3-(4-tert-butylphenoxy)phthalonitrile | 201480-81-1

• 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: 3-(4-tert-butylphenoxy)phthalonitrile
• 英文别名: 3-(4-tert-butylphenoxy)benzene-1,2-dicarbonitrile
• CAS: 201480-81-1
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: RTLLIMBAAJJMLB-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C(Solv: toluene (108-88-3))
• 沸点：
  420.6±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-(4-tert-butylphenoxy)phthalonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以47%的产率得到tetra(α-4-tert-butylphenoxy)phthalocyanine
  参考文献：
  名称：

  无金属酞菁的轻度温和合成

  摘要：

  对于酞菁化合物的合成和研究而言，重要的是这些化合物在低温下容易获得。我们观察到，在室温下用于合成酞菁前体的简单系统中有时会发现不含金属的酞菁，进一步的研究表明，在低温下有效形成酞菁的关键在于存在等体积的醇和胺在反应体系中，除了底物邻苯二甲腈和溶剂。提出了一种合成机理并实现了简便的合成，例如在温和的温度下由相应的取代邻苯二甲腈合成四-α（β）-硝基酞菁和四-α（β）-（4-叔丁基苯氧基）酞菁（ 37°C）。

  DOI：

  10.1055/a-1499-8865
• 作为产物：
  描述：

  4-叔丁基苯酚 、 3-硝基邻苯二腈 在 lithium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以78%的产率得到3-(4-tert-butylphenoxy)phthalonitrile
  参考文献：
  名称：

  几种可溶性四苯氧基取代铜锌酞菁的合成与表征

  摘要：

  描述了带有苯氧基取代基的铜和锌酞菁 (Pcs) 的合成。制备 Pcs 9-16 所需的前体是通过空间位阻酚衍生物与 4-硝基邻苯二甲腈 (1) 或 3-硝基邻苯二甲腈 (2) 之间的亲核芳族取代反应制备的。得到的前体邻苯二甲腈在 DMAE 或 DBU 催化的 pentan-1-ol 中的环四聚得到所需的 Pcs，它们很好地溶于常见的有机溶剂，如氯仿和二氯甲烷。这些 Pcs 中的每一个都由四种结构异构体组成，并通过 1H NMR、UV/Vis、IR 和质谱以及元素分析进行​​表征，与所提出的结构一致。

  DOI：

  10.1055/s-2005-861795

文献信息

• 两种铜钛菁金属有机配合物及其制备方法
  申请人：沈阳化工大学

  公开号：CN106565722A

  公开（公告）日：2017-04-19

  两种铜钛菁金属有机配合物及其制备方法，涉及两种配合物及其制备方法，本发明公开了两种新型铜钛菁有机配合物的制备方法及其在碳氮偶联反应的催化应用。该方法涉及金属有机化学、配位化学和催化领域。本发明中的两种金属有机配合物是以3‑烷氧基取代的邻苯二腈和3‑芳氧基取代的邻苯二腈为配体，与铜盐反应制备得到两个四取代的铜酞菁配合物，对配合物进行了核磁、质谱、红外、紫外测试表征。结果表明，两种配合物结构明确。将其应用于碳氮偶联反应的催化应用研究中发现，该类配合物催化碳氮偶联反应时，具有反应条件温和，后处理简单，催化活性高、选择性高的良好特性，是极具潜力的催化剂。
• Intramolecular aggregation and optical limiting properties of triazine-linked mono-, bis- and tris-phthalocyanines
  作者：Jun Chen、Tao Zhang、Shuangqing Wang、Rui Hu、Shayu Li、Jin Shi Ma、Guoqiang Yang

  DOI：10.1016/j.saa.2015.04.093

  日期：2015.10

  A series of triazine-linked mono-, bis- and tris-phthalocyanines are synthesized, intramolecular aggregation is found in bis- and tris-phthalocyanines via pi-pi stacking interaction. Theoretical and experimental studies reveal the formation of the intramolecular aggregation. The spectrographic, photophysical and nonlinear optical properties of these compounds are adjusted for the formation of the intramolecular aggregation. The bis-phthalocyanine dimer presents smaller fluorescence quantum yield, lower triplet formation yield and the triplet-minus-ground state extinction coefficient, which causes poorer optical limiting performance. It is interesting that the tris-phthalocyanine is composed of a mono-phthalocyanine part and a bis-phthalocyanine part, the optical limiting property of the tris-phthalocyanine is similar to that of mono-phthalocyanine. (C) 2015 Elsevier B.V. All rights reserved.
• 宽光谱带的近红外吸收染料
  申请人：上海昀通电子科技有限公司

  公开号：CN113136112B

  公开（公告）日：2023-04-28
• Synthesis and electrochemical characterisation of α- and β-tetra-substituted oxo(phthalocyaninato) titanium(IV) complexes
  作者：Prudence Tau、Tebello Nyokong

  DOI：10.1016/j.poly.2005.11.025

  日期：2006.5

  The synthesis, spectroscopic and electrochemical characterisation of the following oxotitanium tetra-substituted phthalocyanines are reported: 1,(4)-(tetraphenoxyphthalocyaninato)titanium(IV) oxide (5a); 1,(4) -(tetra- tert-butylphenoxyphthalocyaninato) titanium(IV) oxide (5b); 2,(3)-(tetraphenoxyphthalocyaninato)titanium(IV) oxide (6a) and 2,(3)-(tetra-tert-butylphenoxyphthalocyaninato)titanium(IV) oxide (6b). Complexes 5a and 5b are substituted at the non-peripheral (a) positions, whereas complexes 6a and 6b are substituted at the peripheral (P) positions. Cyclic voltammograms of all four complexes are similar, with three reversible reduction couples and three quasi-reversible to irreversible oxidations. The first two reductions are two-electron processes, confirmed by spectroelectrochemistry to be due to (TiPc-2)-Pc-IV/(TiPc-3)-Pc-II and (TiPc-2)-Pc-II/(TiPc-3)-Pc-1 redox processes. Spectroelectrochemistry showed that upon oxidation, the molecule decomposes. Oxidation is expected to occur at the ring. Chronocoulometry confirmed two electron transfer at the first and second reduction steps; and a one electron transfer at the third reduction. (C) 2005 Elsevier Ltd. All rights reserved.
• Synthesis, fluorescence, excited triplet state properties and singlet oxygen generation of para-(tert-butylphenoxy) substituted phthalocyanines containing group IV A central elements
  作者：Xian-Fu Zhang、Xiaona Shao、Hongyan Tian、Xiaojie Sun、Kaixue Han

  DOI：10.1016/j.dyepig.2013.06.010

  日期：2013.11

  Phthalocyanines containing group IV A central elements and non-peripheral para-(tert-butyl)-phenoxy substituents, i.e. M(OH)(2)PC(alpha-t-butyl-phenoxy)(4) (M is Si, Ge, Sn and Pb respectively), were synthesized. The effects of the central elements on the photosensitizing and photophysical properties (quantum yield of singlet oxygen formation, quantum yield and lifetime of lowest lying excited triplet- and singlet state) were investigated by laser flash photolysis, time correlated single photon counting, steady state fluorescence and absorption spectra. The incorporation of large atoms significantly enhances the efficiency of excited triplet state and singlet oxygen formation. The triplet quantum yield is increased 2.5 times to 0.75 for the lead tetrasubstituted phthalocyanine relative to that of 0.30 determined for the silyl analog, while the triplet lifetime is longer than 120 mu s. Correspondingly, the quantum yield of singlet oxygen formation is 0.64 for the lead tetrasubstituted phthalocyanine and is 0.26 for the silyl compound. All of the PC complexes maintain reasonably good fluorescence characteristics with the shortest fluorescence lifetime measured being 3.14 ns, and the lowest fluorescence quantum yield of 0.18. These properties indicate that some of the PC complexes may be good candidates for singlet oxygen photosensitization. (C) 2013 Elsevier Ltd. All rights reserved.