5-{[[2,2'-联噻吩]-5-基}噻吩-2-腈 | 110230-97-2

• 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
• 中文名称: 5-{[[2,2'-联噻吩]-5-基}噻吩-2-腈
• 英文名称: 2-cyano-alpha-terthiophene
• 英文别名: 2,2':5',2"-terthiophene-5-carbonitrile；2,2':5',2''-terthiophene-5-carbonitrile；5-cyano-2,2':5',2''-terthiophene；(2,2':5',2''-Terthiophenyl)-5-carbonitrile；5-(5-thiophen-2-ylthiophen-2-yl)thiophene-2-carbonitrile
• CAS: 110230-97-2
• 化学式: C₁₃H₇NS₃
• 分子量: 273.403
• InChiKey: YXNZJCUXYIKKRE-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  420.1±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-{[[2,2'-联噻吩]-5-基}噻吩-2-腈 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以72%的产率得到2,2':5',2''-terthiophene-5-carboxamide
  参考文献：
  名称：

  Soucy-Breau, Chantal; MacEachern, Anita; Leitch, Leonard C., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 2, p. 411 - 416

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-双(2-噻吩基)-1,4-丁二酮 在 磺酰氯 、 双(三环己基锡(IV))硫醚 、 三氯化硼 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 5-{[[2,2'-联噻吩]-5-基}噻吩-2-腈
  参考文献：
  名称：

  Novel protein kinase C inhibitors: α-terthiophene derivatives

  摘要：

  A series of alpha-terthiophene derivatives were prepared and their protein kinase C inhibitory activity were evaluated. The aldehyde derivatives were most potent inhibitors (IC50 < 1 mu M). alpha-Terthiophene monoaldehyde was inactive in the inhibitions of protein kinase A, mitogen activated protein kinase and protein tyrosine kinase. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00468-5

文献信息

• Synthesis and Photovoltaic Properties of Donor–Acceptor Oligothiophene Derivatives Possessing Mesogenic Properties
  作者：Li Guan、Juan Wang、Jiale Huang、Chuanyu Jiang、Ming La、Ping Liu、Wenji Deng

  DOI：10.1080/00397911.2010.519845

  日期：2011.12.15

  (PTCDA). The results showed that the -CN group played an important role in increasing short circuit current density (I sc) and power conversion efficiency (PCE). Both rigid device glass-ITO/4T-CN/PTCDA/Al and flexible device PET-ITO (indium tin oxides coated with polyethylene terephthalate)/4T-CN/PTCDA/Al had greater I sc and PCE compared with rigid device glass-ITO/4T/PTCDA/Al. It was possible that the

  摘要 为开发具有良好性能特性的新型光伏材料和有机光伏器件，5-cyano-2,2':5',2"-terthiophene (3T-CN)和5-cyano-2,2':5合成了',2":5",2"'-四噻吩(4T-CN)。3T-CN 和 4T-CN 是具有介晶特性的供体-受体寡噻吩衍生物。研究了3T-CN和4T-CN的光伏性能。使用 3T-CN、4T-CN 和 3,4,9,10-苝四羧酸二酐 (PTCDA) 制造刚性和柔性光伏器件。结果表明，-CN基团在提高短路电流密度（I sc）和功率转换效率（PCE）方面发挥了重要作用。与刚性器件玻璃-ITO 相比，刚性器件玻璃-ITO/4T-CN/PTCDA/Al 和柔性器件 PET-ITO（涂有聚对苯二甲酸乙二醇酯的氧化铟锡）/4T-CN/PTCDA/Al 具有更高的 I sc 和 PCE /4T/PTCDA/铝。具有强吸电子特性的-CN基团和4T-C
• Syntheses and Properties of Oligothiophenes with Cyano and Hexyl Groups
  作者：Hiroshi Wada、Tomohiro Taguchi、Masanao Goto、Takuya Kambayashi、Takehiko Mori、Ken Ishikawa、Hideo Takezoe

  DOI：10.1246/cl.2006.280

  日期：2006.3

  Syntheses of new oligothiophenes which have cyano and hexyl groups at the ends of quarter- and ter-thiophenes are described. The observations of DSC and polarizing microscopy indicate the presence of liquid-crystalline (LC) phases over a wide temperature range. The energy gaps are discussed on the basis of the absorption and photoluminescence (PL) spectra and cyclic voltammetry. Thin films of oligothiophenes fabricated by vacuum deposition are investigated by AFM and XRD measurements.

  介绍了在四分之一噻吩和三噻吩末端带有氰基和己基的新型低聚噻吩的合成过程。DSC 和偏振显微镜的观察结果表明，在很宽的温度范围内都存在液晶（LC）相。根据吸收和光致发光（PL）光谱以及循环伏安法讨论了能隙问题。通过原子力显微镜 (AFM) 和 X 射线衍射 (XRD) 测量研究了通过真空沉积制造的低聚噻吩薄膜。
• Compromise between conjugation length and charge-transfer in nonlinear optical η5-monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands: Synthesis, electrochemical studies and first hyperpolarizabilities
  作者：M. Helena Garcia、Paulo J. Mendes、M. Paula Robalo、A. Romão Dias、Jochen Campo、Wim Wenseleers、Etienne Goovaerts

  DOI：10.1016/j.jorganchem.2007.03.023

  日期：2007.6

  series of η5-monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands of general formula [FeCp(P_P)(NCSC4H2}nNO2)][PF6] (P_P = dppe, (+)-diop; n = 1–3) has been synthesized and characterized. The electrochemical behaviour of the new compounds was explored by cyclic voltammetry. Quadratic hyperpolarizabilities (β) of the complexes with dppe coligands have been determined

  一个系统的一系列的η 5通式-monocyclopentadienyliron（II）配合物与取代的低聚噻吩腈配体[FeCp（P_P）（NC SC 4 ħ 2 } Ñ NO 2）] [PF 6 ]（P_P = DPPE，（ +）-diop；n  = 1-3）已合成并表征。通过循环伏安法研究了新化合物的电化学行为。已经通过在1.064和1.550μm的两个基本波长下的超瑞利散射（HRS）测量来确定具有DPPE大分子配体的二次超极化率（β），以揭示双光子共振效应并估计静态β价值观。将所得到的总的结果被发现是比用于相关η更好5 -monocyclopentadienyliron（II）络合物与p -苄腈衍生物。虽然增加了谐振的β在1.064微米与在共轭配体增加的噻吩单元的数目被发现（高达910×10 -30  ESU），静态值β 0保持几乎不变，如图中的1.550微米测量。结合电化学和光谱数据
• Phototoxic compounds for use as insect control agents
  申请人：Her Majesty the Queen as represented by the Minister of National Defense

  公开号：US05180838A1

  公开（公告）日：1993-01-19

  A method is provided herein for controlling insects which are harmful to agriculture and forestry and which are also harmful both to humans and to domestic animals. The method involves the steps of applying to a locus infested with such insects, a composition comprising a carrier and a biocidal-amount of a specifically-recited phototoxic, naturally-occurring thiophene, acetylene, or a synthetic, structurally-related derivative, analogue or acetylenic compound. Then, that composition, while at that locus, is subjected to UV radiation in the range about 300 nm to about 400 nm, for a sufficient time to impart, to such phototoxic naturally-occurring thiophene, acetylene, or synthetic, structurally-related derivative, analogue or acetylenic compound the desired insect control activity. Certain of these phototoxic naturally-occurring thiophenes, or acetylenes or synthetic, structurally-related compounds are also novel and provide novel insect control compositions.

  本文提供了一种用于控制对农林业有害、对人类和家畜也有害的昆虫的方法。该方法包括以下步骤：将一种组成物应用于被这种昆虫侵染的地点，该组成物包括载体和一种特定的光毒性、天然产生的噻吩、乙炔或合成的、结构相关的衍生物、类似物或乙炔化合物的生物杀虫剂量。然后，当该组成物在该地点时，将其暴露于300nm到400nm范围内的紫外辐射下，足够长的时间使得这种光毒性、天然产生的噻吩、乙炔或合成的、结构相关的衍生物、类似物或乙炔化合物具有所需的杀虫活性。其中一些光毒性、天然产生的噻吩或乙炔或合成的、结构相关的化合物也是新颖的，并提供了新颖的杀虫剂组成物。
• Drug delivery system for hydrophobic drugs
  申请人：QLT, Inc.

  公开号：EP1900357A2

  公开（公告）日：2008-03-19

  Compositions comprising microaggregates containing hydrophobic drugs, as well as methods for their production, are described. Such microaggregates may include micelle structures or combinations thereof with liposomes, and constitute an effective delivery vehicle for a hydrophobic agent. Methods for microaggregate production include the use of preferred lipid compounds and processing conditions favoring the production of small aggregates for improved filter sterilization.

  本文介绍了由含有疏水性药物的微团聚体组成的组合物及其生产方法。这种微团聚体可包括胶束结构或其与脂质体的组合，并构成疏水性药物的有效递送载体。微团聚体的生产方法包括使用优选的脂质化合物和有利于生产小团聚体的加工条件，以提高过滤灭菌效果。