p-(Tetradecyloxy)pentylacetylene | 160094-57-5

• 英文名称: p-(Tetradecyloxy)pentylacetylene
• 英文别名: 4-tetradecyloxyphenylacetylene；1-tetradecyloxy-4-ethynylbenzene；4-ethynyl-1-(tetradecyloxy)benzene；1-Ethynyl-4-tetradecoxybenzene
• CAS: 160094-57-5
• 化学式: C₂₂H₃₄O
• 分子量: 314.511
• InChiKey: YFYHIPYUDZHPHW-UHFFFAOYSA-N

物化性质

• 沸点：
  413.2±28.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-(Tetradecyloxy)pentylacetylene 在 正丁基锂 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-<4-(Tetradecyloxy)phenyl>-3-(4-nitrophenyl)-1,3-butadiyne
  参考文献：
  名称：

  Preparation and Coupling Reactions of Alkynyl(phenyl)iodonium Salts Bearing Long Alkoxy Chains. Formation of Liquid-Crystalline Diacetylenes

  摘要：

  Alkynyl(phenyl)iodonium tosylates with long alkoxy chains, such as (octyloxy)-, (decyloxy)-, (dodecyloxy)-, and (tetradecyloxy)phenyl, were prepared by reaction of the corresponding alkynes with hydroxy(tosyloxy)iodobenzene. The alkynyliodonium tosylates were allowed to react with alkynylcopper reagents (p-RC(6)H(4)C=C)(2)Cu(CN)Li-2, where R = MeO, Me, H, Br, CN, and NO2. The coupling reaction proceeded under mild conditions to provide unsymmetrical and symmetrical diacetylenes. The selectivity of the formation of these diacetylenes was dependent on the substituent on the alkynylcopper reagents. The diacetylenes prepared in this study displayed liquid-crystalline properties.

  DOI：

  10.1021/jo00105a022
• 作为产物：
  描述：

  1-(4-tetradecyloxyphenyl)-ethanone 在 sodium hydroxide 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 p-(Tetradecyloxy)pentylacetylene
  参考文献：
  名称：

  Preparation and Coupling Reactions of Alkynyl(phenyl)iodonium Salts Bearing Long Alkoxy Chains. Formation of Liquid-Crystalline Diacetylenes

  摘要：

  Alkynyl(phenyl)iodonium tosylates with long alkoxy chains, such as (octyloxy)-, (decyloxy)-, (dodecyloxy)-, and (tetradecyloxy)phenyl, were prepared by reaction of the corresponding alkynes with hydroxy(tosyloxy)iodobenzene. The alkynyliodonium tosylates were allowed to react with alkynylcopper reagents (p-RC(6)H(4)C=C)(2)Cu(CN)Li-2, where R = MeO, Me, H, Br, CN, and NO2. The coupling reaction proceeded under mild conditions to provide unsymmetrical and symmetrical diacetylenes. The selectivity of the formation of these diacetylenes was dependent on the substituent on the alkynylcopper reagents. The diacetylenes prepared in this study displayed liquid-crystalline properties.

  DOI：

  10.1021/jo00105a022

文献信息

• Synthesis, mesomorphism, photophysics and device performance of liquid-crystalline pincer complexes of gold(<scp>iii</scp>)
  作者：Rachel R. Parker、Denghui Liu、Xiankang Yu、Adrian C. Whitwood、Weiguo Zhu、J. A. Gareth Williams、Yafei Wang、Jason M. Lynam、Duncan W. Bruce

  DOI：10.1039/d0tc04839a

  日期：——

  the condensed phase. Solution NMR studies show a preferred orientation for self-association, consistent with structural parameters in the liquid crystal phase obtained by X-ray methods. While the pattern of substitution of the phenylacetylide has no discernible effect on the photophysics, when two alkoxy chains are attached to the pincer ligands, photoluminescence quantum yields (PLQY) of around 3% are

  发光金（III）也带有苯基乙酰胺配体的2,6-二苯基吡啶的螯合剂的络合物在钳子和苯乙炔化物上均已被修饰以赋予液晶性质，大多数络合物在缩合相中显示出柱状六方相。溶液NMR研究表明自缔合的优选取向与通过X射线方法获得的液晶相中的结构参数一致。尽管苯乙炔化物的取代模式对光物理没有明显影响，但是当两个烷氧基链连接到钳形配体时，发现的光致发光量子产率（PLQY）约为3％，而当四个烷氧基链连接时，PLQY会增加明显达到36％。来自计算化学的见解表明，烷氧基供体基团的引入提高了基于钳子的HOMO-1轨道的能量，同时伴随着LUMO←HOMO-1过渡能的降低，这与实验观察到的红移一致。使用溶液处理方法将金络合物制成OLED器件，然后将其掺入5％的发光层中，从而使外部量子效率高达7.14％，该值与文献中相关络合物的性能相当。
• Synthesis, mesomorphic properties and nonlinear optical studies of alkyl and alkoxy phenylacetylene containing phenazine fused extended triphenylene discotic liquid crystalline dyes
  作者：Ashwathanarayana Gowda、Litwin Jacob、Alakananda Patra、Agnes George、Reji Philip、Sandeep Kumar

  DOI：10.1016/j.dyepig.2018.07.052

  日期：2019.1

  properties. They show a broad range of hexagonal columnar phase and retain their mesophase up to room temperature upon cooling from the isotropic liquid. Thermotropic liquid crystalline properties of all the compounds were studied by polarised optical microscopy (POM), differential scanning calorimetry (DSC). The self-assembly of mesophase structure was investigated by X-ray diffraction (XRD) studies. Thermogravimetric

  在本文中，我们报道了通过三亚苯基1,2-二醌与1,2-二氨基-4,5-二溴苯的缩合反应获得的含吩嗪稠合的亚苯基盘状液晶（DLC）的烷基和烷氧基苯基乙炔。 Sonogashira CC与4-烷基-苯基乙炔或4-烷氧基-苯基乙炔的偶联反应。合成了六种新型衍生物，并对其热和光学性质进行了评估。它们显示出广泛的六方柱状相，并在从各向同性液体冷却后将其中间相保持到室温。通过偏振光学显微镜（POM），差示扫描量热法（DSC）研究了所有化合物的热致液晶性质。通过X射线衍射（XRD）研究了中间相结构的自组装。所有介晶的热重分析表明，它在很宽的温度范围内都具有良好的热稳定性。在无水氯仿溶剂中使用UV-Vis吸收和光致发光发射光谱法测量了新合成化合物的光物理性质。这些介晶中的π扩展共轭表现出强吸收带，分别在270-487 nm左右下降，并在657-663 nm处具有相应的发射带。当在532 nm的纳秒激光脉冲
• Thermal and nonlinear optical studies of newly synthesized EDOT based bent-core and hockey-stick like liquid crystals
  作者：Ashwathanarayana Gowda、Litwin Jacob、Nithin Joy、Reji Philip、Pratibha R、Sandeep Kumar

  DOI：10.1039/c7nj04807f

  日期：——

  Novel EDOT based bent-core and hockey-stick shaped mesogens bearing terminal alkyl chains and alkoxy terminal chains, respectively, have been designed and synthesized via the Sonogashira coupling reaction. Molecular structures of these new compounds were determined using spectral and elemental analysis. The mesomorphic behaviour of all the novel compounds was primarily investigated by a combination

  新型EDOT基弯曲核和曲棍球状介晶分别带有末端烷基链和烷氧基末端链，已通过设计和合成，Sonogashira偶联反应。这些新化合物的分子结构使用光谱和元素分析确定。主要通过偏振光学显微镜（POM），差示扫描量热法（DSC）和X射线衍射研究（XRD）的组合研究了所有新化合物的介晶行为。所有化合物均以较低的同系物表现出对映向列相。但是，在较高的BC和曲棍球LC同源物中观察到了较低的近晶A相和高温向列相。进行了密度泛函理论研究以研究稳定构型。这些分子的弯曲角介于钙质LC和香蕉LC之间。在无水氯仿溶剂中研究了所有化合物的光物理性质，它们在370-395 nm左右具有吸收模式，在418-465 nm之间具有发射模式。我们还报道了当在532 nm的纳秒激光脉冲激发下测量时，这些新型化合物具有较大的有效两光子吸收率。所有介晶化合物都是非线性材料，这使其成为光学限制应用的合适候选物。
• Synthesis, thermal and photophysical studies of π–extended dibenzophenazine based discotic liquid crystals
  作者：Litwin Jacob、Ashwathanarayana Gowda、Sandeep Kumar、Victor Belyaev

  DOI：10.1016/j.molliq.2020.114419

  日期：2020.12

  differential scanning calorimetry (DSC). The self-assembly of mesophase structure of discotic mesogens were examined with the help of X-ray diffraction studies. All compounds exhibit stable hexagonal columnar mesophase over broad temperature range. The photophysical properties of these compounds were studied in anhydrous chloroform solvent at room temperature which exhibit absorption at 446–463 nm and corresponding

  已经设计并合成了新型的π-扩展的基于二苯并吩嗪的盘状介晶，与链烷硫醇和烷氧基苯乙炔以及烷氧基链相连。使用光谱和元素分析研究了所有化合物的分子结构。使用偏振光学显微镜（POM）和差示扫描量热法（DSC）对所有新型化合物的液晶性质进行了表征。借助X射线衍射研究检查了盘状介晶的中间相结构的自组装。所有化合物在宽温度范围内均表现出稳定的六角柱状中间相。在室温下于无水氯仿溶剂中研究了这些化合物的光物理性质，该溶剂在446-463 nm处有吸收，在578-600 nm处有相应的发射。
• Molecular 5,8-π-extended quinoxaline derivatives as chromophores for photoluminescence applications
  作者：Leonardo de O. Aguiar、Adalberto S.L. Junior、Ivan H. Bechtold、Sergio Fernando Curcio、Thiago Cazati、Tiago V. Alves、André Alexandre Vieira

  DOI：10.1016/j.molliq.2019.111763

  日期：2019.12

  The 5,8-π-extended quinoxaline derivatives are widely studied due to their well-known photophysical and electrochemical properties. In order to investigate the structure-property relationship, a novel series of fluorescent calamitic liquid crystals based on the quinoxaline heterocycle was successfully synthesized and characterized. The final molecules presented calamitic mesomorphism with nematic and

  由于其众所周知的光物理和电化学性质，对5,8-π-延伸的喹喔啉衍生物进行了广泛的研究。为了研究结构-性质之间的关系，成功地合成和表征了基于喹喔啉杂环的新型荧光cal族液晶。最终的分子呈现出向列相和近晶相的热分解。这些化合物在溶液和固态的紫外光激发下显示出强烈的绿色光致发光。在氯仿溶液中，荧光量子产率（Φ FL = 0.54–0.62）的基于喹喔啉的衍生物显着高于先前描述的类似苯并噻二唑的衍生物。最大发射峰在511和520 nm之间，具有纳秒级的单重激发态寿命。溶剂致变色研究表明，发射对溶剂极性的依赖性很大。用富勒烯C 60掺杂喹喔啉表明电荷转移过程，这取决于π共轭核。用DFT计算预测的能带隙与实验数据非常吻合。