3-bromo-2-(2-bromophenyl)benzo[b]thiophene | 1263143-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-bromo-2-(2-bromophenyl)benzo[b]thiophene
• 英文别名: 3-Bromo-2-(2-bromophenyl)-1-benzothiophene；3-bromo-2-(2-bromophenyl)-1-benzothiophene
• CAS: 1263143-03-8
• 化学式: C₁₄H₈Br₂S
• 分子量: 368.092
• InChiKey: LSEBXVUHHNUUBU-UHFFFAOYSA-N

物化性质

• 熔点：
  72.5-73.3 °C
• 沸点：
  429.7±30.0 °C(Predicted)
• 密度：
  1.747±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-2-(2-bromophenyl)benzo[b]thiophene 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 10-methyl-10-phenyl-10H-benzo[b]phosphindolo[2,3-d]thiophen-10-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Dually Switchable Heterotetracenes: Addressing the Photophysical Properties and Self-Organization of the P−S System

  摘要：

  New ladder-type, phosphorus- and sulfur-based heterotetracenes were synthesized, which allowed the engineering of the materials' properties by exploitation of the different reactivities between sulfur and phosphorus. P-31 NMR. spectroscopy and X-ray crystallographic studies revealed that the different electronic effects of the secondary heteroatom, sulfur, influence not only the conjugation in the heterotetracene core but also the behavior of the phosphorus center. UV-vis and fluorescence spectroscopy showed that the scaffold's band gap is mainly controlled by the electronic nature of sulfur, while the fluorescence quantum yield highly depends on the electronic nature of phosphorus. Cyclic voltammetry indicated that the redox properties of the system could be altered by selective modification of the respective heteroatom (oxidation of sulfur and/or functionalization of trivalent phosphorus). Importantly, oxidation of the phosphorus center results in enhanced reduction features of the heterotetracene system, and oxidation of the sulfur center further enhances the electron acceptor character of the core. Theoretical calculations provided insights on both selectivity of phosphorus chemistry and communication between the two heteroatoms (sulfur and phosphorus). Macroscopic self-organization of the heterotetracenes was observed when the tetracene core is functionalized with pendant functional groups. Preliminary results showed that extension of the molecule with an alkyl chain along the long axis of molecules induces the formation of ID microfibers, which was confirmed by fluorescence microscopy and scanning electron microscopy.

  DOI：

  10.1021/ja108081b
• 作为产物：
  描述：

  2-溴苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴 、 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成 3-bromo-2-(2-bromophenyl)benzo[b]thiophene
  参考文献：
  名称：

  含15和16族元素的苯并噻吩稠合的苯并杂杂环的一般合成，结构和光学性质

  摘要：

  通过通用方法合成了一系列含有第15组（N，P，As和Sb）和第16组（O，S，Se和Te）元素的苯并噻吩并[3,2- b ]苯并杂环。X射线分析表明，所有的四环杂并苯骨架都是平面的。与第15族-杂蒽相比，在第16族-杂蒽的激发能和它们的原子半径之间发现线性关系。进行密度泛函理论计算和电化学测量以了解结构与光学性质之间的关系。

  DOI：

  10.1016/j.tet.2016.10.048

文献信息

• Chiral Control in Pentacoordinate Systems: The Case of Organosilicates
  作者：Leon J. P. van der Boon、Laurens van Gelderen、Tim R. de Groot、Martin Lutz、J. Chris Slootweg、Andreas W. Ehlers、Koop Lammertsma

  DOI：10.1021/acs.inorgchem.8b01861

  日期：2018.10.15

  Chirality at the central element of pentacoordinate systems can be controlled with two identical bidentate ligands. In such cases the topological Levi-Desargues graph for all the Berry pseudorotations (BPR, max. 20) reduces to interconnected inner and outer "circles" that represent the dynamic enantiomer pair. High enough barriers of the BPR crossovers between the two circles is all what is needed

  五配位系统中心元素的手性可以用两个相同的二齿配体控制。在这种情况下，所有 Berry 假旋转（BPR，最大 20）的拓扑 Levi-Desargues 图都会简化为代表动态对映体对的相互连接的内部和外部“圆”。两个环之间的 BPR 交叉势垒足够高就可以确定手性完整性。这通过计算和实验说明了除 Me (a)、Et (b)、Ph (c) 或 F (d) 基团外还带有两个双齿 2-(苯基)苯并[b]-噻吩的有机硅酸盐 7 和 10或2-(苯基)萘基配体，分别。四有机硅烷前体9的对映体可以通过柱色谱法分离。它们的手性完整性在形成硅酸盐时持续存在。CD 光谱报告为 10c。氟衍生物10d的负电性F取代基位于赤道位置，对水解稳定，其对映体在环境温度下不会外消旋，而10c的对映体则缓慢外消旋。
• Circularly Polarized Luminescence from Chiral Spiro Molecules: Synthesis and Optical Properties of 10,10′-Spirobi(indeno[1,2-<i>b</i>][1]benzothiophene) Derivatives
  作者：Ko Takase、Keiichi Noguchi、Koji Nakano

  DOI：10.1021/acs.orglett.7b02337

  日期：2017.10.6

  S-dioxide units were synthesized as a new family of circularly polarized luminescence (CPL) materials. Oxidation of the thiophene unit to its S,S-dioxide provided significant changes in photophysical properties such as much higher fluorescence quantum yield and positive solvatochromism in photoluminescence spectra. Density functional theory calculations qualitatively demonstrated the observed absorption properties

  合成了具有噻吩和/或噻吩S，S-二氧化物单元的手性螺环多环芳族化合物，作为新的圆偏振发光（CPL）材料系列。噻吩单元被氧化成S，S-二氧化物会显着改变光物理性质，例如更高的荧光量子产率和光致发光光谱中的正溶剂化色度。密度泛函理论计算定性地证明了观察到的吸收特性。制备的手性螺环化合物对小有机分子表现出强烈的CPL信号，并且具有相对较大的不对称因子。
• Germanium-Bridged 2-Phenylbenzoheteroles as Luminophores Exhibiting Highly Efficient Solid-State Fluorescence
  作者：Masaki Shimizu、Daiki Ryuse、Takumi Kinoshita

  DOI：10.1002/chem.201703235

  日期：2017.10.17

  for organic luminophores that exhibit highly efficient solid-state fluorescence. It is found that [1]benzogermolo[3,2-b]indole, -benzofuran, and -thiophene-S,S-dioxide emit violet-to-blue light with good-to-high quantum yields in powder form, demonstrating the high potential of such bilaterally unsymmetrical germylene-bridged biaryls as solid-state light-emitting materials (see scheme).

  锗桥：在2-苯基苯并杂环上添加Ge桥作为有机发光体的新分子设计原理是有效的，有机发光体表现出高效的固态荧光。发现[1] benzogermolo [3,2- b ]吲哚，-苯并呋喃和-噻吩-S，S-二氧化物以粉状形式发射紫红色到蓝色的光，具有良好到高的量子产率，证明了这种双侧不对称的亚甲基桥接的联芳基作为固态发光材料的潜力很大（请参见方案）。
• Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades
  作者：Raquel Barroso、María‐Paz Cabal、Rosana Badía‐Laiño、Carlos Valdés

  DOI：10.1002/chem.201503080

  日期：2015.11.9

  The Pd‐catalyzed reaction between 2,2′‐dibromobiphenyls and related systems with tosylhydrazones gives rise to new π‐extended conjugated polycarbo‐ and heterocycles through an autotandem process involving a cross‐coupling reaction followed by an intramolecular Heck cyclization. The reaction shows wide scope regarding both coupling partners. Cyclic and acyclic tosylhydrazones can participate in the

  2,2'-二溴代二苯与相关系统与甲苯磺酰azo之间的Pd催化反应通过涉及交叉偶联反应然后进行分子内Heck环化的自动串联过程，产生了新的π-扩展的共轭聚碳环和杂环。对于两个偶合伙伴，反应显示出广泛的范围。环状和无环的甲苯磺酰can可以参与该过程。另外，已经使用了多种芳族和杂芳族二溴代衍生物，从而导致了一系列具有芴或a啶中心核并包含联萘基，噻吩，苯并噻吩和吲哚基团的多种支架。适当的四溴化系统的应用通过两个连续的串联级联反应导致了更大的结构复杂性。通过吸收和发射光谱研究了所选化合物的光物理性质。鉴定出具有非常高的量子产率的荧光分子，显示出该方法在开发具有令人感兴趣的光电特性的分子中的潜力。
• Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties
  作者：Koji Nakano、Ko Takase、Keiichi Noguchi

  DOI：10.3390/molecules27165103

  日期：——

  aromatic metamorphosis. The absorption and emission properties of the obtained furan-containing chiral spiro-fused PACs are apparently different from those of their thiophene analogs that have been reported, owing to the increased electron-richness of furan compared to thiophene. All of the furan-containing chiral spiro-fused PACs were found to be circularly polarized luminescent materials.

  螺稠合多环芳族化合物 (PAC) 作为刚性手性支架受到越来越多的关注。然而，含呋喃的螺稠合 PAC 非常有限。在这里，我们设计了螺[茚并[1,2- b ][1]苯并呋喃-10,10'-茚并[1,2- b ][1]苯并噻吩]作为含有呋喃的螺稠合PAC的新家族单元。该化合物以对映体形式成功合成，并转化为其S , S-二氧化物衍生物和含吡咯的类似物通过芳族变态。由于与噻吩相比，呋喃的电子富集度增加，所获得的含呋喃手性螺稠合 PAC 的吸收和发射特性明显不同于已报道的噻吩类似物。发现所有含呋喃的手性螺稠合 PAC 都是圆偏振发光材料。