5-[[4-[4-[5-[5-[5-[1-[4-[[3,5-bis[C-hydroxy-N-[6-(1-hydroxyoctylideneamino)pyridin-2-yl]carbonimidoyl]phenyl]carbamoyl]phenyl]triazol-4-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]triazol-1-yl]benzoyl]amino]-1-N,3-N-bis[6-(1-hydroxyoctylideneamino)pyridin-2-yl]benzene-1,3-dicarboximidic acid | 1250264-19-7

• 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: 5-[[4-[4-[5-[5-[5-[1-[4-[[3,5-bis[C-hydroxy-N-[6-(1-hydroxyoctylideneamino)pyridin-2-yl]carbonimidoyl]phenyl]carbamoyl]phenyl]triazol-4-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]triazol-1-yl]benzoyl]amino]-1-N,3-N-bis[6-(1-hydroxyoctylideneamino)pyridin-2-yl]benzene-1,3-dicarboximidic acid
• CAS: 1250264-19-7
• 化学式: C₉₈H₁₀₄N₂₀O₁₀S₃
• 分子量: 1818.23
• InChiKey: CKDQKPKHZKNLJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.9
• 重原子数：
  131
• 可旋转键数：
  46
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  517
• 氢给体数：
  10
• 氢受体数：
  29

反应信息

• 作为产物：
  描述：

  5-((4-azidobenzoyl)amino)-N,N'-bis(6-(octanoylamino)pyridine-2-yl)isophthalamide 、 5,5''-diethynyl-2,2':5',2''-terthiophene 在 溴化三(三苯基磷)铜 、 N,N-二异丙基乙胺 、 copper(I) bromide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 0.5h， 以14 mg的产率得到5-[[4-[4-[5-[5-[5-[1-[4-[[3,5-bis[C-hydroxy-N-[6-(1-hydroxyoctylideneamino)pyridin-2-yl]carbonimidoyl]phenyl]carbamoyl]phenyl]triazol-4-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]triazol-1-yl]benzoyl]amino]-1-N,3-N-bis[6-(1-hydroxyoctylideneamino)pyridin-2-yl]benzene-1,3-dicarboximidic acid
  参考文献：
  名称：

  Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.10.096

文献信息

• 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 /
• 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.