1,12-Bis[3,5-di(tert-butyl)phenyl]-3,10-bis{[3,5-di(tert-butyl)phenyl]ethynyl}-4,9-bis[(triisopropylsilyl)ethynyl]-dodeca-3,9-diene-1,5,7,11-tetrayne | 373596-48-6

• 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: 1,12-Bis[3,5-di(tert-butyl)phenyl]-3,10-bis{[3,5-di(tert-butyl)phenyl]ethynyl}-4,9-bis[(triisopropylsilyl)ethynyl]-dodeca-3,9-diene-1,5,7,11-tetrayne
• 英文别名: [3-[1,5-Bis(3,5-ditert-butylphenyl)penta-1,4-diyn-3-ylidene]-11-(3,5-ditert-butylphenyl)-9-[2-(3,5-ditert-butylphenyl)ethynyl]-8-[2-tri(propan-2-yl)silylethynyl]undec-8-en-1,4,6,10-tetraynyl]-tri(propan-2-yl)silane；[3-[1,5-bis(3,5-ditert-butylphenyl)penta-1,4-diyn-3-ylidene]-11-(3,5-ditert-butylphenyl)-9-[2-(3,5-ditert-butylphenyl)ethynyl]-8-[2-tri(propan-2-yl)silylethynyl]undec-8-en-1,4,6,10-tetraynyl]-tri(propan-2-yl)silane
• CAS: 373596-48-6
• 化学式: C₉₄H₁₂₆Si₂
• 分子量: 1312.21
• InChiKey: HRZNPEAPZJSGIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.62
• 重原子数：
  96
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,12-Bis[3,5-di(tert-butyl)phenyl]-3,10-bis{[3,5-di(tert-butyl)phenyl]ethynyl}-4,9-bis[(triisopropylsilyl)ethynyl]-dodeca-3,9-diene-1,5,7,11-tetrayne 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  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：

  1,3-di-tert-butyl-5-ethynylbenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 四甲基乙二胺 、 氧气 、 potassium carbonate 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,12-Bis[3,5-di(tert-butyl)phenyl]-3,10-bis{[3,5-di(tert-butyl)phenyl]ethynyl}-4,9-bis[(triisopropylsilyl)ethynyl]-dodeca-3,9-diene-1,5,7,11-tetrayne
  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