4-[4-(triphenylmethyl)phenoxy]-1,2-dicyanobenzene | 356082-19-4

• 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-(triphenylmethyl)phenoxy]-1,2-dicyanobenzene
• 英文别名: 4-(p-triphenylmethylphenoxy)-1,2-dicyanobenzene；4-(p-triphenylmethylphenoxy)phthalonitrile；4-(4-tritylphenoxy)phthalonitrile；4-(4-tritylphenoxy)benzene-1,2-dicarbonitrile
• CAS: 356082-19-4
• 化学式: C₃₃H₂₂N₂O
• 分子量: 462.55
• InChiKey: GLCWESUUGMBUNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[4-(triphenylmethyl)phenoxy]-1,2-dicyanobenzene 在 sodium methylate 、 氨 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以55.5%的产率得到4-(p-triphenylmethylphenoxy)isoindoline-1,3-diimine
  参考文献：
  名称：

  Synthesis and spectral properties of meso-phenyltetrabenzoazaporphyrins containing triphenylmethyl groups

  摘要：

  4-(p-Triphenylmethylphenoxy)isoindoline-1,3-diimine was synthesized starting from 4-(p-triphenylmethylphenoxy)phthalodinitrile obtained by the reaction of 4-nitrophthalodinitrile with 4-(triphenylmethyl)phenol. The former was reacted with phenylacetic acid in the presence of zinc oxide to obtain zinc complexes of meso-phenyltetrabenzoazaporphyrins containing triphenylmethyl groups. Spectral properties of the synthesized compounds were studied.

  DOI：

  10.1134/s107036320807027x
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 三苯甲基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70.5%的产率得到4-[4-(triphenylmethyl)phenoxy]-1,2-dicyanobenzene
  参考文献：
  名称：

  Synthesis, mesomorphism and electrochemical properties of tetrasubstituted zinc and copper phthalocyanines

  摘要：

  我们描述了具有液晶特性的高溶解度四取代锌和铜酞菁的合成。使用元素分析、MS、1H-NMR、FTIR 和 UV-Vis 吸收光谱对这些化合物进行了表征。通过偏光光学显微镜和差示扫描量热法研究了酞菁（Pcs）的液晶性质。所有四种化合物均表现出热致柱状中间相，其中两种化合物表现出明显的六方有序性。此外，这些个人电脑表现出溶致行为。澄清温度高于 300 °C，冷却时中间相可以“冻结”成玻璃态。这些酞菁的循环伏安研究显示出电化学稳定性和可逆氧化还原行为。配体中没有任何偶氮基团的PCs表现出可逆的氧化和还原，而具有偶氮基团的PCs仅表现出可逆的还原步骤。根据氧化电位计算，HOMO 能量值约为 5 eV，这使得这些化合物作为 p 型有机半导体在电光应用中颇受关注。

  DOI：

  10.1039/b821306b

文献信息

• Mesomorphism and Glass Formation of Phthalocyanine Metal Complexes with Bulky Substituents
  作者：N. Usol'tseva、V. Bykova、G. Ananjeva、N. Zharnikova、E. Kudrik

  DOI：10.1080/15421400490435350

  日期：2004.1

  ultraviolet-visible (UV-VIS) and infrared (IR) spectroscopy and their phase transitions were studied by polarizing optical microscopy. Some of these complexes exhibit enantiotropic mesomorphic properties and transition into glass state on cooling. The glass appearance is influenced not only by side chains’ structure, but also by the nature of metal.

  本文涉及酞菁配合物的合成，该配合物含有四种低聚（氧乙烯）-、氧苯-、对羟基苯甲酸的酯或对羟基偶氮苯侧链，以庞大的三苯甲基取代基封端。它们的纯度是通过柱色谱法和令人满意的元素分析确定的。通过核磁共振 (NMR)、快速原子轰击质谱 (FAB-MS)、紫外-可见 (UV-VIS) 和红外 (IR) 光谱表征所得酞菁的结构，并通过偏光显微镜研究它们的相变. 这些配合物中的一些表现出对映性介晶性质并在冷却时转变为玻璃态。玻璃外观不仅受侧链结构的影响，还受金属性质的影响。
• Flying-seed-like liquid crystals 2: unprecedented guidelines to obtain liquid crystalline compounds
  作者：Yasufumi Takagi、Kazuchika Ohta、Shota Shimosugi、Tatsuya Fujii、Eiji Itoh

  DOI：10.1039/c2jm32284f

  日期：——

  In order to obtain novel “flying-seed-like” liquid crystals, we have prepared a series of bulky group-substituted phthalocyanine derivatives without any long alkyl chains: tetra[4-(triphenylmethyl)-phenoxy]phthalocyaninato copper(II) (1a), tetra[4-(1,1-diphenylethyl)phenoxy]phthalocyaninato copper(II) (1b), tetra[4-(1-methyl-1-phenylethyl)phenoxy]phthalocyaninato copper(II) (1c), tetra[4-(tert-butyl)phenoxy]phthalocyaninato copper(II) (1d), and octa[4-(triphenylmethyl)phenoxy]phthalocyaninato copper(II) (4). We have established by using a polarizing optical microscope, a differential scanning calorimeter and a temperature-dependent small angle X-ray diffractometer that the Pc derivatives 1a–d, but not 4, show columnar mesomorphism from r.t. to the extremely high decomposition temperatures at 450–500 °C. Their mesomorphism originates from thermal fluctuations due to free rotation of the bulky substituents. Thus, we have systematically demonstrated for the first time that liquid crystals can be also obtained by a series of novel bulky substituents instead of conventional long alkyl chains. Hence, we will be able to obtain a wide variety of new liquid crystalline compounds by using these bulky substituents instead of long alkyl chains. Very interestingly, these are unprecedented guidelines to obtain liquid crystalline compounds.

  为了获得新颖的 "飞籽状 "液晶，我们制备了一系列没有长烷基链的笨重基团取代型酞菁衍生物：四[4-(三苯甲基)-苯氧基]酞菁铜(II) (1a)、四[4-(1,1-二苯基乙基)苯氧基]酞菁铜(II) (1b)、四[4-(1-甲基-1-苯基乙基)苯氧基]酞菁铜(II) (1c)、四[4-(叔丁基)苯氧基]酞菁铜(II) (1d) 和八[4-(三苯甲基)苯氧基]酞菁铜(II) (4)。我们利用偏光光学显微镜、差示扫描量热仪和随温度变化的小角 X 射线衍射仪确定，酞菁铜衍生物 1a-d （而非 4）在 450-500 °C 的极高分解温度下呈现柱状介形。它们的介形性源于笨重取代基自由旋转引起的热波动。因此，我们首次系统地证明，用一系列新颖的笨重取代基代替传统的长烷基链也能获得液晶。因此，通过使用这些大块取代基代替长烷基链，我们将能够获得各种各样的新型液晶化合物。有趣的是，这些都是获得液晶化合物的前所未有的准则。
• Synthesis, mesomorphism and electrochemical properties of tetrasubstituted zinc and copper phthalocyanines
  作者：N. Zharnikova、N. Usol'tseva、E. Kudrik、M. Thelakkat

  DOI：10.1039/b821306b

  日期：——

  We describe the synthesis of highly soluble, tetrasubstituted zinc and copper phthalocyanines exhibiting liquid crystalline properties. These compounds were characterized using elemental analysis, MS, 1H-NMR, FTIR and UV-Vis absorption spectroscopy. The liquid crystalline properties of phthalocyanines (Pcs) were studied by polarizing optical microscopy and differential scanning calorimetry. All of the four compounds exhibit thermotropic columnar mesophases and two of them show clear hexagonal ordering. Additionally, these Pcs display lyotropic behaviour. The clearing temperatures lie above 300 °C and on cooling down the mesophase can be “frozen” into a glassy state. The cyclic voltammetry studies of these phthalocyanines show electrochemical stability and reversible redox behaviour. The Pcs without any azo groups in the ligands exhibit both reversible oxidation and reduction, whereas those with azo groups show only reversible reduction steps. The low HOMO energy values of about 5 eV as calculated from oxidation potential make these compounds interesting as p-type organic semiconductors for electro-optical applications.

  我们描述了具有液晶特性的高溶解度四取代锌和铜酞菁的合成。使用元素分析、MS、1H-NMR、FTIR 和 UV-Vis 吸收光谱对这些化合物进行了表征。通过偏光光学显微镜和差示扫描量热法研究了酞菁（Pcs）的液晶性质。所有四种化合物均表现出热致柱状中间相，其中两种化合物表现出明显的六方有序性。此外，这些个人电脑表现出溶致行为。澄清温度高于 300 °C，冷却时中间相可以“冻结”成玻璃态。这些酞菁的循环伏安研究显示出电化学稳定性和可逆氧化还原行为。配体中没有任何偶氮基团的PCs表现出可逆的氧化和还原，而具有偶氮基团的PCs仅表现出可逆的还原步骤。根据氧化电位计算，HOMO 能量值约为 5 eV，这使得这些化合物作为 p 型有机半导体在电光应用中颇受关注。
• Synthesis and Spectral Characteristics of Unsymmetrical Porphirazines with Triphrnylmethyl Groups
  作者：N. E. Galanin、E. V. Kudrik、G. P. Shaposhnikov、V. V. Aleksandriiskii

  DOI：10.1023/b:rujo.0000043721.15447.13

  日期：2004.5

  Condensation of 4-(p-triphenylmethylphenoxy)- 1,2-dicyanobenzene with 1,2-di(methylthio)maledinitrile or 2,3-dicyano-5,6-diphenylpyrazine afforded symmetric and unsymmetrical porphirazines. The effect of their structural modification on the spectral characteristics was investigated.
• Synthesis and properties of [4′-(p-triphenylmethylphenoxy)-7,8:12,13:17,18-tribenzoporphyrazinato]nickel(II)
  作者：Yulia V. Romanenko、Elena A. Danilova、Olga G. Khelevina、Mikhail K. Islyaikin

  DOI：10.1016/j.mencom.2008.03.009

  日期：2008.3

  A new noncentrosymmetric structural analogue of phthalocyanine, [4'-(p-triphenylmethylphenoxy)-7,8:12,13:17,18-tribenzoporphyrazinato]nickel(11), was obtained by the condensation of 3,5-bis(1-imino-3-isoindolinylidenamino)-1,2,4-triazole in the presence of Ni(OAc)(2)center dot 4H(2)O or a Ni complex of 3,5-bis(1-imino-3-isoindolinylidenamino)-1,2,4-triazole with 4-(p-triphenylmethylphenoxy)phthalonitrile.