values for the compounds toward three mammalian CEs when using o-nitrophenyl acetate as a substrate. Logarithmic plots of the Ki values versus the empirical resonance energy, the heat of union of formation energy, or the aromatic stabilization energy determined from molecular orbital calculations for the ring structures yielded linear relationships that allowed prediction of the efficacy of the diones toward CE inhibition. Using these data, we predicted that 2,2′-naphthil would be an excellent inhibitor of mammalian CEs. This was demonstrated to be correct with a Ki value of 1 nM being observed for a rabbit liver CE. In addition, molecular simulations of the movement of the ring structures around the dione dihedral indicated that the ability of the compounds to inhibit CEs was due, in part, to rotational constraints enforced by the dione moiety. Overall, these studies identify subdomains within the aromatic ethane-1,2-diones, that are responsible for CE inhibition.
A porous organic polymer supported Pd/Cu bimetallic catalyst for heterogeneous oxidation of alkynes to 1,2-diketones
Chen, Jianbin,Huang, Zhongye,Jia, Xiaofei,Song, Jiaxin,Xie, Congxia,Yang, Zhengyi,Zhang, Kai,Zhao, Jinyu,Zong, Lingbo
, p. 722 - 727 (2022/02/17)
A porous organic polymer (POP-POPh3) was readily prepared by oxidation of POP-PPh3 with H2O2. After coordination with PdCl2 and a co-catalyst of a CuBr2 precursor, a Pd/Cu bimetal-loaded porous organic polymer (Pd/Cu@POP-POPh3) was afforded. The NMR and XPS characterizations indicated that both Pd(ii) and Cu(ii) could coordinate with the PO bonds in the polymer. Furthermore, the catalyst has high surface areas, hierarchical porosity and good thermostability. The Pd/Cu@POP-POPh3 catalyst was successfully used in heterogeneous oxidation of alkynes with O2 as the oxidant to afford corresponding 1,2-diketones in high to excellent yields (76-99%). A series of alkynes with various functional groups performed well in the process. Remarkably, the heterogeneous catalyst can be reused for five cycles without significant loss of catalytic activity in oxidation of diphenylacetylene. This journal is
A Facile Synthesized Polymer Featuring B-N Covalent Bond and Small Singlet-Triplet Gap for High-Performance Organic Solar Cells
Pang, Shuting,Wang, Zhiqiang,Yuan, Xiyue,Pan, Langheng,Deng, Wanyuan,Tang, Haoran,Wu, Hongbin,Chen, Shanshan,Duan, Chunhui,Huang, Fei,Cao, Yong
supporting information, p. 8813 - 8817 (2021/03/16)
High-efficiency organic solar cells (OSCs) largely rely on polymer donors. Herein, we report a new building block BNT and a relevant polymer PBNT-BDD featuring B-N covalent bond for application in OSCs. The BNT unit is synthesized in only 3 steps, leading to the facile synthesis of PBNT-BDD. When blended with a nonfullerene acceptor Y6-BO, PBNT-BDD afforded a power conversion efficiency (PCE) of 16.1 % in an OSC, comparable to the benzo[1,2-b:4,5-b′]dithiophene (BDT)-based counterpart. The nonradiative recombination energy loss of 0.19 eV was afforded by PBNT-BDD. PBNT-BDD also exhibited weak crystallinity and appropriate miscibility with Y6-BO, benefitting of morphological stability. The singlet–triplet gap (ΔEST) of PBNT-BDD is as low as 0.15 eV, which is much lower than those of common organic semiconductors (≥0.6 eV). As a result, the triplet state of PBNT-BDD is higher than the charge transfer (CT) state, which would suppress the recombination via triplet state effectively.
Dithienobenzimidazole-containing conjugated donor–acceptor polymers: Synthesis and characterization
Harris, Jared D.,Stihl, Markus,Schmidt, Hans-Werner,Carter, Kenneth R.
, p. 60 - 69 (2019/01/03)
The synthesis of two new conjugated polymers based on the relatively under-exploited monomer, 5,8-dibromo-2-[5-(2-hexyldecyl)-2-thienyl]-1H-dithieno[3,2-e:2′,3′-g]benzimidazole (dithienobenzimidazole, DTBI), and either 4,7-bis[4-hexyl-5-(trimethylstannyl)-2-thienyl]-2,1,3-benzothiadiazole (BTD) or 2,6-bis(trimethylstannyl)-4,8-bis(5-(2-ethylhexyl) thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene (BDT) is described. The polymers were synthesized via Stille polycondensation and characterized by traditional methods (1H NMR, gel-permeation chromatography, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, thermal gravimetric analysis, differential scanning calorimetry, ultraviolet–visible spectroscopy, photoluminescence, and cyclic voltammetry). Prior to their synthesis, trimer structures were modeled by DFT calculations facilitating a further understanding of the systems' electronic and geometric structure. Polymers were titrated with acid and base to take advantage of their amphiprotic imidazole moiety and their optical response monitored with ultraviolet–visible spectroscopy. Finally, pristine polymer thin-films were treated with acid and base to evaluate (de)protonation's effect on system electronics, but thin-film degradation was encountered.
