2,5-bis[3-(1-ethynyl)-thien-2-yl]thiophene | 1246464-28-7

• 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: 2,5-bis[3-(1-ethynyl)-thien-2-yl]thiophene
• 英文别名: 3,3''-diethynyl-2,2':5',2''-terthiophene；A2T3；2,5-Bis(3-ethynylthiophen-2-yl)thiophene；2,5-bis(3-ethynylthiophen-2-yl)thiophene
• CAS: 1246464-28-7
• 化学式: C₁₆H₈S₃
• 分子量: 296.438
• InChiKey: WBYISBAARRPABC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,5-bis[3-(1-ethynyl)-thien-2-yl]thiophene 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以3%的产率得到thieno[3,2-g:4,5-g']bis[1]benzothiophene
  参考文献：
  名称：

  Synthesis and Properties of Ethene-Bridged Terthiophenes

  摘要：

  A method for the facile synthesis of ethene-bridged terthiophenes (EBTTs) in two steps has been developed. The first step is a double Sonogashira coupling between 3',4'-dibromo-2,2':5',2 ''-terthiophene and terminal alkynes to give dialkynylated terthiophenes, and the second step is a cyclization reaction to afford EBTTs. The fundamental physical properties of EBTTs were also studied.

  DOI：

  10.1021/acs.orglett.5b02417
• 作为产物：
  描述：

  3,3″,5,5″-tetrabromo-2,2′:5′,2″-terthiophene 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2,5-bis[3-(1-ethynyl)-thien-2-yl]thiophene
  参考文献：
  名称：

  A Terthiophene-Containing Alkynylplatinum Terpyridine Pacman Complex: Controllable Folding/Unfolding Modulated by Weak Intermolecular Interactions

  摘要：

  Folded and unfolded solid-state structures of a bimetallic alkynylplatinum terpyridine complex with a flexible terthiophene linker have been obtained. Weak intermolecular interactions including pi-pi stacking and C-H center dot center dot center dot O and C-H center dot center dot Cl interactions as well as Cl-pi interactions stabilize the folded structure. In solution, folding is studied by electronic absorption spectroscopy and H-1 and NOESY NMR experiments.

  DOI：

  10.1021/ic400338v

文献信息

• Photophysical Properties and Electropolymerization of Gold Complexes of 3,3′′-Diethynyl-2,2′:5′,2′′-terthiophene
  作者：Angela M. Kuchison、Michael O. Wolf、Brian O. Patrick

  DOI：10.1021/ic100961w

  日期：2010.10.4

  The preparation and crystal structures of 3,3′′-diethynyl-2,2′:5′,2′′-terthiophene (A2T3) and three Au(I) complexes containing this ligand are reported. One of the complexes, Au2(dppm)(A2T3), has a short Au−Au distance (3.1969 Å) because of an aurophilic interaction. UV/vis absorption and emission spectra of the complexes and ligand at 298 and 85 K and photoinduced electron transfer to methyl viologen

  报道了3,3'-二乙炔基-2,2'：5'，2''-噻吩（A 2 T 3）和含有该配体的三种Au（I）配合物的制备和晶体结构。络合物之一Au 2（dppm）（A 2 T 3）由于亲酸作用而具有较短的Au-Au距离（3.1969Å）。报道了配合物和配体在298和85 K下的UV / vis吸收和发射光谱，以及光诱导的电子转移至甲基紫精。可以使2 T 3和两个络合物电聚合，并通过X射线光电子能谱（XPS）和循环伏安法对所得的含金薄膜进行表征。
• Synthesis and Properties of Ethene-Bridged Terthiophenes
  作者：Koichi Mitsudo、Hidehiko Sato、Arata Yamasaki、Natsuyo Kamimoto、Jun Goto、Hiroki Mandai、Seiji Suga

  DOI：10.1021/acs.orglett.5b02417

  日期：2015.10.2

  A method for the facile synthesis of ethene-bridged terthiophenes (EBTTs) in two steps has been developed. The first step is a double Sonogashira coupling between 3',4'-dibromo-2,2':5',2 ''-terthiophene and terminal alkynes to give dialkynylated terthiophenes, and the second step is a cyclization reaction to afford EBTTs. The fundamental physical properties of EBTTs were also studied.
• A Terthiophene-Containing Alkynylplatinum Terpyridine Pacman Complex: Controllable Folding/Unfolding Modulated by Weak Intermolecular Interactions
  作者：Yang Cao、Michael O. Wolf、Brian O. Patrick

  DOI：10.1021/ic400338v

  日期：2013.5.20

  Folded and unfolded solid-state structures of a bimetallic alkynylplatinum terpyridine complex with a flexible terthiophene linker have been obtained. Weak intermolecular interactions including pi-pi stacking and C-H center dot center dot center dot O and C-H center dot center dot Cl interactions as well as Cl-pi interactions stabilize the folded structure. In solution, folding is studied by electronic absorption spectroscopy and H-1 and NOESY NMR experiments.