2,2'-bis(2-thienyl)propane | 2455-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,2'-bis(2-thienyl)propane
• 英文别名: 2,2-bis(2-thienyl)propane；2,2'-(1-methyl-ethane-1,1-diyl)-bis-thiophene；2,2-di-[2]thienyl-propane；2,2-Di-[2]thienyl-propan；2,2'-(Propane-2,2-diyl)dithiophene；2-(2-thiophen-2-ylpropan-2-yl)thiophene
• CAS: 2455-64-3
• 化学式: C₁₁H₁₂S₂
• 分子量: 208.348
• InChiKey: GLBZUEUNJBRBHY-UHFFFAOYSA-N

物化性质

• 沸点：
  74-76 °C(Press: 0.05 Torr)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-bis(2-thienyl)propane 在 乙醚 、 alkaline sodium hypobromite solution 、 碘 、 乙酸酐 、 镍 、 sodium carbonate 作用下， 生成 6,6-二甲基十一烷二酸
  参考文献：
  名称：

  Badger et al., Journal of the Chemical Society, 1954, p. 4162,4165

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-噻吩甲基)噻吩 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以53%的产率得到2,2'-bis(2-thienyl)propane
  参考文献：
  名称：

  An Electrochemically Prepared Small-Bandgap Poly(biheteroarylidenemethine):  Poly{bi[(3,4-ethylenedioxy)thienylene]methine}

  摘要：

  The electrochemical polymerization of bis(2-thienyl)methanes carrying substituents either on the methylene carbon or on the thiophene rings is reported. Poly(dithienylenemethylene)s are formed which undergo in-situ dehydrogenation to poly(dithienylenemethine)s. Bis(3,4-ethylenedioxythienyl)-methane gave a very low-gap material (0.4 V onset-based bandgap). This value is much lower than those previously reported for chemically prepared materials having the same conjugated backbone but carrying different substituents. The unsubstituted bis(2-thienyl)methane gives a similar low-gap polymer as well, but overoxidation and probably misjunction defects are present. No polymer was formed in the case of 2,2'-bis(2-thienyl)propane, for which the possibility of producing a conjugated polymer is precluded by the lack of at least one hydrogen atom on the carbon bridging the thiophene units. Full electrochemical and optical characterization data for the polymers are reported, and the polymerization and p- and n-doping processes are discussed.

  DOI：

  10.1021/ma025919c

文献信息

• Synthesis of novel conjugated oligomers for second-order nonlinear optics: incorporation of a central spacer as a conjugation modulator
  作者：Jian Xin Zhang、Philippe Dubois、Robert Jérôme

  DOI：10.1039/a606547c

  日期：——

  A new series of second-order nonlinear optical chromophores has been synthesized that consists of a conjugated segment end-capped with an electron acceptor and an electron donor, respectively, and a central spacer intended to modulate the electro-optical effect. Conjugated chains have been tailored with trans-vinylene-1,5-thienylene as the building unit and N,N-dimethylamino and nitro groups as the donor–acceptor pair. Four spacers have been incorporated into the central part of the conjugated oligomers, which range from saturated to totally unsaturated functions, i.e. from methylene to vinylene units. The general strategy relies upon two consecutive Wittig or Wittig–Horner reactions between the spacer precursor and an aromatic phosphonium or phosphonate bearing the strong electron donor and the acceptor, respectively. Two synthetic pathways have been studied. The first procedure is based on the use of a symmetric precursor for the spacer. However, a reaction byproduct is formed, which must be removed and decreases the reaction efficiency. The second approach requires an asymmetric precursor for the spacer, the synthesis of which is a multistep process. In order to evaluate the effect of the spacer, a completely conjugated oligomer has been prepared by the one-step coupling of two conjugated segments end-functionalized by the electron donor and the acceptor, respectively.

  一种新的二阶非线性光学染料系列已被合成，该系列由一个共轭段组成，两端分别封端为电子受体和电子给体，并包含一个中心间隔器，旨在调节电光效应。共轭链使用反式乙烯-1,5-噻吩单元作为构建单元，N,N-二甲基氨基和硝基作为给体–受体对。四种间隔器被引入到共轭 oligomer 的中央部分，这些间隔器从饱和功能到完全不饱和功能，即从亚甲基到乙烯基单元。一般策略依赖于间隔器前体与带有强电子给体和受体的芳香族膦盐或膦酸酯之间的两次连续 Wittig 或 Wittig–Horner 反应。研究了两条合成路径。第一种程序基于使用对称前体作为间隔器。然而，会形成一个反应副产物，必须去除，这降低了反应效率。第二种方法需要不对称的间隔器前体，其合成是一个多步过程。为了评估间隔器的影响，通过将两个分别被电子给体和受体功能化的共轭段进行一步耦合，制备了一个完全共轭的 oligomer。
• The Use of<i>N</i>,<i>N</i>-Dimethylformamide–Sulfonyl Chloride Complex for the Preparation of Thiophenesulfonyl Chlorides
  作者：Tyo Sone、Yukio Abe、Norio Sato、Manabu Ebina

  DOI：10.1246/bcsj.58.1063

  日期：1985.3

  A 1:1 N,N-dimethylformamide–SO2Cl2 complex was found to be a useful agent for the one-step preparation of thiophenesulfonyl chlorides.

  发现1:1的N,N-二甲基甲酰胺–SO2Cl2复合物是一种有效的试剂，可用于一步法合成噻吩磺酰氯。
• Synthesis of Sexithiophene-Bridged Cage Compound: A New Class of Three-Dimensionally Expanded Oligothiophenes
  作者：Kazuhiko Adachi、Yasukazu Hirao、Kouzou Matsumoto、Takashi Kubo、Hiroyuki Kurata

  DOI：10.1021/ol5027816

  日期：2014.11.21

  A bicyclo-type cage-shaped compound consisting of three sexithiophenes was successfully synthesized and characterized by NMR, HRMS, and X-ray crystallographic analysis. The strained cage architecture was reflected in the blue-shifted absorption spectrum relative to its linear analogue. Intramolecular interaction between three-dimensionally fixed sexithiophenes was suggested by electrochemical analysis

  已成功合成了由三个六噻吩组成的双环型笼状化合物，并通过NMR，HRMS和X射线晶体学分析对其进行了表征。相对于其线性类似物，应变笼结构反映在蓝移吸收光谱中。通过电化学分析表明三维固定的六噻吩之间的分子内相互作用。
• Heterocyclic organic compounds as electron donors for polyolefin catalysts
  申请人：Formosa Plastics Corporation USA

  公开号：US10442874B2

  公开（公告）日：2019-10-15

  Heterocyclic organic compounds are used as electron donors in conjunction with solid Ziegler-Natta type catalyst in processes in which polyolefins such as polypropylene are produced. The electron donors may be used in the preparation of solid catalyst system, thus serving as “internal electron donors,” or they may be employed during or prior to polymerization with the co-catalyst as “external electron donors.”

  在生产聚丙烯等聚烯烃的工艺中，杂环有机化合物与固体齐格勒-纳塔催化剂一起用作电子供体。电子供体可以在制备固体催化剂体系时使用，从而作为 "内部电子供体"，也可以在与助催化剂聚合时或聚合前作为 "外部电子供体 "使用。
• Condensation of Thiophene and Homologs with Ketones
  作者：John W. Schick、Duncan J. Crowley

  DOI：10.1021/ja01147a532

  日期：1951.3