2-bromo-3-(2-cyanoethylsulfanyl)thiophene | 499793-74-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-bromo-3-(2-cyanoethylsulfanyl)thiophene
• 英文别名: 3-[(2-Bromothiophen-3-yl)sulfanyl]propanenitrile；3-(2-bromothiophen-3-yl)sulfanylpropanenitrile
• CAS: 499793-74-7
• 化学式: C₇H₆BrNS₂
• 分子量: 248.167
• InChiKey: LRSKSSDJKUSDEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-3-(2-cyanoethylsulfanyl)thiophene 在 cesium hydroxide 、 四(三苯基膦)钯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 1,6-bis[2-(3,'4'-ethylenedioxythien-2'-yl)-3-thienylsulfanyl]hexane
  参考文献：
  名称：

  Electrochemical Synthesis of C₆₀-Derivatized Poly(thiophene)s from Tailored Precursors

  摘要：

  New series of C-60-derivatized bithiophenic precursors with low oxidation potential have been synthesized using the thiolate deprotection chemistry. The analysis of the electropolymerization of these compounds shows that the use of two-site precursors leads to polymers combining enhanced conjugation length, faster switching time, and improved stability under redox cycling. The unsuccessful attempts to identify the optical signature of the reduced forms of the attached C-60 by spectroelectrochemistry suggest that the PT backbone is unstable in the presence of the C-60 anion radical. Preliminary photoelectrochemical experiments on films deposited on platinum electrode reveal a significant enhancement of the photocurrent for the C-60-derivatized polymer when compared to a nonsubstituted reference polymer, indicating that these new materials are potentially useful for photovoltaic energy conversion.

  DOI：

  10.1021/ma034047r
• 作为产物：
  描述：

  3-[(2-cyanoethyl)sulfanyl]thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以90%的产率得到2-bromo-3-(2-cyanoethylsulfanyl)thiophene
  参考文献：
  名称：

  定向作用对四噻吩-C60二聚体光物理性质的影响。

  摘要：

  已经合成了两个四噻吩-[60]富勒烯二联体，其中C60单（4TsC）或双（4TdC）连接到末端噻吩环的内部β位。通过UV / Vis光谱和循环伏安法分析了这些供体-受体化合物的电子性质，并通过（时间分辨）光致发光（PL）和光致吸收（PIA）光谱分析了它们在溶液和固态下的光物理性质。柔性且受几何约束的4TsC和4TdC二元组在甲苯和邻二氯苯（ODCB）中均表现出从四噻吩到富勒烯的光诱导电荷转移。在甲苯中，通过间接机理在两个二元体中都发生了电荷转移，第一步是从4T（S1）态到C60（S1）态的单重态能量转移。在极性更大的ODCB中，来自4T（S1）的直接电子转移与能量转移竞争，并且观察到直接和间接电荷转移。供体和受体生色团在4TdC中的几何固定导致能量和电子转移的速率常数比柔性4TsC系统的常数大一个数量级。对于两种双电荷，电荷重组都非常快，这是从皮秒分辨的甲苯和ODCB中4T。+自由基阳离子

  DOI：

  10.1002/1521-3765(20021202)8:23<5415::aid-chem5415>3.0.co;2-z

文献信息

• Thiolate Chemistry: A Powerful and Versatile Synthetic Tool for Immobilization/Functionalization of Oligothiophenes on a Gold Surface
  作者：Truong Khoa Tran、Quentin Bricaud、Maïténa Oçafrain、Philippe Blanchard、Jean Roncali、Stéphane Lenfant、Sylvie Godey、Dominique Vuillaume、David Rondeau

  DOI：10.1002/chem.201003687

  日期：2011.5.9

  dithiol 4T 15 with two TMSE‐protected thiolate groups have been immobilized on a gold surface as monolayers that have been characterized by CV, ellipsometry, contact‐angle measurement, and X‐ray photoelectron spectroscopy (XPS). The results show that molecules 14 and 15 are doubly grafted with a horizontal orientation of the conjugated system relative to the surface. Furthermore, application of the d

  描述了一系列带有2-氰基乙基（CNE），2-三甲基甲硅烷基乙基（TMSE）和乙酰基（Ac）保护的硫醇盐基团的四噻吩（4T）的合成和表征。这些不同的保护基的顺序切割允许制备用二茂铁和/或烷硫醇链衍生的4T。这些化合物的电化学行为已通过循环伏安法（CV）在溶液中进行了分析。二茂铁衍生的二硫醇4T 14和具有两个TMSE保护的硫醇盐基团的二硫醇4T 15已被固定在金表面上，作为单层，已通过CV，椭偏，接触角测量和X射线光电子能谱（XPS）进行了表征）。结果表明，分子14和以共轭体系相对于表面的水平取向将图15所示的结构双重嫁接。此外，在15个单层上应用其余保护的硫醇盐基团的脱保护/烷基化顺序可实现有效的后功能化。
• Crown-Annelated Oligothiophenes as Model Compounds for Molecular Actuation
  作者：Bruno Jousselme、Philippe Blanchard、Eric Levillain、Jacques Delaunay、Magali Allain、Pascal Richomme、David Rondeau、Nuria Gallego-Planas、Jean Roncali

  DOI：10.1021/ja026819p

  日期：2003.2.1

  Crown-annelated quater- (4T) and sexithiophenes (6T) with oligooxyethylene chains of various lengths attached at the 3-positions of the terminal thiophene rings have been synthesized. Analysis of the cation-binding properties of the macrocycles by H-1 NMR and UV-vis spectroscopy reveals the formation of a 1:1 complex with Ba2+, Sr2+, or Pb2+ and shows that cation complexation results in a conformational transition in the pi-conjugated system. Theoretical analysis of this process by density functional methods predicts that this conformational transition results in a narrowing of the highest occupied-lowest unoccupied molecular orbital gap of the conjugated system with a decrease of the redox potentials (E-1(0) and E-2(0)) associated with the formation of the 4T cation radical and dication. Cyclic voltarmmetry shows that, depending on the binding constant, the presence of metal cation produces a negative or a positive shift of E-1(0) while E-2(0) always shifts negatively. This unusual behavior is discussed in terms of interplay between electrostatic interactions and conformational changes associated with cation binding.
• Electrogenerated poly(thiophenes) derivatized by bipyridine ligands and metal complexes
  作者：Bruno Jousselme、Philippe Blanchard、Maïtena Oçafrain、Magali Allain、Eric Levillain、Jean Roncali

  DOI：10.1039/b313291a

  日期：——

  The synthesis of a series of bithiophenic precursors of electrogenerated conjugated polymers functionalized by bipyridine ligands is described. The precursor structure involves two polymerizable groups attached at both ends of a bipyridine ligand and fixed at an internal beta-position of thiophene via an alkylsulfanyl or alkoxy spacer. Electrochemical and optical data show that the low polymerization potential resulting from the association of 3,4-ethylenedioxythiophene (EDOT) and alkylsulfanyl or alkoxy thiophene combined with the multi-site polymerization approach allows a straightforward electrosynthesis of extensively conjugated and stable functionalized polymers. On the basis of these results, iron and ruthenium complexes of these precursors have been synthesized and electropolymerized. The analysis of the electrochemical behavior of the resulting polymers shows that they exhibit the typical electrochemical signature of both the conjugated polythiophene backbone and the immobilized metal complex.
• Synthesis and Metal Cation Complexing Properties of Crown-Annelated Terthiophenes Containing 3,4-Ethylenedioxythiophene
  作者：Dora Demeter、Philippe Blanchard、Magali Allain、Ion Grosu、Jean Roncali

  DOI：10.1021/jo070699s

  日期：2007.7.1

  Macrocyclic systems derived from crown-annelated terthiophene involving a median EDOT unit have been synthesized by coupling diiodooligooxyethylene chains and bis(2-cyanoethylsulfanyl)terthiophene under high dilution conditions. The metal cation complexing properties of the compounds have been analyzed using H-1 NMR, UV-vis spectroscopy, and cyclic voltammetry. These various experiments provide consistent results showing that one of the compounds exhibits interesting complexing properties for Pb2+.