1-(2'-thienyl)-2-(p-ethynylphenyl)ethyne | 264884-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2'-thienyl)-2-(p-ethynylphenyl)ethyne
• 英文别名: 1-(2'-thienyl)-2-(4-ethynylphenyl)ethyne；2-[2-(4-Ethynylphenyl)ethynyl]thiophene
• CAS: 264884-57-3
• 化学式: C₁₄H₈S
• 分子量: 208.284
• InChiKey: LJWZTSFASOVDIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  1-(2'-thienyl)-2-(p-ethynylphenyl)ethyne 在 正丁基锂 、 四氯化硅 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以65%的产率得到
  参考文献：
  名称：

  Synthesis and photoactivated insecticidal activity of tetraethynylsilanes

  摘要：

  A series of tetraethynylsilanes (TETS) have been synthesized by reaction of silicon tetrachloride (SiCl(4)) with Ar-C CLi, which was prepared in situ by treatment of Ar-C CH with n-BuLi For these TETS thus prepared. their photoactivated insecticidal activities against the 4th-instar larvae of Aedes albapictus (Skuse) were evaluated to enrich the structure-activity relationship. In particular, compound 8 exhibited excellent photoactivated insecticidal activity, the LC(50) value was 0.1346 mg; L(-1) under UV light treatment and the irradiation-generated enhancement in the activity was more than 69 58-fold, thus could be exploitable as ideal analog candidates in the search for new photoactivated insecticide leads. (C) 2009 Elsevier B.V All rights reserved

  DOI：

  10.1016/j.jphotobiol.2009.11.003
• 作为产物：
  描述：

  (4-iodobenzyl)triphenylphosphonium bromide 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 potassium tert-butylate 、 溴 、 碘 、 二乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 甲苯 为溶剂， 反应 100.5h， 生成 1-(2'-thienyl)-2-(p-ethynylphenyl)ethyne
  参考文献：
  名称：

  Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties

  摘要：

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.032

文献信息

• Synthesis and optical properties of conjugated N,N-dimethyl and thienyl end-capped 2,5-(arylethynyl)thiophene oligomer structures
  作者：J. Gonzalo Rodrı́guez、Antonio Lafuente、Laura Rubio、Jorge Esquivias

  DOI：10.1016/j.tetlet.2004.07.123

  日期：2004.9

  by the Cl2Pd(PPh3)2/CuI system, in good to excellent yields. The 2,5-di[(3′,5′-di(trimethylsilylethynyl)phenyl]x-1-ethynyl]thiophene oligomers were prepared by heterocoupling between 3′,5′-di[(trimethylsilylethynyl)phenyl]x-1-ethyne (n = 0–2) terminal acetylenes and 2,5-diiodothiophene, in excellent yields. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology

  通过在末端乙炔之间进行杂偶合，合成对位封端的（N，N-二甲基氨基苯基）和2'-噻吩基乙炔基2,5-噻吩低聚物结构：p-（N，N-二甲基氨基苯基）乙炔（3）[或1- （p-（N，N-二甲基氨基苯基）-2- p-（乙炔基苯基）乙炔，4]；p-（β-乙烯基-2'-噻吩基）苯基乙炔（E -9）[或p-（β-乙炔基- Cl 2 Pd（PPh 3）2催化的2'-噻吩基）苯基乙炔11]和2,5-二碘噻吩/ CuI系统，良率至良率。通过3，，5'-二[（三甲基甲硅烷基乙炔基）苯基] x -1-之间的杂合制备2,5-二[（3'，5'-二（三甲基甲硅烷基乙炔基）苯基] x -1-乙炔基]噻吩低聚物乙炔（n  = 0–2）末端乙炔和2,5-二碘噻吩，收率很好。通过特定的保护-脱保护方法有效地制备了末端乙炔。所有获得的乙炔基苯基化合物均显示出荧光辐射发射，红移为随着链共轭增加的波长。
• Structural, Photophysical, and Nonlinear Absorption Properties of <i>trans</i>-Di-arylalkynyl Platinum(II) Complexes with Phenyl and Thiophenyl Groups
  作者：Per Lind、Dan Boström、Marcus Carlsson、Anders Eriksson、Eirik Glimsdal、Mikael Lindgren、Bertil Eliasson

  DOI：10.1021/jp066569p

  日期：2007.3.1

  were shorter than that of a Pt(II) complex having two phenyl groups in the ligands. In order to elucidate the C-Pt bonding nature in the ground state, the 13C NMR chemical shift of the carbon directly bonded to Pt, the coupling constants 1JPtC, 2JPtC, and 1JPtP, and IR nuC[triple bond]C wavenumbers were obtained for 1, 2, and three other trans-diarylalkynyl Pt(II) complexes. X-ray diffraction data of 1

  具有配体中的苯硫基和苯基的两个Pt（II）配合物的反光功率限制和发光特性，反式-Pt（P（n-Bu）3）2（C [三键] C-Ar）2，其中Ar =研究了-C4H2S-C [三键] Cp-C6H4-n-C5H11（1）和-p-C6H4-C [三键] C-C4H3S（2）。发现荧光寿命在亚纳秒级，并且量子产率低，这与从激发单重态到三重态流形的快速系统间穿越相一致。1和2的磷光寿命短于在配体中具有两个苯基的Pt（II）配合物。为了阐明基态下的C-Pt键合性质，获得了直接键合到Pt上的碳的13C NMR化学位移，耦合常数1JPtC，2JPtC和1JPtP以及IR nuC [三键] C波数。一二 和其他三个反式二芳基炔基Pt（II）配合物。1和2的X射线衍射数据以及密度泛函理论计算的1、2和反式Pt（P（n-Bu）3）2（C [三键] Cp-C6H4-C [三键）模型的几何形状] C-C6H5）2
• Synthesis of conjugated 2-arylethynyl and 2-arylethenyl thiophene structures with optical properties
  作者：J.Gonzalo Rodrı́guez、Antonio Lafuente、Laura Rubio

  DOI：10.1016/j.tetlet.2004.05.104

  日期：2004.7

  Conjugated mono(arylethynyl)oligothiophene structures have been obtained starting with (E)-[1-(2'-thienyl)-2-(p-phenyl)]ethyne (E)-7 and 2-[p-(iodophenyl)ethynyl]thiophene 8. Conjugated nanostructures were synthesized by oxidative coupling between the terminal acetylenes (E)-7 and 8 to give, respectively, 1,4-di[(2-p-(iodophenyl)ethynyl)thienyl]-1,3-butadiyne and 1,4-di[(2-p-iodophenylethynyl)thienyl]-1,3-butadiyne. All the thiophene derivatives synthesized show an important fluorescence radiation emission, with a bathochromic shift, which increases with the conjugation of the chain. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties
  作者：J. Gonzalo Rodriguez、Jorge Esquivias、Antonio Lafuente、Laura Rubio

  DOI：10.1016/j.tet.2006.01.032

  日期：2006.3

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and photoactivated insecticidal activity of tetraethynylsilanes
  作者：Guang Shao、Ding-Xin Jiang、Han-Hong Xu、Wei Zeng、Hui-Juan Yu、Yong-Qing Tian

  DOI：10.1016/j.jphotobiol.2009.11.003

  日期：2010.1

  A series of tetraethynylsilanes (TETS) have been synthesized by reaction of silicon tetrachloride (SiCl(4)) with Ar-C CLi, which was prepared in situ by treatment of Ar-C CH with n-BuLi For these TETS thus prepared. their photoactivated insecticidal activities against the 4th-instar larvae of Aedes albapictus (Skuse) were evaluated to enrich the structure-activity relationship. In particular, compound 8 exhibited excellent photoactivated insecticidal activity, the LC(50) value was 0.1346 mg; L(-1) under UV light treatment and the irradiation-generated enhancement in the activity was more than 69 58-fold, thus could be exploitable as ideal analog candidates in the search for new photoactivated insecticide leads. (C) 2009 Elsevier B.V All rights reserved