4-{4-[(11-(4-Iodophenoxy)undecyl)oxy]phenyl}benzonitrile | 373596-54-4

• 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-[(11-(4-Iodophenoxy)undecyl)oxy]phenyl}benzonitrile
• CAS: 373596-54-4
• 化学式: C₃₀H₃₄INO₂
• 分子量: 567.51
• InChiKey: IFBBQWMUYUSCRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  34.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-{4-[(11-(4-Iodophenoxy)undecyl)oxy]phenyl}benzonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide (i-Pr)2N 、 四丁基氟化铵 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-(4-{[11-(4-Ethynylphenoxy)undecyl]oxy}phenyl)benzonitrile
  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'-(11-hydroxyundecyloxy)-4-cyanobiphenyl 在 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 4-{4-[(11-(4-Iodophenoxy)undecyl)oxy]phenyl}benzonitrile
  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

文献信息

• Highly Functionalized Dimeric Tetraethynylethenes and Expanded Radialenes: Strong Evidence for Macrocyclic Cross-Conjugation
  作者：Mogens Brøndsted Nielsen、Martin Schreiber、Yong Gu Baek、Paul Seiler、Steve Lecomte、Corinne Boudon、Rik R. Tykwinski、Jean-Paul Gisselbrecht、Volker Gramlich、Philip J. Skinner、Christian Bosshard、Peter Günter、Maurice Gross、François Diederich

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

  日期：2001.8.3

  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.