3,4-bis(tetradecyloxy)benzaldehyde | 131525-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4-bis(tetradecyloxy)benzaldehyde
• 英文别名: 3,4-Di(tetradecoxy)benzaldehyde
• CAS: 131525-54-7
• 化学式: C₃₅H₆₂O₃
• 分子量: 530.875
• InChiKey: LDRVIFLAXCLQTD-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C(Solv: ethanol (64-17-5))
• 沸点：
  612.6±35.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  38
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis(tetradecyloxy)benzaldehyde 在 吡啶 、 硫酸 、 二正丙胺 作用下， 以 苯 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  Photopolymerization of Carbohydrate-Based Discotic Mesogens. Syntheses and Phase Properties of 1,2,3,4,6-Penta-O-(trans-3,4-dialkoxycinnamoyl)-(d)- glucopyranoses and Their Oligomers

  摘要：

  The neat phase properties of the alpha and beta anomers of 1,2,3,4,6-penta-O-(trans-3,4-dialkoxycinnamoyl) (D)-glucopyranose (n alpha GP and n beta GP; n, the number of carbon atoms in the alkyl chains, is 6-8, 10, and 14) have been investigated by optical microscopy, differential scanning calorimetry, and X-ray powder diffraction. Each of the GP forms an enantiotropic and thermotropic discotic columnar liquid-crystalline phase. Irradiation of the 14GP in dilute solutions leads to two intramolecular [2 + 2] cycloaddition reactions between cinnamoyl double bonds. In the solid I (obtained by recrystallization from solvent and in which 14GP molecules are paired in each columnar stack) and ''isotropic'' melt phases, only short (<10 monomer unit), probably branched oligomers form upon irradiation due to the continued preference for intramolecular cycloadditions and the ability of each monomer to interact with more than two neighbors. Irradiation of the solid II phase (obtained by cooling the liquid-crystalline phase) provides unbranched oligomers with <20 monomer units. However; more than 30 14 alpha GP monomer units have been linked in unbranched chains upon irradiation of its liquid-crystalline phase. This is the greatest degree of columnar polymerization reported to date from a discotic mesophase. Qualitatively similar results are obtained upon irradiation of other GP in their various phases. Oligomerization of GP liquid-crystalline and solid I phases is intracolumnar, and the columnar packing arrangement of-the monomers is retained to ca. 100 degrees C above their clearing temperatures; each GP produces nanoscale cylinders of one diameter but varying lengths. The oligomers unwind and do not retake their original form when they are dissolved and reprecipitated or heated to above their clearing temperatures and cooled. The nature of the oligomerization processes is discussed, especially with regard to inter-/intramolecular and inter-/intracolumnar competitions for [2 + 2] cycloaddition reactions and the possibility of an anomeric effect on oligomer length.

  DOI：

  10.1021/ja961665x
• 作为产物：
  描述：

  溴代十四烷 、 3,4-二羟基苯甲醛 生成 3,4-bis(tetradecyloxy)benzaldehyde
  参考文献：
  名称：

  基于氰基吡啶酮的新型发光液晶材料：合成与表征。

  摘要：

  新系列的4-（3,4-双（烷氧基）苯基）-6-（4-（（1-（4-氰基或4-硝基苄基）-1H-1,2,3-三唑-带有末端二烷氧基链长（即辛氧基，癸氧基，十二烷氧基，十四烷氧基和十六烷基烷氧基）以及末端极性基团的4-基）甲氧基）苯基）-2-氧-1,2-二氢吡啶-3-腈或-NO2已被成功设计并合成为发光液晶元。已经通过差示扫描量热法和偏振光学显微镜研究了它们的热致行为。通过温度依赖性X射线衍射法探索了其中的超分子组织，并使用紫外可见和荧光光谱法研究了它们的光物理性质。介晶研究表明，氢键的存在以及分子之间的二聚化，主要负责在新分子中形成环境六方柱状相（Colh）。他们的光物理研究表明，与氯仿中的奎宁硫酸盐（Phif = 0.54）相比，该化合物在约370 nm处有很强的吸收带，在约466 nm处有蓝色的发射带，量子产率约为0.62。同样，化合物在吸收带中显示出轻微的红移，并伴随着溶剂极性的增加。

  DOI：

  10.1039/c4pp00031e

文献信息

• Tuning the thermotropic properties of liquid crystalline p-substituted aroylhydrazones
  作者：Hemant Kumar Singh、Sachin Kumar Singh、Rajib Nandi、Madan Kumar Singh、Vijay Kumar、Ranjan K. Singh、D. S. Shankar Rao、S. Krishna Prasad、Bachcha Singh

  DOI：10.1039/c5ra06620d

  日期：——

  Lamellar smectic A to columnar mesophase crossover is observed in p-substituted aroylhydrazones by variation of the alkoxy chain density at peripherals.

  通过改变周边烷氧链密度，在p-取代芳酰肼中观察到片层烟酸A到柱状介晶相的交叉。
• Discotic metallomesogens: mesophase crossover of columnar rectangular to hexagonal arrangements in bis(hydrazinato)nickel(II) complexes
  作者：Chung K. Lai、Chun-hsien Tsai、Yung-shyen Pang

  DOI：10.1039/a800657a

  日期：——

  Three series ofN-(3,4-dialkoxybenzylidene)-N′-(3′,4′,5′-trialkoxybenzoyl)hydrazine and their nickel(ii) complexes, bis[N-(3,4-dialkoxybenzylidene)-N′-(3′,4′,5′-trialkoxybenzoyl)hydrazinato]nickel(ii), were prepared and characterized. The mesomorphic properties of these disc-like compounds were also studied in terms of liquid crystallinity. The orange nickel(ii) complexes with ten soft alkoxy side chains exhibited columnar disordered mesophases, which were characterized based on DSC analysis and optical polarized microscopy. Nickel complexes with shorter side chains (n=5–8) displayed a monotropic columnar rectangular disordered (Colrd) phase; however, complexes with longer side chains showed monotropic (n=10) and enantiotropic (n=12, 14) columnar hexagonal disordered (Colhd) phases. Similar nickel complexes (n=14) with eight side chains exhibited a columnar hexagonal phase, whereas complexes (n=14) with six side chains formed crystalline phases. The structures of these columnar disordered phases were confirmed by X-ray powder diffraction. XRD data indicated that mesophase crossover from columnar rectangular (Colr) to hexagonal arrangements (Colh) was observed with increasing side chain lengths.

  合成了三种系列的N-(3,4-二烷氧基亚苄基)-N′-(3′,4′,5′-三烷氧基苯甲酰)酰肼及其镍(II)配合物,[N-(3,4-二烷氧基亚苄基)-N′-(3′,4′,5′-三烷氧基苯甲酰)酰氨基]合镍(II),并对化合物进行了表征。我们还研究了这些类圆盘状化合物的液晶特性。具有十个柔软烷氧基侧链的橙色镍(II)配合物表现出柱状无序液晶相,这一特性通过DSC分析和光学偏振显微镜得到了表征。含有较短侧链(n=5–8)的镍配合物呈现出单变型柱状矩形无序(Colrd)相;然而,具有更长侧链的配合物呈现出单变型(n=10)和同变型(n=12, 14)柱状六方无序(Colhd)相。类似镍配合物(n=14)具有8个侧链时出现柱状六方相,而6个侧链时则形成晶态相。这些柱状无序相的结构通过X射线粉末衍射得到了确认。XRD数据显示,随着侧链长度的增加,液晶相从柱状矩形(Colr)转变为六方排列(Colh)。
• 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, Characterization, and Mesomorphic Properties of New Pyridine Derivatives
  作者：Ahipa T. N.

  DOI：10.1002/open.201500158

  日期：2015.12

  Luminescent liquid crystals have received significant research interest due to their wide range of applications. Here, new pyridine derivatives were designed as liquid crystalline materials. They were successfully synthesized via appropriate synthetic routes, their structures confirmed by various spectral techniques, and finally characterized for their mesogenic, optical and optoelectronic properties

  发光液晶由于其广泛的应用而受到了广泛的研究兴趣。在这里，新的吡啶衍生物被设计为液晶材料。它们是通过适当的合成路线成功合成的，其结构已通过各种光谱技术证实，并最终通过介晶，光学和光电特性进行了表征。
• Discotic liquid crystals of transition metal complexes 42: the detailed phase structures and phase transition mechanisms of two Cub mesophases shown by discotic liquid crystals based on phthalocyanine metal complexes
  作者：Hidetomo Mukai、Miho Yokokawa、Masahiro Ichihara、Kazuaki Hatsusaka、Kazuchika Ohta

  DOI：10.1142/s1088424610001908

  日期：2010.2

  [Formula: see text] and [Formula: see text], respectively. However, their detailed phase structures were not revealed in the previous works. In this work, we have synthesized a series of novel sandwich-type phthalocyanine-based terbium complexes, bis[2,3,9,10,16,17,23,24-octakis(3,4-dialkoxyphenoxy)phthalocyaninato]terbium(III) ([( C n O )2 PhO ]8 Pc }2 Tb , n = 8–16) (2). Their mesomorphic properties have

  我们在之前的工作中发现夹心型酞菁基稀土金属配合物双[2,3,9,10,16,17,23,24-octakis(3,4-dialkoxyphenoxy)phthalocyaninato]lanthanoid(III ） （[（ Cn○）2磷]8个人电脑 }2M, M = Eu 和 Lu, n = 8-16) (1 和 3), 表现出两个热致立方中间相 Cub1和幼崽2，以及柱状中间相。盘状液晶化合物很少显示立方中间相。我们揭示了它们对低温 Cub 的对称性1中间相和更高温度的 Cub2中间相分别为[公式：见正文]和[公式：见正文]。然而，它们的详细相结构在以前的作品中没有透露。在这项工作中，我们合成了一系列新型夹心型酞菁基铽配合物，双[2,3,9,10,16,17,23,24-八(3,4-二烷氧基苯氧基)酞菁]铽(三）（[（Cn○）2磷]8个人电脑 }2Tb , n = 8-16) (2)。已经使用偏光显微镜、DSC