1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮 | 1231160-84-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
• 英文名称: 1,3-dibromo-5-(3,7-dimethyloctyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• 英文别名: 1,3-dibromo-5-(3,7-dimethyloctyl)thieno[3,4-c]pyrrole-4,6-dione
• CAS: 1231160-84-1
• 化学式: C₁₆H₂₁Br₂NO₂S
• 分子量: 451.222
• InChiKey: CQAAQHZSZYVFKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Fmoc-D-缬氨酸 、 N^α-(tert-butoxycarbonyl)-N^ε-(allyloxycarbonyl)-L-lysine 、 N-芴甲氧羰基-L-谷氨酸 5-烯丙基酯 、 p-nitrophenoxycarbonyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 、 Fmoc-D-Dab(ivDde)-OH 、 1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮 在 哌啶 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成
  参考文献：
  名称：

  Structural Basis of Multivalent Binding to Wheat Germ Agglutinin

  摘要：

  The inhibition of carbohydrate protein interactions by tailored multivalent ligands is a powerful strategy for the treatment of many human diseases. Crucial for the success of this approach is an understanding of the molecular mechanisms as to how a binding enhancement of a multivalent ligand is achieved. We have synthesized a series of multivalent N-acetylglucosamine (GIcNAc) derivatives and studied their interaction with the plant lectin wheat germ agglutinin (WGA) by an enzyme-linked lectin assay (ELLA) and X-ray crystallography. The solution conformation of one ligand was determined by NMR spectroscopy. Employing a GIcNAc carbamate motif with alpha-configuration and by systematic variation of the spacer length, we were able to identify divalent ligands with unprecedented high WGA binding potency. The best divalent ligand has an IC(50) value of 9.8 mu M (ELLA) corresponding to a relative potency of 2350 (1170 on a valency-corrected basis, i.e., per mol sugar contained) compared to free GIcNAc. X-ray crystallography of the complex of WGA and the second best, closely related divalent ligand explains this activity. Four divalent molecules simultaneously bind to WGA with each ligand bridging adjacent binding sites. This shows for the first time that all eight sugar binding sites of the WGA dimer are simultaneously functional. We also report a tetravalent neoglycopeptide with an IC(50) value of 0.9 mu M being 25 500 times higher than that of GIcNAc (6400 times per contained sugar) and the X-ray structure analysis of its complex with glutaraldehyde-cross-linked WGA. Comparison of the crystal structure and the solution NMR structure of the neoglycopeptide as well as results from the ELLA suggest that the conformation of the glycopeptide in solution is already preorganized in a way supporting multivalent binding to the protein. Our findings show that bridging adjacent protein binding sites by multivalent ligands is a valid strategy to find high-affinity protein ligands and that even subtle changes of the linker structure can have a significant impact on the binding affinity.

  DOI：

  10.1021/ja101646k
• 作为产物：
  描述：

  5-(3,7-dimethyloctyl)thieno[3,4-c] pyrrole-4,6-dione 在 硫酸 、 1,3-二溴-1,3,5-三嗪-2,4,6-三酮 作用下， 生成 1,3-二溴-5-(2-己基癸基)-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
  参考文献：
  名称：

  Synthetic Control of Structural Order in N-Alkylthieno[3,4-c]pyrrole-4,6-dione-Based Polymers for Efficient Solar Cells

  摘要：

  The correlation between the nature of alkyl substituents on N-alkylthieno[3,4-c]pyrrole-4,6-dione (TPD)-based polymers and solar cell device performance has been investigated. After adjusting device parameters, these TPD-based polymers used with PC61BM provided photovoltaic responses ranging from 4.0% to 6.8%, depending on the size and shape of the alkyl solubilizing groups. Further, we have correlated the effect of the alkyl groups on the structural order and orientation of the polymer backbone using grazing incidence X-ray scattering analysis, and we have demonstrated how fine-tuning of these parameters can improve the power conversion efficiency.

  DOI：

  10.1021/ja103275u

文献信息

• ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS
  申请人：Brown Christopher T.

  公开号：US20110204341A1

  公开（公告）日：2011-08-25

  Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising: Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.

  可以用于有机电子器件和光伏电池的p型材料的高分子。化合物，单体，二聚体，三聚体和聚合物包括：可以实现良好的光伏效率和寿命。R基团可以提供可溶性，环境稳定性和光谱和/或电子性质的微调。可以制备不同的高分子微结构，以鼓励多重带隙和广泛而强烈的吸收。羰基可以与相邻的噻吩环相互作用，提供具有刚性的骨架，诱导平面性，并减少和/或消除分子内链扭曲缺陷。包含苯并噻吩和/或苯并噻二唑结构的高分子可以显示出特别高的性能。
• ORGANIC SEMICONDUCTOR MATERIAL
  申请人：Toyobo Co., Ltd.

  公开号：EP3106484A1

  公开（公告）日：2016-12-21

  Provided are: a macromolecular compound for providing an organic semiconductor material exhibiting excellent conversion efficiency; a starting-material compound having high material design freedom; and methods for producing the same. The macromolecular compound according to the present invention comprising a benzobisthiazole structural unit represented by the formula (1): [in the formula (1), T1 and T2 each independently represent an alkoxy group, a thioalkoxy group, a thiophene ring optionally substituted by a hydrocarbon group or an organosilyl group, a thiazole ring optionally substituted by a hydrocarbon group or an organosilyl group, or a phenyl group optionally substituted by a hydrocarbon group, an alkoxy group, a thioalkoxy group, an organosilyl group, a halogen atom or a trifluoromethyl group; and B1 and B2 each represent a thiophene ring optionally substituted by a hydrocarbon group, a thiazole ring optionally substituted by a hydrocarbon group, or an ethynylene group].

  本发明提供了：一种用于提供具有优异转换效率的有机半导体材料的大分子化合物；一种具有高材料设计自由度的起始材料化合物；以及生产该化合物的方法。 根据本发明的大分子化合物包括由式（1）表示的苯并二噻唑结构单元： 式（1）中，T1 和 T2 各自独立地代表烷氧基、硫代烷氧基、任选被烃基或有机硅基取代的噻吩环、任选被烃基或有机硅基取代的噻唑环、或任选被烃基、烷氧基、硫代烷氧基、有机硅基、卤素原子或三氟甲基取代的苯基；B1 和 B2 分别代表任选被烃基取代的噻吩环、任选被烃基取代的噻唑环或乙炔基]。
• Organic semiconductor material
  申请人：TOYOBO CO., LTD.

  公开号：US10211401B2

  公开（公告）日：2019-02-19

  Provided are: a macromolecular compound for providing an organic semiconductor material exhibiting excellent conversion efficiency; a starting-material compound having high material design freedom; and methods for producing the same. The macromolecular compound according to the present invention comprising a benzobisthiazole structural unit represented by the formula (1): [in the formula (1), T1 and T2 each independently represent an alkoxy group, a thioalkoxy group, a thiophene ring optionally substituted by a hydrocarbon group or an organosilyl group, a thiazole ring optionally substituted by a hydrocarbon group or an organosilyl group, or a phenyl group optionally substituted by a hydrocarbon group, an alkoxy group, a thioalkoxy group, an organosilyl group, a halogen atom or a trifluoromethyl group; and B1 and B2 each represent a thiophene ring optionally substituted by a hydrocarbon group, a thiazole ring optionally substituted by a hydrocarbon group, or an ethynylene group].

  本发明提供了：一种用于提供具有优异转换效率的有机半导体材料的大分子化合物；一种具有高材料设计自由度的起始材料化合物；以及生产该化合物的方法。 根据本发明的大分子化合物包括由式（1）表示的苯并二噻唑结构单元： [在式 (1) 中，T1 和 T2 各自独立地代表烷氧基、硫代烷氧基、任选被烃基或有机硅基取代的噻吩环、任选被烃基或有机硅基取代的噻唑环，或任选被烃基、烷氧基、硫代烷氧基、有机硅基、卤素原子或三氟甲基取代的苯基；B1 和 B2 分别代表任选被烃基取代的噻吩环、任选被烃基取代的噻唑环或乙炔基]。
• US8968885B2
  申请人：——

  公开号：US8968885B2

  公开（公告）日：2015-03-03
• [EN] ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS<br/>[FR] POLYMÈRES ET DISPOSITIFS ORGANIQUES ÉLECTRIQUES, COMPRENANT DES CELLULES PHOTOVOLTAÏQUES ET DES POLYMÈRES À BASE DE DICÉTONE
  申请人：PLEXTRONICS INC

  公开号：WO2011028827A2

  公开（公告）日：2011-03-10

  Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising formula (I); Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.