3,4,5-tris((S)-3,7-dimethyloctyloxy)benzaldehyde | 1214273-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4,5-tris((S)-3,7-dimethyloctyloxy)benzaldehyde
• 英文别名: 3,4,5-tris{(S)-3,7-dimethyloctyloxy}benzaldehyde
• CAS: 1214273-31-0
• 化学式: C₃₇H₆₆O₄
• 分子量: 574.929
• InChiKey: NXUXPAYRRMAUJZ-ZDCRTTOTSA-N

物化性质

• 沸点：
  626.3±50.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.19
• 重原子数：
  41.0
• 可旋转键数：
  25.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,4,5-tris((S)-3,7-dimethyloctyloxy)benzaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.08h， 生成 4-(4-((E)-4-((E)-3,4,5-tris(((S)-3,7-dimethyloctyl)oxy)styryl)styryl)phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole
  参考文献：
  名称：

  Steering the Conformation and Chiroptical Properties of Poly(dithienopyrrole)s Substituted with Chiral OPV Side Chains.

  摘要：

  This manuscript discusses the conformation and chiroptical properties of poly(dithienopyrrole)s (PDTPs), Substituted with oligo(phenylenevinylene) (OPV) side chains and the influence of the substitution of the OPV moiety on these features. The OPV side chains were equipped with gallic acid moieties in order to promote the formation of a helical conformation in poor solvents. The polymers were prepared by Stille-couplings and characterized by GPC and NMR, UV-vis, CID, and emission spectroscopy. It was found that OPV-PDTPs, solely equipped with (chiral) alkyl groups at the terminal gallic acid group, show a very strong tendency to adopt a helical conformation, but no resolution or the mixture of helices and therefore no chiral expression. Additional substitution of the allows for a discrimination of the mixture of lielical senses. In this way, the OPV side chains can bechirally organized by the helical PDTP backbone. Substitution of the OPV in a-position, however, sterically excludes the possibility to adopt a helical conformation, but results in a lamellar supramolecular Structure in poor solvents. The macromolecular behavior is explained in terms of space confinement and sieric hindrance in the respective Structures.

  DOI：

  10.1021/ma902762z
• 作为产物：
  描述：

  3,4,5-三羟基苯甲醛 在 palladium on activated charcoal 、 氢气 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3,4,5-tris((S)-3,7-dimethyloctyloxy)benzaldehyde
  参考文献：
  名称：

  Technologically promising, room temperature luminescent columnar liquid crystals derived from s-triazine core: molecular design, synthesis and characterization

  摘要：

  Three fold Horner-Wadsworth-Emmons (HWS) reaction of triphosphonate with achiral/chiral 3,4,5-tris(alkoxy)benzaldehydes yield novel achiral/chiral star-shaped liquid crystals (LCs), in which three fluorophore arms such as 1,2,3-tris(alkoxy)-5-styrylbenzenes are tethered to a central s-triazine core. These LCs, the first of their kind, display a columnar liquid crystalline phase over a wide temperature range existing between well below and above the room temperature, which is evidenced by optical and calorimetric studies. Besides, they show photoluminescence both in solution and mesomorphic states. Thus, given their self-organization into fluid one-dimensional columnar array coupled with light generating capability, these organic ordered-fluids can be regarded as novel media for advanced technological applications. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.010

文献信息

• Supramolecular Columnar Liquid Crystals with Tapered-Shape Simple Pyrazoles Obtained by Efficient Henry/Michael Reactions
  作者：Hugo Blanco、Verónica Iguarbe、Joaquín Barberá、José Luis Serrano、Anabel Elduque、Raquel Giménez

  DOI：10.1002/chem.201504779

  日期：2016.3.24

  novel supramolecular liquid crystals. The mesogens are fluorescent 3,5‐dimethyl‐4‐(di or trialkoxyphenyl)pyrazoles and, in spite of the tapered shape of these molecules and their structural simplicity (only one phenyl ring), columnar liquid‐crystal phases were formed that are stable at room temperature. The self‐assembled structure was studied by XRD and the columnar cross section contains two molecules

  通过有效的亨利和迈克尔反应的结合，从苯甲醛开始的介晶吡唑的直接合成导致了新型的超分子液晶。介晶是荧光3,5-二甲基-4-（二或三烷氧基苯基）吡唑，尽管这些分子呈锥形且结构简单（仅一个苯环），但仍形成了稳定的柱状液晶相在室温下。X射线衍射研究了自组装结构，柱状截面平均包含两个分子，吡唑通过氢键相互作用呈反平行排列。相反，三甲氧基类似物的单晶结构没有显示氢键合的吡唑，而是头到尾排列的分子链。
• Self-adjusted aromatic cation-π binding promotes controlled self-assembly of positively charged π-electronic molecules
  作者：Zhelin Zhang、Bin Mu、Xiaohe Miao、Liang Wang、Huanjun Lu、Yue Ma、Wei Tian

  DOI：10.1016/j.chempr.2024.01.026

  日期：2024.4

  binding interactions that govern the self-assembly direction, resulting in positively charged columnar assemblies. The obtained columnar structures are controlled by the self-adjustment process inherent in the specific aromatic cation-π binding modes. We characterize the transition from alternate overlapping to helical stacking, which ultimately yields thermodynamically favorable columnar polymorphism

  带相同电荷的 π 电子分子的自组装产生独特的带电组装体，其特性在相应的电子中性类似物中未观察到。然而，相反电荷之间的静电吸引力通常会导致逐个电荷的组装，从而阻碍所需功能的表现。在此，我们提出了一种自我调节的芳香族阳离子-π结合策略来应对这一挑战。所述方法涉及一种自互补设计，其特征是双位点芳香族阳离子-π结合相互作用控制自组装方向，从而产生带正电的柱状组装体。所获得的柱状结构由特定芳香族阳离子-π结合模式固有的自我调节过程控制。我们描述了从交替重叠到螺旋堆叠的转变，最终产生热力学上有利的柱状多态性，包括具有可调节的柱内/柱间相关性的分子晶体和液晶。这些带电柱状组件充当高效的内在CO 2还原光催化剂。螺旋堆叠的柱状组件表现出增强的性能，从而凸显了分子堆叠模式对光催化效率的深远影响。
• Study of the aggregation behavior of a π-conjugated dendrimer with a twisted core
  作者：Joaquín C. García-Martínez、Enrique Díez-Barra、Julián Rodríguez-López

  DOI：10.1016/j.tetlet.2012.03.095

  日期：2012.5

  A dendrimer having phenylene vinylene and phenylene ethynylene moieties, a twisted core, and eighteen chiral centers on the periphery has been prepared in high yield by using Sonogashira and Horner-Wadsworth-Emmons reactions. UV-visible and fluorescence spectra and circular dichroism measurements have been envisaged to study the aggregation behavior. (C) 2012 Elsevier Ltd. All rights reserved.