(E,E)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl | 120926-78-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl
• 英文别名: 4,4'-bis(3,5-di-tert-butylstyryl)biphenyl；1,3-ditert-butyl-5-[(E)-2-[4-[4-[(E)-2-(3,5-ditert-butylphenyl)ethenyl]phenyl]phenyl]ethenyl]benzene
• CAS: 120926-78-5
• 化学式: C₄₄H₅₄
• 分子量: 582.913
• InChiKey: RZUYSQBPYIOENX-WXUKJITCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (E,E)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl 在 lithium 作用下， 以 氘代四氢呋喃 为溶剂， 生成 monolithium mono(2,2'-([1,1'-biphenyl]-4,4'-diyl)bis(1-(3,5-di-tert-butylphenyl)ethane-1,2-diide))
  参考文献：
  名称：

  Schenk,Rainer; Hucker, Joachim; Hopf, Henning, Angewandte Chemie, 1989, vol. 101, # 7, p. 942 - 944

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z,E)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl 在 2,3-丁二酮 作用下， 生成 (E,E)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl
  参考文献：
  名称：

  Triplet state 1- and 2-fold cis-trans isomerization of bis(styryl)arenes - balance between diabatic and adiabatic mechanisms

  摘要：

  The mechanism for triplet-sensitized cis-trans photoisomerization of three bisstyrylarenes, 1-3, has been studied by quantum yield measurements and laser flash photolysis. The triplet-state lifetimes for all three molecules are long enough to give an isomerization pattern essentially determined by the thermodynamics of the triplet excited-state surface, that is, equilibration processes are much faster than decay processes. Decay from the triplet excited-state surface occurs to various degrees from two equilibrated states, the planar 3E,E* and another with one double bond twisted, 3E,p*. Extension of pi-conjugation gives more 2-fold cis-trans isomerization, from the Z,Z isomer to the E,E isomer, due to aa more facile adiabatic than diabatic pathway for the isomerization reaction. For one of the molecules, 9,10-bisstyrylanthracene, 3, the Z,Z isomer undergoes exclusively 2-fold isomerization to yield the E,E isomer. 1,4-Bis(3,5-di-tert-butylstyryl)naphthalene, 2, shows mainly 2-fold isomerization from the Z,Z isomer, but there is also a diabatic contribution to this isomerization giving a photostationary state, ZE:EE, 18:82. For 4,4'-bis(3,5-di-tert-butylstyryl)biphenyl, 1, the isomerization is still partly adiabatic. There is no decay from the 3Z,p* but all decay occurs from 3E,p*, giving a photostationary state ZE:EE, ca. 50:50. The photostationary states for the bisstyrylnaphthalene and the bisstyrylbiphenyl can be affected by the addition of aa triplet quencher, azulene or perylene, to give almost pure E,E.

  DOI：

  10.1021/j100196a034

文献信息

• Rotaxane or Pseudorotaxane? Effects of Small Structural Variations on the Deslipping Kinetics of Rotaxanes with Stopper Groups of Intermediate Size
  作者：Ansgar Affeld、Gosia M. Hübner、Christian Seel、Christoph A. Schalley

  DOI：10.1002/1099-0690(200108)2001:15<2877::aid-ejoc2877>3.0.co;2-r

  日期：2001.8

  Secondly, stopper flexibility has an important influence on the deslipping rate. Thirdly, exchange of a carbonamide for a sulfonamide in the wheel significantly reduces the entropic costs of the deslipping, resulting in a pronounced deslipping rate enhancement. Fourthly, intramolecular hydrogen bonding within the wheel decelerates deslipping by a factor of more than 104.

  三个系列的轮烷已通过滑动合成（轴和轮混合熔化）、通过识别大环轮内部的酰胺基团或通过阴离子模板法（其中塞子酚盐与轮以氢键键合）的方式合成。然后通过与半轴的反应连接。大多数这些轮烷使用的 3,5-二叔丁基苯基塞子足够大，可以隔离它们，但在适当的条件下仍允许车轮从轴上滑落。所有轮烷的脱滑活化参数均来自 1 H NMR 动力学测量值，并已根据 Arrhenius 方程和 Eyring 理论进行评估。小的结构变化会对激活参数产生惊人的影响。首先，在一些例子中，轴长影响防滑屏障，但止动器和车轮的尺寸互补性保持不变。其次，塞子的柔韧性对脱滑率有重要影响。第三，在车轮中用碳酰胺交换磺酰胺显着降低了脱滑的熵成本，从而显着提高了脱滑率。第四，车轮内的分子内氢键使滑移减速超过 104 倍。
• Schenk, Rainer; Gregorius, Heike; Meerholz, Klaus, Journal of the American Chemical Society, 1991, vol. 113, # 7, p. 2634 - 2647
  作者：Schenk, Rainer、Gregorius, Heike、Meerholz, Klaus、Heinze, Jürgen、Mülen, Klaus

  DOI：——

  日期：——
• Size Complementarity of Macrocyclic Cavities and Stoppers in Amide-Rotaxanes
  作者：Christiane Heim、Ansgar Affeld、Martin Nieger、Fritz Vögtle

  DOI：10.1002/(sici)1522-2675(19990505)82:5<746::aid-hlca746>3.0.co;2-c

  日期：1999.5.5

  New [2]rotaxanes were prepared by the threading and the slipping procedure, the latter having the advantage of not needing templating interactions. As a consequence, the first [2]rotaxane consisting of a tetraamide macrocycle and a pure hydrocarbon thread was synthesized (see 12a in Scheme 2). Sterically matching wheels and axles being the basic requirement of a successful slipping approach to rotaxanes, mono- and bishomologous wheels 5b, c with larger diameters than the parent 5a were synthesized and mechanically connected to amide axles 10a-c which were stoppered with blocking groups of different spatial demand (Scheme 1). The deslipping kinetics of the resulting rotaxanes 8a-c and 9a,b were measured and compared; it emerges that even slight increases in the wheel size require larger stoppers to stabilize the mechanical bond. Moreover, when the deslipping rate of 8a (amide wheel and amide axle) was determined in either DMF or THF, a strong dependence on the solvent polarity, which is caused by a differing extent of intramolecular H-bonds between the wheel and the axle, was observed. As expected, no such dependence was detected for rotaxane 12a (amide wheel and hydrocarbon axle) whose components cannot interact via ii-bonds. The comparison of the sterically matching pairs of macrocycles and blocking groups, found by a systematic fitting based on the results of slipping and deslipping experiments, with other rotaxane types bearing similar stoppers allows conclusions concerning the relative cavity size of wheels of various structure.
• SCHENK, RAINER;GREGORIUS, HEIKE;MEERHOLZ, KLAUS;HEINZE, JURGEN;MULLEN, KL+, J. AMER. CHEM. SOC., 113,(1991) N, C. 2634-2647
  作者：SCHENK, RAINER、GREGORIUS, HEIKE、MEERHOLZ, KLAUS、HEINZE, JURGEN、MULLEN, KL+

  DOI：——

  日期：——
• Schenk,Rainer; Hucker, Joachim; Hopf, Henning, Angewandte Chemie, 1989, vol. 101, # 7, p. 942 - 944
  作者：Schenk,Rainer、Hucker, Joachim、Hopf, Henning、Raeder, Hans-Joachim、Muellen, Klaus

  DOI：——

  日期：——