(E)-N-phenyl-3,4,5-tris(dodecyloxy)benzaldimine | 117241-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-N-phenyl-3,4,5-tris(dodecyloxy)benzaldimine
• 英文别名: (E)-3,4,5-tris(dodecyloxy)-N-phenylbenzaldimin；(E)-N-phenyl-3,4,5-tridodecyloxybenzaldimine；(E)-N-Phenyl-3,4,5-tridodecyloxybenzaldimin
• CAS: 117241-34-6
• 化学式: C₄₉H₈₃NO₃
• 分子量: 734.203
• InChiKey: QVXMLHGZEYHAJL-PBFCBGGQSA-N

物化性质

• 熔点：
  37 °C(Solv: isopropanol (67-63-0))
• 沸点：
  759.5±60.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.34
• 重原子数：
  53.0
• 可旋转键数：
  38.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-N-phenyl-3,4,5-tris(dodecyloxy)benzaldimine 在 氢氧化钾 、 potassium tert-butylate 作用下， 以 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.25h， 生成 2,4-diamino-6-[(E,E)-4-[4-(3,4,5-tris-{dodecyloxy}styryl)-2,5-bis[(S)-2-methylbutoxy]styryl]phenyl]-s-triazine
  参考文献：
  名称：

  Transfer of π-Conjugated Columnar Stacks from Solution to Surfaces

  摘要：

  Three hydrogen-bonded oligo(p-phenylenevinylene)s, OPV3, OPV4, and OPV5, that differ in conjugation length have been synthesized and fully characterized. All three compounds contain chiral side chains, long aliphatic chains, and a ureido-s-triazine hydrogen bonding unit. H-1 NMR and photophysical measurements show that the OPV oligomers grow hierarchically in an apolar solvent; initially, dimers are formed by hydrogen bonds that subsequently develop into stacks by pi-pi interactions of the phenylenevinylene backbone with induced helicity via the chiral side chains. SANS measurements show that rigid cylindrical objects are formed. Stacks of OPV4 have a persistence length of 150 nm and a diameter of 6 nm. OPV3 shows rigid columnar domains of 60 nm with a diameter of 5 nm. Temperature and concentration variable measurements show that the stability of the stacks increases with the conjugation length as a result of more favorable pi-pi interactions. The transfer of the single cylinders from solution to a solid support as isolated objects is only possible when specific concentrations and specific solid supports are used as investigated by AFM. At higher concentrations, an intertwined network is formed, while, at low concentration, ill-defined globular objects are observed. Only in the case of inert substrates (graphite and silicium oxide) single fibers are visible. In the case of the repulsive surfaces (mica and glass), clustering of the stacks occurs, while, at attractive surfaces (gold), the stacks are destroyed.

  DOI：

  10.1021/ja0383118
• 作为产物：
  描述：

  3,4,5-三羟基苯甲醛 在 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 (E)-N-phenyl-3,4,5-tris(dodecyloxy)benzaldimine
  参考文献：
  名称：

  Meier, Herbert; Prass, Ellen; Zerban, Georg, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1988, vol. 43, # 7, p. 889 - 896

  摘要：

  DOI：

文献信息

• Liquid crystalline non-covalent supermolecules of a styrylstilbazole ligand
  作者：Jean-François Eckert、Urszula Maciejczuk、Daniel Guillon、Jean-François Nierengarten

  DOI：10.1039/b103563k

  日期：——

  Dimerization of a new styrylstilbazole ligand through non-covalent interactions leads to polycatenar calamitic supramolecular structures with liquid crystalline properties.

  一种新型苯乙烯基苯并咪唑配体通过非共价相互作用的二聚化，形成具有液晶特性的多链状灾难性超分子结构。
• Alkoxy substituted (E,E)-3,6-bis(styryl)pyridazine—a photosensitive mesogen for liquid crystals
  作者：Thorsten Lifka、Georg Zerban、Peter Seus、Annette Oehlhof、Herbert Meier

  DOI：10.1016/j.tet.2008.04.033

  日期：2008.6

  (E,E)-3,6-Bis(styryl)pyridazines (3a-t) bearing 2, 4 or 6 alkoxy chains were prepared by applying the Siegrist reaction of 3,6-dimethylpyridazine (13) and the corresponding azomethines 10a-t. The transversal dipole moment of these calamitic compounds effects an extremely high tendency for self-organization in thermotropic LC phases (N, S-A, S-B, S-C, S-E, S-1/F and Cub). The conjugated core structure represents moreover a chromophore with a high photosensitivity for (E,E) reversible arrow (E,Z) isomerization reactions: this property makes the compounds interesting for optical imaging and switching techniques. (c) 2008 Published by Elsevier Ltd.

  (E,E)-3,6-二联苯基吡喃系物(3a-t类)通过应用西格里反应制备，使用的底物是3,6-二甲基吡啶(13)和对应的亚胺4a-t或10a-t。这些变形色液态晶体相(N, S-A, S-B, S-C, S-E, S-1/F和 Cub)的交叉偶极矩导致它们展现出极强的自组织倾向，尤其是高热力学稳定性和极性。这些共轭中心结构也具有高感光性，尤其是对于(E,E)可逆逆向的(E,Z)异构转变反应，这种特性使其成为光学成像和转态切换技术中很有兴趣的研究对象。 (c) 2008 版权所有，Elsevier Ltd.
• (E,E,E)-4,4′-Distyrylstilbenes – Synthesis, Photophysics, Photochemistry and Phase Behavior
  作者：Herbert Meier、Thorsten Lifka、Ulf Stalmach、Annette Oehlhof、Sabine Prehl

  DOI：10.1002/ejoc.200701046

  日期：2008.3

  The fluorescence quantum yields F(n) of oligo[2,5-bis(propyloxy)-1,4-phenylenevinylene]s (1b) reach for the trimer (n = 3) in solution a maximum of 86 %, which is almost twice as high as for the monomer (n = 1) and the octamer or undecamer (n = 8, 11). The latter represent the convergence limit of 46 %. 4-Mono-, 3,4-di- or 3,4,5-trisubstituted terminal phenyl rings in the trimers 6a–f do not lead to

  寡聚[2,5-双(丙氧基)-1,4-亚苯基亚乙烯基]s (1b) 的荧光量子产率 F(n) 达到溶液中三聚体 (n = 3) 的最大值 86%，几乎是是单体 (n = 1) 和八聚体或十一聚体 (n = 8, 11) 的两倍。后者代表 46% 的收敛极限。三聚体 6a-f 中的 4-单-、3,4-二-或 3,4,5-三取代的末端苯环不会产生棒状或相粒状液晶；然而，使用己氧基 (6h) 甚至 OCH3 基团 (6g) 进行 2,3,4-三取代会影响 LC 的形成。用富含能量的紫外线照射会引起最初共轭链的交联。在 6c 的情况下，也可以建立化学和立体选择性 [2π + 2π] 光环加成。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008）
• Synthesis and Excited-State Properties of an Oligophenylenevinylene Heptamer Substituted with Two Fullerene Moieties
  作者：Jean-François Nierengarten、Nicola Armaroli、Aline Gégout、Teresa Figueira-Duarte、Andrea Listorti

  DOI：10.1055/s-2006-947327

  日期：2006.11

  An oligophenylenevinylene (OPV) derivative substituted with two fullerene subunits has been prepared starting from a fullerene carboxylic acid derivative and an OPV heptamer bearing two alcohol functions. Photophysical investigations have revealed the occurrence of intramolecular photoinduced energy- and electron-transfer processes in this hybrid compound.

  从富勒烯羧酸衍生物和带有两个醇官能团的 OPV 七聚体开始，制备了被两个富勒烯亚单元取代的低聚亚苯基亚乙烯基 (OPV) 衍生物。光物理研究揭示了在这种杂化化合物中发生了分子内光致能量和电子转移过程。
• Dodecyloxy-substituted 2,4,6-tris(styryl)pyridines
  作者：Thorsten Lifka、Annette Oehlhof、Herbert Meier

  DOI：10.1002/jhet.5570450346

  日期：2008.5

  (E,E,E)-2,4,6-Tris(styryl)pyridines 2a-c with 3, 6 or 9 dodecyloxy substituents were prepared by the highly stereoselective condensation reaction of collidine (8) and the corresponding phenyl-(1-phenyl-methylidene)amines 7a-c (Siegrist reaction). In contrast to the corresponding compounds with a benzene or a 1,3,5-triazine core, 2a-c do not show any hints for the formation of thermotropic liquid crystals

  通过可力丁（8）和相应的苯基-（1的高度立体选择性缩合反应，制备了具有3、6或9个十二烷氧基取代基的（E，E，E）-2,4,6-Tris（苯乙烯基）吡啶2a-c。-苯基亚甲基）胺7a-c（Siegrist反应）。与具有苯或1,3,5-三嗪核心的相应化合物相反，2a-c没有显示出形成热致液晶的任何提示。这种星形系统的主要应用是在非线性光学领域。