5,5''-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':5',2''-terthiophene | 1259016-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5''-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':5',2''-terthiophene
• 英文别名: 4,4,5,5-Tetramethyl-2-[5-[5-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-[5-[5-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-1,3,2-dioxaborolane
• CAS: 1259016-23-3
• 化学式: C₂₄H₃₀B₂O₄S₃
• 分子量: 500.32
• InChiKey: BWDBXSNKLOZEKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2,6-diisopropylphenyl)-1-bromoperylene-3,4,9,10-tetracarboxydiimide 、 5,5''-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':5',2''-terthiophene 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到11-[5-[5-[5-[7,18-Bis[2,6-di(propan-2-yl)phenyl]-6,8,17,19-tetraoxo-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-11-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-7,18-bis[2,6-di(propan-2-yl)phenyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
  参考文献：
  名称：

  用于在分子聚集水平上调节光学特性的可控超分子结构

  摘要：

  在化学弱力和溶剂效应的关联驱动下，获得了噻吩取代的苝双酰亚胺的零到二维纳米结构，例如球体和块状结构。从三噻吩单元到固态苝双酰亚胺的光控分子内电荷转移可引起低色移和增强的荧光发射。

  DOI：

  10.1002/ejoc.201402460
• 作为产物：
  描述：

  2,2'-联噻吩-5-硼酸频哪醇酯 在 四(三苯基膦)钯 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 sodium carbonate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 正辛烷 、 乙醇 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 5,5''-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Synthesis of d-glucose and l-phenylalanine substituted phenylene–thiophene oligomers

  摘要：

  Phenylene-thiophene oligomers bearing peracetylated beta-D-glucose or N-BOC-L-phenylalanine as chiral substituents were synthesized in good yields by a versatile protocol based on the Suzuki-Miyaura cross-coupling reaction. Aryl iodides bearing the chiral biomolecules as substituents efficiently reacted with pinacol boronates of bi- or terthiophenes leading to the bio-functionalized oligomers in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.004

文献信息

• Iridium–bipyridine periodic mesoporous organosilica catalyzed direct C–H borylation using a pinacolborane
  作者：Yoshifumi Maegawa、Shinji Inagaki

  DOI：10.1039/c5dt00239g

  日期：——

  organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinacolato)diboron (B2pin2). The precatalyst could be handled without the use of a glove box. The catalyst was easily recovered from reaction mixtures by simple filtration

  据报道，铱（Ir）络合物固定在骨架（Ir-BPy-PMO）和吡萘甲硼烷（HBpin）内的含联吡啶配体的周期性介孔有机二氧化硅上，铱和铱的混合直接异构化催化芳烃和杂芳烃的非均相催化。Ir-BPy-PMO与便宜的bis（pinacolato）diboron（B 2 pin 2）相比，对便宜的HBpin苯的硼化反应显示出更高的催化活性。）。无需使用手套箱即可处理预催化剂。通过在空气中简单过滤，可以容易地从反应混合物中回收催化剂。回收的催化剂对于苯的硼酸酯化反应仍显示出至少三倍以上的良好催化活性。使用HBpin通过Ir-BPy-PMO成功地以高硼效率将各种芳烃和杂芳烃进行了硼化，而对于某些杂芳烃与B 2 pin 2进行的硼化却几乎没有观察到活性。。使用Ir-BPy-PMO和HBpin的系统还用于合成多硼化的基于噻吩的积木，其中包含梯形，并苯并噻吩和聚并噻吩骨架。稳定且可重复使用的固体催化剂与廉价的
• Improved stability of organic field-effect transistor performance in oligothiophenes including β-isomers
  作者：Minoru Ashizawa、Takuro Niimura、Yan Yu、Kazuma Tsuboi、Hidetoshi Matsumoto、Ryo Yamada、Susumu Kawauchi、Akihiko Tanioka、Takehiko Mori

  DOI：10.1016/j.tet.2012.02.004

  日期：2012.4

  Dialkyl quarter-and quinquethiophenes end-capped with beta-connected thiophenes are prepared, and the field-effect transistor (FET) properties are investigated. Molecular orbital calculation as well as the redox and optical measurements indicate that the beta-isomers have low-lying HOMO levels and large energy gaps compared with the alpha-isomers. Molecular packing of the dihexylquaterthiophene with beta-isomers consists of a typical herringbone motif analogous to the alpha-isomers. In the single crystal, the alkyl chains are extending in the tilted directions from the core molecular plane, but straightly extending in the thin films, resulting in even more perpendicular molecular arrangement to the substrate than the alpha-isomers. These beta-isomers show p-type FET performance comparable to the corresponding alpha-isomers, whereas all new oligothiophenes show air stability better than the corresponding alpha-isomers. In particular, dihexylquinquethiophene with beta-isomers has shown significantly improved air stability maintained over 270 days. This stabilization effect is ascribed to the low-lying HOMO level and the dense packing realized by perpendicular molecular arrangement. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of d-glucose and l-phenylalanine substituted phenylene–thiophene oligomers
  作者：Omar Hassan Omar、Francesco Babudri、Gianluca M. Farinola、Francesco Naso、Alessandra Operamolla、Adriana Pedone

  DOI：10.1016/j.tet.2010.11.004

  日期：2011.1

  Phenylene-thiophene oligomers bearing peracetylated beta-D-glucose or N-BOC-L-phenylalanine as chiral substituents were synthesized in good yields by a versatile protocol based on the Suzuki-Miyaura cross-coupling reaction. Aryl iodides bearing the chiral biomolecules as substituents efficiently reacted with pinacol boronates of bi- or terthiophenes leading to the bio-functionalized oligomers in good yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Controllable Supramolecular Architectures for Modulating Optical Properties on the Molecular Aggregation Level
  作者：Runsheng Jiang、Zheng Xue、Yongjun Li、Zhihong Qin、Yuliang Li、Daoben Zhu

  DOI：10.1002/ejoc.201402460

  日期：2014.8

  Driven by the association of chemical weak forces and solvent effects, zero- to two-dimensional nanostructures of thiophene-substituted perylene bisimide such as spheres and blocky structures were obtained. Light-controlled intramolecular charge transfer from the trithiophene unit to the perylene bisimide in the solid state can induce a hypochromatic shift and enhanced fluorescent emission.

  在化学弱力和溶剂效应的关联驱动下，获得了噻吩取代的苝双酰亚胺的零到二维纳米结构，例如球体和块状结构。从三噻吩单元到固态苝双酰亚胺的光控分子内电荷转移可引起低色移和增强的荧光发射。