4',4'''-(((((3-(penta-1,4-diyn-3-ylidene)penta-1,4-diyne-1,5-diyl)bis(4,1-phenylene))bis(oxy))bis(undecane-11,1-diyl))bis(oxy))bis(([1,1'-biphenyl]-4-carbonitrile)) | 691869-71-3

• 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: 4',4'''-(((((3-(penta-1,4-diyn-3-ylidene)penta-1,4-diyne-1,5-diyl)bis(4,1-phenylene))bis(oxy))bis(undecane-11,1-diyl))bis(oxy))bis(([1,1'-biphenyl]-4-carbonitrile))
• CAS: 691869-71-3
• 化学式: C₇₀H₇₀N₂O₄
• 分子量: 1003.34
• InChiKey: IPNLNNCODCOBGA-UHFFFAOYSA-N

物化性质

• 沸点：
  990.5±65.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.67
• 重原子数：
  76.0
• 可旋转键数：
  30.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.5
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4',4'''-(((((3-(penta-1,4-diyn-3-ylidene)penta-1,4-diyne-1,5-diyl)bis(4,1-phenylene))bis(oxy))bis(undecane-11,1-diyl))bis(oxy))bis(([1,1'-biphenyl]-4-carbonitrile)) 在 吡啶 、 copper diacetate 、 氧气 作用下， 以 苯 为溶剂， 反应 24.0h， 以4%的产率得到5,10,15-Tris-{3-(4-{11-[4-(4-cyanophenyl)phenoxy]undecyloxy}phenyl)-1-[2-(4-{11-[4-(4-cyanophenyl)phenoxy]undecyloxy}phenyl)ethynyl]prop-2-ynylidene}cyclopentadeca-1,3,6,8,11,13-hexayne
  参考文献：
  名称：

  Highly Functionalized Dimeric Tetraethynylethenes and Expanded Radialenes: Strong Evidence for Macrocyclic Cross-Conjugation

  摘要：

  A selection of dimeric tetra-ethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X-ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5-di(tert-butyl)phenyl substituents, is presented. This macrocycle, the all-carbon core of which is isomeric with fullerene C-60, adopts a non-planar, "chair-like" conformation. Also a TEE dimer, carrying NN-dimethylaniline donor substituents, has been subjected to an X-ray crystallo graphic analysis. The electronic properties were studied by UV/Vis spectroscopy and electrochemistry, providing fundamental insight into mechanisms of pi -electron delocalization in the acyclic and macrocyclic chromophores. Donor or donor-acceptor-substituted dimeric TEE derivatives show very strong absorptions extending over the entire UV/Vis region; their longest wavelength absorption bands have high charge-transfer character. Macrocyclic cross-conjugation in the expanded radialenes becomes increasingly efficient with increasing donor-acceptor polarization. A dual, strongly solvent-polarity-dependent fluorescence was observed for a tetrakis(NN-dimethylaniline)-substituted dimeric TEE; this interesting emission behavior is explained by the twisted intramolecular charge-transfer (TICT) state model. Donor-substituted expanded radialenes display huge resonance-enhanced third-order nonlinear optical coefficients.

  DOI：

  10.1002/1521-3765(20010803)7:15<3263::aid-chem3263>3.0.co;2-3
• 作为产物：
  描述：

  4,4'-{1-[2-(Triisopropylsilyl)ethynyl]-3-[(triisopropylsilyl)prop-2-ynylidene]methylenebis[ethyne-1,2-diyl-4-phenyleneoxyundecamethylenoxy(4-phenylene)]}dibenzonitrile 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到4',4'''-(((((3-(penta-1,4-diyn-3-ylidene)penta-1,4-diyne-1,5-diyl)bis(4,1-phenylene))bis(oxy))bis(undecane-11,1-diyl))bis(oxy))bis(([1,1'-biphenyl]-4-carbonitrile))
  参考文献：
  名称：

  Highly Functionalized Dimeric Tetraethynylethenes and Expanded Radialenes: Strong Evidence for Macrocyclic Cross-Conjugation

  摘要：

  A selection of dimeric tetra-ethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X-ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5-di(tert-butyl)phenyl substituents, is presented. This macrocycle, the all-carbon core of which is isomeric with fullerene C-60, adopts a non-planar, "chair-like" conformation. Also a TEE dimer, carrying NN-dimethylaniline donor substituents, has been subjected to an X-ray crystallo graphic analysis. The electronic properties were studied by UV/Vis spectroscopy and electrochemistry, providing fundamental insight into mechanisms of pi -electron delocalization in the acyclic and macrocyclic chromophores. Donor or donor-acceptor-substituted dimeric TEE derivatives show very strong absorptions extending over the entire UV/Vis region; their longest wavelength absorption bands have high charge-transfer character. Macrocyclic cross-conjugation in the expanded radialenes becomes increasingly efficient with increasing donor-acceptor polarization. A dual, strongly solvent-polarity-dependent fluorescence was observed for a tetrakis(NN-dimethylaniline)-substituted dimeric TEE; this interesting emission behavior is explained by the twisted intramolecular charge-transfer (TICT) state model. Donor-substituted expanded radialenes display huge resonance-enhanced third-order nonlinear optical coefficients.

  DOI：

  10.1002/1521-3765(20010803)7:15<3263::aid-chem3263>3.0.co;2-3