4-hydroxy-4'-methoxy-p-terphenyl | 94459-00-4

• 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-hydroxy-4'-methoxy-p-terphenyl
• 英文别名: 4''-methoxy-1,1':4',1''-terphenyl-4-ol；4-[4-(4-Methoxyphenyl)phenyl]phenol
• CAS: 94459-00-4
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: AWGKLAKGVMZIFA-UHFFFAOYSA-N

物化性质

• 沸点：
  471.3±33.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4'-methoxy-p-terphenyl 在 吡啶盐酸盐 、 水 作用下， 反应 12.0h， 以100%的产率得到[1,1’:4’,1’’-三联苯]-4,4’’-二醇
  参考文献：
  名称：

  Synthesis of oligophenylenes containing hydroxyl group and their solvatochromic behavior

  摘要：

  Oligo(p-phenylene)s containing hydroxyl group(s), namely, OPP(n)-OH (n=3, 4, and 5; it denotes the number of benzene rings), HO-OPP(3)-OH, and 1,3,5-tri(4-biphenyl)phenol TBP-OH were synthesized in high yields by the Suzuki coupling reaction. Absorption maxima (lambda(max)s) of OPP(n)-OHs shifted progressively toward long wavelengths due to the expansion of the pi-conjugation system with an increase in the number of benzene rings. Deprotonation of the OH group of OPP(n)-OHs by treatment with NaH caused a bathochromic shift of lambda(max). The bathochromic shift of the deprotonated species increased with the donor numbers (DNs) of the solvents. The emission peak positions of OPP(n)-OH and OPP(n)-ONa depended on the DN of the solvents; that is, the emission color could be tuned by changing the solvent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.073
• 作为产物：
  描述：

  环己-2,5-二烯-1-酮 在 三溴化硼 、 对甲苯磺酸 、 magnesium 作用下， 以 苯 为溶剂， 反应 9.0h， 生成 4-hydroxy-4'-methoxy-p-terphenyl
  参考文献：
  名称：

  Synthesis and properties of high-temperature mesomorphic polysiloxane (MEPSIL) solvents: biphenyl- and terphenyl-based nematic systems

  摘要：

  DOI：

  10.1021/ac00280a019

文献信息

• Synthesis and thermal analysis of disubstituted propiolates bearing terphenylene mesogen
  作者：Lie Chen、Yiwang Chen、Weihua Zhou、Xiaohui He、Yanlin Song、Zhijie Zhang

  DOI：10.1007/s10973-009-0199-9

  日期：2010.2

  Novel disubstituted propiolates bearing chromophoric terphenylene mesogenic groups, namely, 4′-cyano-4-terphenylyl-2-octynate M(CN) and 4′-methoxyl-4-terphenylyl-2-octynate M(OCH3) are synthesized, where the terphenyl groups are connected to the C≡C through ester linkage directly. Using transition-metal catalysts such as the classical MoCl5- and WCl6-based metathesis catalysts, the polymerization of the M(CN) and M(OCH3) are carried out in a series of different solution, however, did not obtain any products. It suggests that the WCl6- and MoCl5-based catalysts are poisoned by the polar groups, on the other hand, the bulk terphenyl groups and the long alkyl chain around the C≡C bond might inhibit the reaction. M(CN) displays monotropic nematicity, whereas M(OCH3) exhibits enantiotropic nematicity and smecticity (SmAd) with a bilayer arrangement when cooled and heated. Ultraviolet spectroscopy and photoluminescence measurements also show that the terphenyl groups endow disubstituted propiolates with strong UV light absorption and high photoluminescence.

  合成了具有色品特苯介质基团的新型二取代丙炔酸酯，分别为4′-氰基-4-特苯基-2-辛酸酯M(CN)和4′-甲氧基-4-特苯基-2-辛酸酯M(OCH3)，其中特苯基团通过酯键直接与C≡C连接。通过使用过渡金属催化剂，如经典的基于MoCl5和WCl6的复分解催化剂，在一系列不同的溶液中进行M(CN)和M(OCH3)的聚合实验，然而未能获得任何产物。这表明WCl6和MoCl5基催化剂被极性基团毒化，另一方面，体积较大的特苯基团和C≡C键周围的长烷基链可能抑制了反应。M(CN)显示出单向性向列相，而M(OCH3)在冷却和加热时则表现出对称性向列相和层状相（SmAd），呈双层排列。紫外光谱和光致发光测量结果也表明，特苯基团赋予了二取代丙炔酸酯强烈的紫外光吸收和高光致发光性能。
• Synthesis of Hydroxy-Substituted<i>p</i>-Terphenyls and some Larger Oligophenylenes<i>via</i>Palladium on Charcoal Catalyzed Suzuki-Miyaura Reaction
  作者：Josef Jansa、Tomáš Řezníček、Roman Jambor、Filip Bureš、Antonín Lyčka

  DOI：10.1002/adsc.201600487

  日期：2017.1.19

  A ligand‐free heterogeneous palladium on charcoal (Pd/C)‐catalyzed Suzuki‐Miyaura cross‐coupling has been performed. The series of substituted p‐terphenyls were prepared in very good yields without exclusion of air and with low catalyst loadings. Moreover, the developed environmentally benign and scalable protocol enables to use electron poor and sterically hindered boronic acids.

  在木炭（Pd / C）催化的Suzuki-Miyaura交叉偶联反应中进行了无配体的非均相钯。一系列取代的对叔苯基制备得非常好，没有排除空气，催化剂用量也很低。而且，开发的环境友好和可扩展的协议使得能够使用电子贫乏和空间受阻的硼酸。
• Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant
  作者：Lie Chen、Yiwang Chen、Weihua Zhou、Fan Li、Xiaohui He、Ben Zhong Tang

  DOI：10.1080/15421400903568047

  日期：2010.3.22

  A series of polythiophenes containing terphenyl mesogenic side chain at the third position through ester bonding was synthesized by dehalogenative polycondensation. The thiophene monomers 2,5-bromo-3-[(4-(4'-cyano)terphenyloxy)carbonyl]-methyl]}-thiophene [M(CN)] and 2,5-bromo-3-[(4-(4'-methoxy)terphenyloxy)-carbonyl]methyl}-thiophene [M(OCH3)] were prepared via Suzuki reation and esterification reactions, in sequence. The structures and properties of the monomers and polymers were characterized and evaluated with nuclear magnetic resonance, infrared spectroscopy, thermogravimetry, differential scanning calorimetry, polarized optical microscopy, ultraviolet spectroscopy, and photoluminescence. All of the polymers were stable, losing little of their weights when heated to epsilon 300 degrees C. The polymers showed good solubility and could be dissolved in common solvents such as CHCl3, THF, DMF, etc. The monomers exhibited enantiotropic SmAd phases with a bilayer arrangement in the heating and cooling processes. Due to short spacer methylene ester between the bulk terphenyl mesogenic side chain and rigid polythiophene main chain, the polymers could not exhibit liquid crystallinty at elevated temperature. The existence of the chromophoric terphenyl core endows the polymers with high photoluminescence. When their CH2Cl2 solutions were photoexcited, the polymers emitted a strong UV light about 400nm.
• OLIGOMERIC ORGANIC LIGHT EMITTING DIODE(OLED)MATERIALS CONTAINING MULTIPLE CROSSLINKING FUNCTIONS
  申请人：Lomox Limited

  公开号：EP2847809B1

  公开（公告）日：2017-12-20
• [EN] OLIGOMERIC ORGANIC LIGHT EMITTING DIODE(OLED)MATERIALS CONTAINING MULTIPLE CROSSLINKING FUNCTIONS<br/>[FR] MATÉRIAUX OLIGOMÈRES DE DIODE ÉLECTROLUMINESCENTE ORGANIQUE (OLED) CONTENANT DE MULTIPLES FONCTIONS DE RÉTICULATION
  申请人：LOMOX LTD

  公开号：WO2013167857A1

  公开（公告）日：2013-11-14

  OLED materials having the formula: T-— A(— S— B(— P— B)m— S— A)n— T where A are independently selected rod-shaped, rigid molecular core units, S are independently selected flexible spacer units, B are polymerisable crosslinking groups independently selected, P are spacer groups independently selected, T are independently selected end groups, m are independently selected from values of from 1 to 4, n is equal to I to 3.