3'-bromo-5-methyl-2,2':5',2''-terthiophene | 378790-17-1

• 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: 3'-bromo-5-methyl-2,2':5',2''-terthiophene
• 英文别名: 3'-bromo-5-methyl-2,2';5',2''-terthiophene；3-bromo-2-(5-methylthiophen-2-yl)-5-thiophen-2-ylthiophene
• CAS: 378790-17-1
• 化学式: C₁₃H₉BrS₃
• 分子量: 341.316
• InChiKey: LAYQTUOVBFZKQH-UHFFFAOYSA-N

物化性质

• 熔点：
  32.4-33.7 °C
• 沸点：
  380.9±37.0 °C(Predicted)
• 密度：
  1.545±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯硼酸 、 3'-bromo-5-methyl-2,2':5',2''-terthiophene 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以68%的产率得到3'-(4-methoxyphenyl)-5-methyl-2,2';5',2''-terthiophene
  参考文献：
  名称：

  立体与电子：多溴化噻吩的区域选择性交叉偶联

  摘要：

  已经开发了 2,3,5-三溴噻吩的区域选择性交叉偶联方法，其中选择性芳基-芳基偶联发生在 5 位，产率高达 63%。α 位和 β 位反应性的差异允许顺序区域选择性偶联首先在 2 位，然后是 3 位。这种区域选择性交叉偶联允许对三官能化噻吩的生成进行前所未有的控制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200701148
• 作为产物：
  描述：

  2-溴-5-甲基噻吩 在 溴 、 magnesium 作用下， 以 乙醚 、 氯仿 、 溶剂黄146 为溶剂， 反应 31.0h， 生成 3'-bromo-5-methyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Electropolymerization of Pd(II) Complexes Containing Phosphinoterthiophene Ligands

  摘要：

  A series of Pd complexes of 3'-diphenylphosphino-2,2:5'2"-terthiophene (1a, dppterth) in which the metal is coordinated in three different modes have been,prepared and electropolymerized, resulting in the formation of conductive thin films. In [Pd-2(mu -Cl-2)(dppterth-P,C-3)(2)] (3a), the metal is P,C-coordinated, in. [PdCl2(dppterth-P)(2)] (4a) the coordination is monodentate via the phosphine, and in [Pd(dppterth-P,C-3)(dppterth-P, S-1)] [PF6] (5a) both P,C- and P,S-coordination modes are found. In 5a, the coordinated thiophene is hemilabile and may be displaced by reaction with more strongly coordinating ligands such as isocyanides, To probe the effect of blocking the a-position of the terthienyl moiety with methyl groups, 3'-diphenylphosphino-5-methyl-2,2':5'2"-terthiophene (1b, Me-dppterth) and 3'-diphenylphosphino-5,5"-dimethyl-2,2':5'2"-terthiophene (1c, Me-2-dppterth) were prepared, and the corresponding series of Pd complexes was synthesized. One of these complexes, [Pd(Me-2-dppterth-P,C-3)(Me-2-dppterth-P,S-1)] [PF6] (5c), has been crystallographically characterized. The electropolymerized films prepared, from 5a react with isonitriles, and shifts in the absorption spectra of the electropolymerized materials are observed upon reaction. A Pd complex has also been prepared from 5-diphenylphosphino-2,2':5,'2"-terihiophene (2, 5dppterth), and this complex has been electropolymerized. All the electropolymerized thin films have been characterized using EDX analysis, which demonstrates good correspondence with the elemental analysis of the respective monomers, and the maximum conductivities of the films are near 10(-4) S cm(-1). Comparing the electropolymerization behavior of the complexes, along with their electrochemical and spectroscopic data, allows conclusions to be drawn regarding the involvement of pi -delocalization and the metal group in the conductivity of the Materials.

  DOI：

  10.1021/ja016465m

文献信息

• DIARYLETHENE COMPOUNDS AND USES THEREOF
  申请人：SWITCH MATERIALS, INC.

  公开号：US20160083398A1

  公开（公告）日：2016-03-24

  A compound according to Formula IA and IB, reversibly convertible under photochromic and electrochromic conditions between a ring-open isomer A and a ring-closed isomer B is provided. For substitutent groups, Z is N, O or S; each R 1 is independently selected from the group consisting of H, or halo; each R 2 is independently selected from the group consisting of H, halo, a polymer backbone, alkyl or aryl; or, when both R 2 together form —CH═CH— and form part of a polymer backbone; each R 3 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl; each R 4 is aryl; and each R 5 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl.

  本发明提供了一种按照式IA和IB的化合物，在光致变色和电致变色条件下，可在环开放异构体A和环闭合异构体B之间可逆地转化。对于取代基，Z为N、O或S；每个R1独立地选自H或卤素；每个R2独立地选自H、卤素、聚合物骨架、烷基或芳基；或者，当两个R2一起形成-CH═CH-并形成聚合物骨架的一部分时；每个R3独立地选自H、卤素、烷基、烷氧基、硫代烷基或芳基；每个R4为芳基；每个R5独立地选自H、卤素、烷基、烷氧基、硫代烷基或芳基。
• Diarylethene compounds and uses thereof
  申请人：SWITCH MATERIALS, INC.

  公开号：US10072023B2

  公开（公告）日：2018-09-11

  A compound according to Formula IA and IB, reversibly convertible under photochromic and electrochromic conditions between a ring-open isomer A and a ring-closed isomer B is provided. For substitutent groups, Z is N, O or S; each R1 is independently selected from the group consisting of H, or halo; each R2 is independently selected from the group consisting of H, halo, a polymer backbone, alkyl or aryl; or, when both R2 together form —CH═CH— and form part of a polymer backbone; each R3 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl; each R4 is aryl; and each R5 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl.

  提供了一种根据式 IA 和 IB 的化合物，该化合物在光致变色和电致变色条件下可在开环异构体 A 和闭环异构体 B 之间进行可逆转换。对于取代基，Z 是 N、O 或 S；每个 R1 独立地选自 H 或卤代；每个 R2 独立地选自 H、卤代、聚合物骨架、烷基或芳基；或者，当两个 R2 一起形成 -CH═CH- 并构成聚合物骨架的一部分时；每个 R3 独立地选自由 H、卤素、烷基、烷氧基、硫代烷基或芳基组成的组；每个 R4 是芳基；每个 R5 独立地选自由 H、卤素、烷基、烷氧基、硫代烷基或芳基组成的组。
• PHOTOCHROMIC AND ELECTROCHROMIC DIARYLCYCLOPENTENE DERIVATIVES AS OPTICAL FILTERS
  申请人：Switch Materials, Inc.

  公开号：EP2760969A1

  公开（公告）日：2014-08-06
• US20140256936A1
  申请人：——

  公开号：US20140256936A1

  公开（公告）日：2014-09-11
• US9227986B2
  申请人：——

  公开号：US9227986B2

  公开（公告）日：2016-01-05