1,4-bis-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylbenzene

• 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: 1,4-bis-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylbenzene
• 英文别名: 4-[2-[4-[2-(4-Carboxyphenyl)ethynyl]-2,5-dihexylphenyl]ethynyl]benzoic acid；4-[2-[4-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylphenyl]ethynyl]benzoic acid
• 化学式: C₃₆H₃₈O₄
• 分子量: 534.695
• InChiKey: HMWAZZJCWQSHDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二乙基甲酰胺 、 zinc(II) nitrate hexahydrate 、 1,4-bis-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylbenzene 以 水 为溶剂， 以44%的产率得到(Zn(1,4-bis-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylbenzene)(N,N-diethylformamide)2)
  参考文献：
  名称：

  One-dimensional Zn(II) oligo(phenyleneethynylene)dicarboxylate coordination polymers: Synthesis, crystal structures, thermal and photoluminescent properties

  摘要：

  The rigid, p-conjugated dicarboxylic acid 1,4-bis-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylbenzene {HO2C[PEP(hexyl)(2)EP]CO2H} has been used to synthesise the new crystalline coordination polymers {Zn(O2C[PEP(hexyl)(2)EP]CO2)(DMF)(2)} (1) and {Zn(O2C[PEP(hexyl)(2)EP]CO2)(DEF)(2)} (2) in N, N-dimethylformamide (DMF) and N, N-diethylformamide (DEF), respectively, under mild conditions. Single-crystal X-ray crystallography revealed that 1 and 2 are isostructural and consist of uncharged zigzag coordination chains in which [Zn(formamide)(2)](2+) fragments are bridged by (O2C[PEP(hexyl)(2)EP] CO2)(2) ligands. The zigzag chains possess different intra-chain Zn center dot center dot center dot Zn center dot center dot center dot Zn angles due to the different volumes of the coordinating formamide molecules and subtle differences in the hydrophobic inter-chain interactions. Upon heating 1 and 2 to 200 degrees C, removal of the coordinating formamide molecules occurs, yielding the formamide-free compounds 1-DMF and 2-DEF of composition {Zn(O2C[PEP(hexyl)(2)EP] CO2)}. According to powder X-ray diffraction and FT-IR spectroscopy studies, these materials are not crystalline but still possess partial ordering of intact, yet modified coordination chains in a structural arrangement which appears to be related to the respective parent compounds. Compounds 1, 2, 1-DMF and 2-DEF exhibit blue photoluminescence. The emission maxima of 1-DMF and 2-DEF are red-shifted by ca. 25 nm with respect to lambda(max) of 1 and 2, respectively. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.04.004
• 作为产物：
  描述：

  4-(4-Ethynyl-2,5-dihexyl-phenylethynyl)-benzoic acid methyl ester 在 哌啶 、 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1,4-bis-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylbenzene
  参考文献：
  名称：

  Hybrid Composites of Monodisperse π-Conjugated Rodlike Organic Compounds and Semiconductor Quantum Particles

  摘要：

  Composite materials of quantum particles (Q-particles) arranged in layers within crystalline powders of pi-conjugated, rodlike dicarboxylic acids are reported. The synthesis of the composites, either as three-dimensional crystals or as thin films at the air-water interface, comprises a two-step process: 1) The preparation of the Cd salts 6(Cd), 8(Cd) or Pb salts 6(Pb), 8(Pb) of the oligo(p-phenyteneethynytene)dicarboxylic acids 6(H), 8(H), in which the metal ions are arranged in ribbons and are separated by the long axis of the organic molecules, as demonstrated by X-ray powder diffraction analysis of the solids and grazing incidence X-ray diffraction analysis of the films on water. 2) Topotactic solid/gas reaction of these salts with H2S to convert the metal ions into Q-particles of CdS or PbS embedded in the organic matrix that consists of the acids 6(H) and 8(H). These hybrid materials have been characterized by X-ray photoelectron spectroscopy and transmission electron microscopy.

  DOI：

  10.1002/1521-3765(20020315)8:6<1413::aid-chem1413>3.0.co;2-6

文献信息

• One-dimensional Zn(II) oligo(phenyleneethynylene)dicarboxylate coordination polymers: Synthesis, crystal structures, thermal and photoluminescent properties
  作者：Andreas Schaate、Miriam Schulte、Michael Wiebcke、Adelheid Godt、Peter Behrens

  DOI：10.1016/j.ica.2009.04.004

  日期：2009.8

  The rigid, p-conjugated dicarboxylic acid 1,4-bis-[2-(4-carboxyphenyl)ethynyl]-2,5-dihexylbenzene HO2C[PEP(hexyl)(2)EP]CO2H} has been used to synthesise the new crystalline coordination polymers Zn(O2C[PEP(hexyl)(2)EP]CO2)(DMF)(2)} (1) and Zn(O2C[PEP(hexyl)(2)EP]CO2)(DEF)(2)} (2) in N, N-dimethylformamide (DMF) and N, N-diethylformamide (DEF), respectively, under mild conditions. Single-crystal X-ray crystallography revealed that 1 and 2 are isostructural and consist of uncharged zigzag coordination chains in which [Zn(formamide)(2)](2+) fragments are bridged by (O2C[PEP(hexyl)(2)EP] CO2)(2) ligands. The zigzag chains possess different intra-chain Zn center dot center dot center dot Zn center dot center dot center dot Zn angles due to the different volumes of the coordinating formamide molecules and subtle differences in the hydrophobic inter-chain interactions. Upon heating 1 and 2 to 200 degrees C, removal of the coordinating formamide molecules occurs, yielding the formamide-free compounds 1-DMF and 2-DEF of composition Zn(O2C[PEP(hexyl)(2)EP] CO2)}. According to powder X-ray diffraction and FT-IR spectroscopy studies, these materials are not crystalline but still possess partial ordering of intact, yet modified coordination chains in a structural arrangement which appears to be related to the respective parent compounds. Compounds 1, 2, 1-DMF and 2-DEF exhibit blue photoluminescence. The emission maxima of 1-DMF and 2-DEF are red-shifted by ca. 25 nm with respect to lambda(max) of 1 and 2, respectively. (C) 2009 Elsevier B. V. All rights reserved.
• Hybrid Composites of Monodisperse π-Conjugated Rodlike Organic Compounds and Semiconductor Quantum Particles
  作者：Volker Hensel、Adelheid Godt、Ronit Popovitz-Biro、Hagai Cohen、Torben R. Jensen、Kristian Kjaer、Isabelle Weissbuch、Efrat Lifshitz、Meir Lahav

  DOI：10.1002/1521-3765(20020315)8:6<1413::aid-chem1413>3.0.co;2-6

  日期：2002.3.15

  Composite materials of quantum particles (Q-particles) arranged in layers within crystalline powders of pi-conjugated, rodlike dicarboxylic acids are reported. The synthesis of the composites, either as three-dimensional crystals or as thin films at the air-water interface, comprises a two-step process: 1) The preparation of the Cd salts 6(Cd), 8(Cd) or Pb salts 6(Pb), 8(Pb) of the oligo(p-phenyteneethynytene)dicarboxylic acids 6(H), 8(H), in which the metal ions are arranged in ribbons and are separated by the long axis of the organic molecules, as demonstrated by X-ray powder diffraction analysis of the solids and grazing incidence X-ray diffraction analysis of the films on water. 2) Topotactic solid/gas reaction of these salts with H2S to convert the metal ions into Q-particles of CdS or PbS embedded in the organic matrix that consists of the acids 6(H) and 8(H). These hybrid materials have been characterized by X-ray photoelectron spectroscopy and transmission electron microscopy.