5,5''-diethynyl-2,2':5',2''-terthiophene | 200703-08-8

• 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: 5,5''-diethynyl-2,2':5',2''-terthiophene
• 英文别名: 5,5-diethynyl-2,2:5,2-terthiophene；2,5-Bis(5-ethynylthiophen-2-yl)thiophene
• CAS: 200703-08-8
• 化学式: C₁₆H₈S₃
• 分子量: 296.438
• InChiKey: MSDDMMFOULNUOV-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：

  氯化甲基汞 、 5,5''-diethynyl-2,2':5',2''-terthiophene 在 NaOH 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以74%的产率得到[MeHgCC([2,2':5',2'']terthiophene-5,5''-diyl)CCHgMe]
  参考文献：
  名称：

  寡噻吩和联噻唑的双（炔基）汞（II）配合物

  摘要：

  据报道，一类新型的双核汞（Ⅱ）双（炔基）配合物含有低聚噻吩和双噻唑作为主要的有机连接基。d 10汞（II）配合物[R'HgC⋮CRC⋮CHgR']（R =噻吩-2,5-二基，[2,2']联噻吩-5,5'-二基，[2,2'： 5'，2'']噻吩-5,5''-二基，4,4'-二（叔丁基）-2,2'-Bithiazole -5,5'-二基，4,4'-二（p-甲氧基亚苯基）-2,2'-噻唑-5,5'-二基; R'= Me，Ph）是在碱性介质下通过适当的氯化汞（II）前体与二乙炔基官能化的低聚噻吩和联噻唑的脱卤化氢反应高产率制备的。通过FTIR和NMR光谱以及FAB质谱对这些化合物进行结构解析。通过X射线晶体学确定的[MeHgC⋮CRC⋮CHgMe]（R =噻吩-2,5-二基，[2,2'] bithiophene-5,5'-二基）的固态分子结构显示出疏松在每种情况下，聚合物结构都是通过弱分子间非共价

  DOI：

  10.1021/om020517e
• 作为产物：
  描述：

  2,5-二(5-溴噻吩-2-基)噻吩 在 platinum(II) acetate copper(l) iodide 、 potassium carbonate 、 二异丙胺 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 40.5h， 生成 5,5''-diethynyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  新型乙炔基官能化的低聚噻吩及其双核铂配合物的合成与表征

  摘要：

  通过骨架中的低聚噻吩键合单元扩展π共轭的一系列硬杆炔烃，2,5-双（三甲基甲硅烷基乙炔基）噻吩Ia，2,5-二乙炔基噻吩Ib，5,5'-双（三甲基甲硅烷基乙炔基）-2,2 '-联噻吩IIa，5,5'-二乙炔基-2,2'-联噻吩IIb，5,5''-双（三甲基甲硅烷基乙炔基）-2,2'∶5'，2''-对噻吩IIIa和5,5''-二乙炔基制备了-2,2'∶5'，2″-三噻吩IIIb。用半当量的CH 2 Cl 2 -NHPr i 2中的二末端炔基低聚噻吩发色团Ib-IIIb处理复杂的反式-[PtPh（Cl）（PR 3）2 ]（R = Et或Bu n）。在室温下，CuI的存在提供了铂二聚体反式-[（Et 3 P）2 PhPt– C CR'C C–PtPh（PEt 3）2 ]（R'=噻吩二基1a，联噻吩二基2或叔噻吩二基3）和反式[[（Bu n 3 P）2 PhPt– C CR'C C–PtPh（PBu

  DOI：

  10.1039/a704708h

文献信息

• Syntheses, structures, two-photon absorption cross-sections and computed second hyperpolarisabilities of quadrupolar A–π–A systems containing E-dimesitylborylethenyl acceptors
  作者：Christopher D. Entwistle、Jonathan C. Collings、Andreas Steffen、Lars-Olof Pålsson、Andrew Beeby、David Albesa-Jové、Jacquelyn M. Burke、Andrei S. Batsanov、Judith A. K. Howard、Jackie A. Mosely、Suk-Yue Poon、Wai-Yeung Wong、Fatima Ibersiene、Sofiane Fathallah、Abdou Boucekkine、Jean-François Halet、Todd B. Marder

  DOI：10.1039/b905719f

  日期：——

  A series of bis(E-dimesitylborylethenyl)-substituted arenes, namely arene = 1,4-benzene, 1,4-tetrafluorobenzene, 2,5-thiophene, 1,4-naphthalene, 9,10-anthracene, 4,4′-biphenyl, 2,7-fluorene, 4,4′-E-stilbene, 4,4′-tolan, 5,5′-(2,2′-bithiophene), 1,4-bis(4-phenylethynyl)benzene, 1,4-bis(4-phenylethynyl)tetrafluorobenzene and 5,5″-(2,2′:5′,2″-terthiophene), have been synthesised viahydroboration of the corresponding diethynylarenes with dimesitylborane. Their absorption and emission maxima, fluorescence lifetimes and quantum yields are reported along with the two-photon absorption (TPA) spectra and TPA cross-sections for the 5,5′-bis(E-dimesitylborylethenyl)-2,2′-bithiophene and 5,5′-bis(E-dimesitylborylethenyl)-2,2′:5′,2″-terthiophene derivatives. The TPA cross-section of the latter compound of ca. 1800 GM is the largest yet reported for a 3-coordinate boron compound and is in the range of the largest values measured for quadrupolar compounds with similar conjugation lengths. The X-ray crystal structures of 1,4-benzene, 2,5-thiophene, 4,4′-biphenyl and 5,5″-(2,2′:5′,2″-terthiophene) derivatives indicate π-conjugation along the BCC–arene–CCB chain. Theoretical studies show that the second molecular hyperpolarisabilities, γ, in each series of compounds are generally related to the HOMO energy, which itself increases with increasing donor strength of the spacer. A strong enhancement of γ is predicted as the number of thiophene rings in the spacer increases.

  一系列双(E-二甲基丁烯基苯基)取代的烯烃，即烯 = 1,4-苯、1,4-四氟苯、2,5-噻吩、1,4-萘、9,10-蒽、4,4â²-联苯、2、7-芴、4,4â²-E-二苯乙烯、4,4â²-甲苯、5,5â²-（2,2â²-二噻吩）、1,4-双（4-苯乙炔基）苯、1,4-双（4-苯乙炔基）四氟苯和 5,5â³-（2,2â²：5,5â³-（2,2â²: 5â²,2â³-四噻吩）的合成是通过相应的二乙炔基烯烃与二美辛基硼烷的硼氢化反应实现的。报告了它们的吸收和发射最大值、荧光寿命和量子产率，以及 5,5â²-双（E-二甲酰基丁烯基苯基）-2,2â²-噻吩和 5,5â²-双（E-二甲酰基丁烯基苯基）-2,2â²:5â²,2â³-四噻吩衍生物的双光子吸收（TPA）光谱和 TPA 截面。后一种化合物的 TPA 横截面约为 1800 GM，是迄今为止所报道的三配位硼化合物中最大的，也在具有类似共轭长度的四极化合物所测得的最大值范围内。1,4-苯、2,5-噻吩、4,4â²-联苯和 5,5â³-（2,2â²:5â²,2â³-四噻吩）衍生物的 X 射线晶体结构表明，Ï-共轭沿着 BCCâareneâCCB 链进行。理论研究表明，各系列化合物中的第二分子超极性δ³ 通常与 HOMO 能量有关，而 HOMO 能量本身会随着间隔物供体强度的增加而增加。预计随着间隔物中噻吩环数量的增加，δ³ 也会强烈增强。
• End-Group Telechelic Oligo- and Polythiophenes by “Click” Reactions: Synthesis and Analysis via LC-ESI-TOF MS
  作者：Claudia Enders、Susanne Tanner、Wolfgang H. Binder

  DOI：10.1021/ma1016727

  日期：2010.10.26

  respective (H/H)-modified species. Additionally, MALDI methods were used for a qualitative assessment. Subsequent azide/alkyne “click” reaction with either 1-(6-azidohexyl)thymine or 5-((4-azidobenzoyl)amino)-N,N′-(6-(octanoylamino)pyridin-2-yl)isophthalamide using CuI, CuBr(PPh3)3, or CuI·P(OEt)3 as catalyst yielded the final products with attached hydrogen bonds as judged by LC-ESI-TOF methods. The described

  从远螯炔炔官能化的P3HT经由铜（I）催化的叠氮化物/炔“点击”反应开始，制备了具有复杂氢键基团的端基改性聚（3-己基噻吩）（P3HT）。预计最终的聚合物将排列成由交替的供体/受体聚合物组成的假嵌段共聚物，用于太阳能电池材料中。从溴-telechelic P3HT（M n = 2000 g / mol; M w / M n＝ 1.2）通过McCullough方法制备，随后进行额外的溴化反应，得到具有（80％Br / Br； 20％H / Br）端基的远螯P3HT，通过Sonogashira偶联制备了相应的α，ω-（三甲基甲硅烷基）乙炔基-P3HT。反应。首次使用LC-ESI-TOF方法对炔基-telechelic P3HT物种的端基进行了分析，证明形成了〜59％（乙炔基/乙炔基）和〜40％（乙炔基/ H）物种在α，ω-（三甲基甲硅烷基）乙炔基-P3HTs中，只有少量（〜1％）的相应（H /
• Design and synthesis of dinuclear alkynylplatinum(II) terpyridine complexes as sensitizers for light-harvesting
  作者：Eric Chi-Ho Kwok、Mei-Yee Chan、Keith Man-Chung Wong、Vivian Wing-Wah Yam

  DOI：10.1016/j.poly.2016.05.048

  日期：2016.12

  A class of dinuclear alkynylplatinum(II) terpyridine complexes has been successfully synthesized and characterized, and their photophysical, electrochemical and excited state properties have been revealed. These dinuclear alkynylplatinum(II) terpyridine complexes have been shown to serve as photosensitizers in light-harvesting processes. (C) 2016 Elsevier Ltd. All rights reserved.
• Alkynic compounds, their use as monomers in vacuum deposition polymerisation, thin films formed from these polymers and their use in electroluminescent devices
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：EP1170273B1

  公开（公告）日：2003-05-28
• Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties
  作者：Ali Shaygan Nia、Claudia Enders、Wolfgang H. Binder

  DOI：10.1016/j.tet.2011.10.096

  日期：2012.1

  The synthesis of layered donor/acceptor-materials based on perylenes (1a-c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (la-c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer. (C) 2011 Elsevier Ltd. All rights reserved.