4''-hydroxy-1,1':4',1''-terphenyl-4-carbonitrile | 160347-76-2

• 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-1,1':4',1''-terphenyl-4-carbonitrile
• 英文别名: 4-hydroxy-4''-cyano-p-terphenyl；4-hydroxy-4'-cyanoterphenyl；4-[4-(4-Hydroxyphenyl)phenyl]benzonitrile；4-[4-(4-hydroxyphenyl)phenyl]benzonitrile
• CAS: 160347-76-2
• 化学式: C₁₉H₁₃NO
• 分子量: 271.318
• InChiKey: SNBXPVNMXUKTBT-UHFFFAOYSA-N

物化性质

• 沸点：
  502.1±38.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-辛炔酸 、 4''-hydroxy-1,1':4',1''-terphenyl-4-carbonitrile 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以81%的产率得到4'-cyano-4-terphenylyl-2-octynate
  参考文献：
  名称：

  Synthesis and thermal analysis of disubstituted propiolates bearing terphenylene mesogen

  摘要：

  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。

  DOI：

  10.1007/s10973-009-0199-9
• 作为产物：
  描述：

  4-羟基-4'-溴联苯 、 4-氰基苯硼酸 在 5%-palladium/activated carbon 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以88%的产率得到4''-hydroxy-1,1':4',1''-terphenyl-4-carbonitrile
  参考文献：
  名称：

  木炭催化的铃木-宫浦反应中钯催化合成羟基取代的对三联苯和一些较大的低聚亚苯基

  摘要：

  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。

  DOI：

  10.1002/adsc.201600487

文献信息

• Effects of substitution and terminal groups for liquid-crystallinity enhanced luminescence of disubstituted polyacetylenes carrying chromophoric terphenyl pendants
  作者：Dan Zhou、YiWang Chen、Lie Chen、Fan Li、HuaRong Nie、Kai Yao

  DOI：10.1007/s11426-010-3166-1

  日期：2010.6

  Liquid-crystalline and light-emitting poly(2-alkyne)s containing terphenyl cores with hexamethyleneoxy spacers, and cyano or n-propoxy tails −“[CH3C=C(CH2)6O-terphenyl-R]” n −, where R=CN, CH3PA6CN, R=OCH2CH2CH3, CH3PA6OPr, were synthesized. The effects of the substitution and terminal groups on the properties, especially the mesomorphic and optical properties of the polymers, were investigated. The disubstituted acetylene monomers (CH3A6CN, CH3A6OPr) were prepared through multistep reaction routes and were polymerized by WCl6-Ph4Sn in good yields (up to 82%). All the monomers and CH3PA6CN exhibited the enantiotropic SmA phase with a monolayer arrangement at elevated temperatures, whereas CH3PA6OPr formed a bilayer SmAd packing arrangement. Upon excitation at 330 nm, strong UV and blue emission peaks at 362 and 411 nm were observed in CH3PA6OPr and CH3PA6CN, respectively. The luminescent properties of CH3PA6CN and CH3PA6OPr have been improved by introducing the methyl substituted group, and the quantum yield of the polymer with cyano tail CH3PA6CN (Φ = 74%) was found to be higher than that of CH3PA6OPr (Φ = 60%). Compared to polyacetylene parents, both CH3PA6OPr and CH3PA6CN showed a narrower energy gap. This demonstrated that the electrical conductivities of polyacetylenes could be enhanced by attaching appropriate pendants to the conjugated polyene backbones.

  含六甲ylene氧间隔基和氰基或n-丙氧基尾的特苯核心的液晶和发光聚（2-炔）（"-[CH3C=C（CH2）6O-特苯基-R]n-"，其中 R=CN，CH3PA6CN，R=OCH2CH2CH3，CH3PA6OPr）被合成。研究了取代基和末端基团对聚合物特性，特别是液晶和光学特性的影响。通过多步反应路线制备了二取代乙炔单体（CH3A6CN，CH3A6OPr），并通过 WCl6-Ph4Sn 聚合得到了良好的产率（高达 82%）。所有单体和 CH3PA6CN 在升高温度下表现出单层排列的反向 SmA 相，而 CH3PA6OPr 形成了双层 SmAd 堆积排列。在 330 nm 激发下，CH3PA6OPr 和 CH3PA6CN 分别观察到 362 和 411 nm 的强 UV 和蓝光发射峰。通过引入甲基取代基团，CH3PA6CN 和 CH3PA6OPr 的发光特性得到了改善，氰基尾聚合物 CH3PA6CN 的量子产率（Φ = 74%）被发现高于 CH3PA6OPr（Φ = 60%）。与聚乙炔母体相比，CH3PA6OPr 和 CH3PA6CN 都显示出更窄的能隙。这表明通过将适当的支链附着到共轭多烯骨架上，可以提高聚乙炔的电导率。
• DIBENZOTHIOPHENE OXIDE COMPOUND, AND PROCESS FOR PRODUCING THE SAME
  申请人：Sekine Chizu

  公开号：US20080139824A1

  公开（公告）日：2008-06-12

  There are disclosed novel compounds, liquid crystal compositions, polymers, optically anisotropic products, and optical or liquid or liquid crystal elements that have large refractive index anisotropy, mix easily with other liquid crystals, have advantageous stability against light, and exhibit absorption at practically short wavelength in the ultraviolet region. The compounds are represented by the formula (1) and have a phenylacetylene structure, wherein difference ΔE in energy of HOMO of parts (1-1), (1-2) and (1-3) calculated by the method of molecular orbitals is not less than 0.3 electronvolt, and the polarizability anisotropy Δα of a molecule represented by the formula (1) calculated in the same way is not lower than 500 A.U.: (A 1 to A 4 : H, F, alkyl or alkoxy group of C1 to C10 optionally substituted with F; P 1 , P 2 ; structure fulfilling the conditions of HOMO energy and polarizability).

  本发明公开了新型化合物、液晶组合物、聚合物、光学各向异性产品和具有大折射率各向异性、易于与其他液晶混合、对光稳定性有优势、在紫外区域实际短波长处表现出吸收的光学或液晶元素。这些化合物由公式（1）表示，具有苯乙炔结构，其中通过分子轨道法计算的部分（1-1）、（1-2）和（1-3）的HOMO能级差ΔE不小于0.3电子伏，公式（1）所代表的分子的极化率各向异性Δα在同样的方法下计算不低于500 A.U.：（A1至A4：C1至C10的氢、氟、烷基或烷氧基，可选地取代为氟；P1、P2：符合HOMO能量和极化率条件的结构）。
• COMPOUND HAVING PHENYLACETYLENE STRUCTURE, LIQUID CRYSTAL COMPOSITION, POLYMER, OPTICALLY ANISOTROPIC PRODUCT, OPTICAL OR LIQUID CRYSTAL ELEMENT, DIBENZOTHIOPHENE COMPOUND, INTERMEDIATE, AND PROCESS FOR PRODUCING THE SAME
  申请人：Sekine Chizu

  公开号：US20070057229A1

  公开（公告）日：2007-03-15

  There are disclosed novel compounds, liquid crystal compositions, polymers, optically anisotropic prodrugs, and optical or liquid crystal elements that have large refractive index anisotropy, mix easily with other liquid crystals, have advantageous stability against light, and exhibit absorption at practically short wavelength in the ultraviolet region. The compounds are represented by the formula (1) and have a phenylacetylene structure, wherein difference ΔE in energy of HOMO of parts (1-1), (1-2) and (1-3) calculated by the method of molecular orbitals is not less than 0.3 electronvolt, and the polarizability anisotropy Δα of a molecule represented by the formula (1) calculated in the same way is not lower than 500 A.U.: (A 1 to A 4 : H, F, alkyl or alkoxy group of C1 to C10 optionally substituted with F; P 1 , P 2 : structure fulfilling the conditions of HOMO energy and polarizability).

  本发明涉及一种新型化合物、液晶组合物、聚合物、光学各向异性前药和具有大折射率各向异性、容易与其他液晶混合、对光稳定性有优势、并在紫外区域表现出实际短波长吸收的光学或液晶元素。化合物由公式（1）表示，具有苯乙炔结构，其中分子轨道法计算的部分（1-1）、（1-2）和（1-3）的HOMO能量差ΔE不小于0.3电子伏特，以及以相同方式计算的由公式（1）表示的分子的极化率各向异性Δα不低于500 A.U.：（A1至A4：C1至C10的H、F、烷基或烷氧基，可选地取代F；P1、P2：满足HOMO能量和极化率条件的结构）。
• 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.
• 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。