5,5'-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-2,2'-bithiophene | 121846-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-2,2'-bithiophene
• 英文别名: 4,4'-([2,2'-Bithiophene]-5,5'-diyl)bis(2,6-di-tert-butylphenol)；2,6-ditert-butyl-4-[5-[5-(3,5-ditert-butyl-4-hydroxyphenyl)thiophen-2-yl]thiophen-2-yl]phenol
• CAS: 121846-89-7
• 化学式: C₃₆H₄₆O₂S₂
• 分子量: 574.892
• InChiKey: VLESHRDORBMYNS-UHFFFAOYSA-N

物化性质

• 沸点：
  601.7±55.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-2,2'-bithiophene 在 potassium hexacyanoferrate(III) 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 5,5'-bis(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-5,5'-dihydro-2,2'-bithiophene
  参考文献：
  名称：

  Tuning the Quinoid versus Biradicaloid Character of Thiophene-Based Heteroquaterphenoquinones by Means of Functional Groups

  摘要：

  A series of quinoidal bithiophenes (QBTs) with controlled variations in steric hindrance and electron activity of the substituents has been synthesized. Evidence of their quinoidal versus biradicaloid ground state electronic character has been experimentally detected and coherently identified as fingerprints by spectroscopic methods such as NMR, UV-vis, multiwavelength Raman. From this analysis, alkoxy groups have been shown to strongly affect the electronic structure and the ground-state energy and stability of QBTs. Quantum-chemical calculations correctly predict the experimental spectroscopic response, even while changing the alkyl on phenone from a tertiary carbon atom to secondary to primary toward an unsubstituted phenone, further confirming the validity of the approach proposed. A control of the electronic structure accompanied by negligible variations of the optical gap of the molecules has thus been demonstrated, extending the potential use of quinoidal species in fields ranging from photon harvesting to magnetic applications.

  DOI：

  10.1021/ja3072385
• 作为产物：
  描述：

  2-bromo-5-(3,5-di-tert-butyl-4-(trimethylsiloxy)phenyl)thiophene 在 四(三苯基膦)钯 、 正丁基锂 、 四丁基氟化铵 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.01h， 生成 5,5'-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-2,2'-bithiophene
  参考文献：
  名称：

  新型杂四苯醌的合成及其电化学，结构和光谱表征。

  摘要：

  新型杂四苯醌，5,5'-双（3,5-二叔丁基-4-氧代-2,5-环己二-1-亚基）-5,5'-二氢-2,2'-二苯基（3 ）及其2,2'-双亚乙烯基（4），2,2'-联呋喃基（5）和2,2'-bi-N-甲基吡咯基（6）类似物是通过逐步交叉偶联反应或通过更方便的杂环取代的酚的一锅氧化均偶联反应。尽管具有高度共轭扩展的体系，但醌3-6在固态和在普通有机溶剂中的溶液中非常稳定。这些醌经历可逆的一步两电子还原直至阴离子，再经历一步两电子氧化反应直至阳离子。这些醌的E（1）（红色）随着引入的杂环的芳香性的增加而增加。这些醌的E（1）（ox）似乎是由所掺入杂环的电离势确定的。因此，在醌3-6中，表现出最低的E（1）（ox）值的N-甲基醌6表现出最小的E（1）（sum）。通过X射线晶体学发现醌5以不寻常的O-顺式构型存在于固态，而醌3以S-反式构型存在于固态。顺式和反式异构体在3-5中可相互转化，而在（1）H

  DOI：

  10.1021/jo9600363

文献信息

• p-Diphenoquinone analogs extended by dihydrothiophenediylidene insertion. A novel amphoteric multistage redox system
  作者：Kazuko Takahashi、Tsuyoshi Suzuki

  DOI：10.1021/ja00196a075

  日期：1989.7

  Synthese et etude du comportement electrochimique de bis-[di-t-butyl-3,5 oxo-4 cyclohexadiene-1,5ylidene] ter- et quaterthiophenediylene ainsi que le derive bithiophenylidene-2,2'

  Synthese etude du comporementelectrochimique de bis-[di-t-butyl-3,5 oxo-4 cyclohexadiene-1,5ylidene] ter- et quaterthiophenediylene ainsi que le衍生联苯二亚苯基-2,2'
• Optical properties of a quinoid molecule
  作者：Franco D’Amore、Marta Lanata、Maria C. Gallazzi、Giuseppe Zerbi

  DOI：10.1016/s0009-2614(03)01152-7

  日期：2003.8

  We report on linear and third order nonlinear optical properties of the quinoid molecule 5,5'-bis(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadiene-1-ylidene)-5,5'-dihydro-2, T-bithiophene. Variable angle spectroscopic ellipsometry has been used to determine the dispersion of the dielectric in a spectral range from the near infrared to the near ultraviolet. We have measured a high value of the index of refraction in the transparency region (i.e., n = 1.886 at lambda = 1.5 mum), indicating the high polarisability of the molecule under study. The nonlinear optical properties have been measured by third harmonic generation in the near infrared spectral range. At lambda = 1.5 muM the nonlinear coefficient of the molecule has been estimated to be 4.2 x 10(-11) m(2)/V-2 (3.0 x 10(-11) esu). (C) 2003 Elsevier B.V. All rights reserved.
• Tuning the Quinoid versus Biradicaloid Character of Thiophene-Based Heteroquaterphenoquinones by Means of Functional Groups
  作者：Eleonora V. Canesi、Daniele Fazzi、Letizia Colella、Chiara Bertarelli、Chiara Castiglioni

  DOI：10.1021/ja3072385

  日期：2012.11.21

  A series of quinoidal bithiophenes (QBTs) with controlled variations in steric hindrance and electron activity of the substituents has been synthesized. Evidence of their quinoidal versus biradicaloid ground state electronic character has been experimentally detected and coherently identified as fingerprints by spectroscopic methods such as NMR, UV-vis, multiwavelength Raman. From this analysis, alkoxy groups have been shown to strongly affect the electronic structure and the ground-state energy and stability of QBTs. Quantum-chemical calculations correctly predict the experimental spectroscopic response, even while changing the alkyl on phenone from a tertiary carbon atom to secondary to primary toward an unsubstituted phenone, further confirming the validity of the approach proposed. A control of the electronic structure accompanied by negligible variations of the optical gap of the molecules has thus been demonstrated, extending the potential use of quinoidal species in fields ranging from photon harvesting to magnetic applications.
• Synthesis of Novel Heteroquaterphenoquinones and Their Electrochemical, Structural, and Spectroscopic Characterization
  作者：Kazuko Takahashi、Atsushi Gunji、Kazunori Yanagi、Misao Miki

  DOI：10.1021/jo9600363

  日期：1996.1.1

  cross-coupling reaction or by a more convenient one-pot oxidative homocoupling reaction of heterocycle-substituted phenols. Despite a highly conjugation-extended system, the quinones 3-6 are very stable in the solid state and in solution in common organic solvents. These quinones undergo a reversible one-stage, two-electron reduction up to dianions and a two-stage, one-electron oxidation reaction up to dications

  新型杂四苯醌，5,5'-双（3,5-二叔丁基-4-氧代-2,5-环己二-1-亚基）-5,5'-二氢-2,2'-二苯基（3 ）及其2,2'-双亚乙烯基（4），2,2'-联呋喃基（5）和2,2'-bi-N-甲基吡咯基（6）类似物是通过逐步交叉偶联反应或通过更方便的杂环取代的酚的一锅氧化均偶联反应。尽管具有高度共轭扩展的体系，但醌3-6在固态和在普通有机溶剂中的溶液中非常稳定。这些醌经历可逆的一步两电子还原直至阴离子，再经历一步两电子氧化反应直至阳离子。这些醌的E（1）（红色）随着引入的杂环的芳香性的增加而增加。这些醌的E（1）（ox）似乎是由所掺入杂环的电离势确定的。因此，在醌3-6中，表现出最低的E（1）（ox）值的N-甲基醌6表现出最小的E（1）（sum）。通过X射线晶体学发现醌5以不寻常的O-顺式构型存在于固态，而醌3以S-反式构型存在于固态。顺式和反式异构体在3-5中可相互转化，而在（1）H