3,4,5-三[3,4,5-三(十二烷氧基)苄甲氧基]苯甲酸 | 186031-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4,5-三[3,4,5-三(十二烷氧基)苄甲氧基]苯甲酸
• 英文名称: 3,4,5-Tris[3',4',5'-trse-(n-dodecan-1-yloxy)benzyloxy]benzoic acid
• 英文别名: 3,4,5-tris[3',4',5'-tris(n-dodecan-1-yloxy)benzyloxy]benzoic acid；3,4,5-tris(3',4',5'-tris(dodecan-1-yloxy)benzyloxy)benzoic acid；Benzoic acid, 3,4,5-tris[[3,4,5-tris(dodecyloxy)phenyl]methoxy]-；3,4,5-tris[(3,4,5-tridodecoxyphenyl)methoxy]benzoic acid
• CAS: 186031-59-4
• 化学式: C₁₃₆H₂₄₀O₁₄
• 分子量: 2099.39
• InChiKey: GXPZLCQWWYDLFF-UHFFFAOYSA-N

物化性质

• 沸点：
  1424.7±60.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  55.8
• 重原子数：
  150
• 可旋转键数：
  118
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  14

安全信息

• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  3,4,5-三[3,4,5-三(十二烷氧基)苄甲氧基]苯甲酸 、 三乙二醇 在 4-二甲氨基吡啶 、 四丁基氢氧化铵 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以50%的产率得到Triethyleneglycol[3,4,5-tris{3',4',5'-tris(n-dodecane-1-yloxy)benzyloxy}benzoate]
  参考文献：
  名称：

  Ungar, Goran; Percec, Virgil; Holerca, Marian N., Chemistry - A European Journal, 2000, vol. 6, # 7, p. 1258 - 1266

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3,4,5-tris[3',4',5'-tris(n-dodecan-1-yloxy)benzyloxy]benzoate 在 水 、 potassium hydroxide 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以88%的产率得到3,4,5-三[3,4,5-三(十二烷氧基)苄甲氧基]苯甲酸
  参考文献：
  名称：

  通过修饰其脂族与芳族体积比来阐明超分子树状聚合物的Pm $ \ bar 3 $ n立方相的结构

  摘要：

  报道了自组装成球形超分子树状大分子的第二代圆锥形树突的文库的合成，结构和逆向结构分析。该文库由具有包含4至16个碳原子的n烷基的两亲树突组成。在其正烷基中含有6至16个碳原子的树枝状分子自组装成球形超分子树枝状大分子，这些树枝状大分子在Pm n立方晶格中自组织。Pm n的结构和后结构分析由超分子树枝状聚合物产生的晶格表明，球形树枝状聚合物的芳族核的体积不取决于其烷基中碳原子的数目。该结果促进了球形超分子树状大分子的脂族和芳族域的绝对电子密度的平均值的计算。所述的较高阶的衍射峰的相对强度PM Ñ晶格随着由碳原子数在介导球体的脂族部分的体积Ñ -烷基基团减少。这项研究表明Pm n高阶衍射峰的相对强度最大增加 非空心超分子树状聚合物产生的晶格。

  DOI：

  10.1002/chem.200901324

文献信息

• Synthesis, Structural Analysis, and Visualization of a Library of Dendronized Polyphenylacetylenes
  作者：Virgil Percec、Jonathan G. Rudick、Mihai Peterca、Sasha R. Staley、Martin Wagner、Makoto Obata、Catherine M. Mitchell、Wook-Dong Cho、Venkatachalapathy S. K. Balagurusamy、James N. Lowe、Martin Glodde、Oliver Weichold、Kyung J. Chung、Nicholas Ghionni、Sergei N. Magonov、Paul A. Heiney

  DOI：10.1002/chem.200600009

  日期：2006.7.24

  A library of eleven high cis-content cis-transoidal polyphenylacetylenes (PPAs) dendronized with self-assembling dendrons was prepared from a library of fifteen convergently synthesized macromonomers. Using [Rh(C triple bond CPh)(nbd)(PPh(3))(2)] (nbd=2,5-norbornadiene) in the presence of 10 equiv of N,N-dimethylaminopyridine, predictive control over molecular weight and narrow molecular weight distribution

  从十五个聚合合成的大分子单体的文库中制备了用自组装树状体进行树状化的十一个高顺式含量的顺式-反式-聚苯乙炔（PPA）库。在10当量的N，N-二甲基氨基吡啶存在下使用[Rh（C三键CPh）（nbd）（PPh（3））（2）]（nbd = 2,5-降冰片二烯），可预测地控制分子量和获得窄的分子量分布。PPA骨架充当自组装树突的螺旋支架。树突的主要结构决定了通过X射线衍射（XRD）确定的自组织六边形柱状（Phi（h））晶格以及高度有序的热解石墨（HOPG）和云母通过原子力显微镜（AFM）可视化。
• Synthesis and NaOTf Mediated Self-Assembly of Monodendritic Crown Ethers
  作者：Virgil Percec、Wook-Dong Cho、Goran Ungar、Duncan J. P. Yeardley

  DOI：10.1002/1521-3765(20020503)8:9<2011::aid-chem2011>3.0.co;2-3

  日期：2002.5.3

  parallel-piped monodendrons; c) no effect on the stability of the two-dimensional S(B) phase generated from parallel-piped monodendrons; d) stabilization of the two-dimensional p6mm hexagonal columnar phase self-organized from cylindrical supramolecular dendrimers that are self-assembled from tapered monodendrons; and e) destabilization of the two-dimensional p6mm hexagonal columnar phase self-organized from

  提出了十个以苯并[15] crown-5为基点的基于苄基醚的自组装单树枝状分子的合成。这些树状结构单元直接或通过与NaOTf络合在二维近晶B，近晶A和p6mm六角柱状（Phi（h））和三维Pm3n立方晶格中自组装。通过X射线衍射实验对这些晶格以及在相同焦点处由包含其他功能基团的相同单枝分子生成的晶格进行结构分析，首次提供了分子结构与单枝分子形状，超分子树状大分子和晶格的对称性。已显示与NaOTf的络合提供以下五个不同趋势：a）由球状树枝状分子自组织的三维Pm3n立方晶格的稳定性，球状树枝状分子由圆锥单枝状分子自组装而成；b）稳定由平行管单枝形成的二维S（A）相；c）对由平行管单枝生成的二维S（B）相的稳定性没有影响；d）由圆柱形超分子树枝状分子自组织的二维p6mm六角形柱状相的稳定化，该圆柱状超分子树枝状分子是由锥形单树枝状分子自组装而成的；e）由半盘单树枝状分子自组装的圆柱超分子树枝状分
• Self-assembly of dendron-helical polypeptide copolymers: organogels and lyotropic liquid crystals
  作者：Kyoung Taek Kim、Chiyoung Park、Chulhee Kim、Mitchell A. Winnik、Ian Manners

  DOI：10.1039/b516625j

  日期：——

  New macromolecular self-assembling building blocks, dendron-helical polypeptide copolymers, have been synthesized; these materials possess a well-defined 3-D shape and self-assemble in solution to form nanoribbon and lyotropic liquid crystalline phases.

  我们合成了新的大分子自组装构建模块--树枝状螺旋形多肽共聚物；这些材料具有明确的三维形状，并能在溶液中自组装，形成纳米带和各向同性液晶相。
• A linear conjugated core for functional columnar liquid crystals
  作者：Ana Pérez、José Luis Serrano、Teresa Sierra、Alfredo Ballesteros、Diana de Saá、Roberto Termine、Upendra Kumar Pandey、Attilio Golemme

  DOI：10.1039/c2nj20950k

  日期：——

  Two series of polycatenar molecules consisting of a π-conjugated rigid core derived from 3-hexen-1,5-diyne coupled to different types of benzoic acid derivatives have been prepared and their potential as multifunctional materials has been investigated. The size ratio between the rigid core and the benzoate-derived groups, which vary in bulk, is crucial to address self-organization, thus indicating the delicate balance of forces involved in liquid crystalline (LC) behaviour. LC nematic, crystalline or LC columnar behaviour is observed depending on the structure of the benzoate moiety. Hexagonal two-dimensional columnar organization is attained for mesogens with benzoate-derived groups bearing six and nine alkoxylic tails. The stacking unit of the columnar organizations is different depending on the total number of tails, twelve or eighteen, with two molecules and half a molecule per columnar stratum, respectively. Macroscopic properties related to molecular structure, such as luminescence, chirality and electroactivity, have also been studied. Luminescent behaviour is observed for all mesogenic materials, which show higher Stokes shifts than in solution. In addition, supramolecular chirality in the mesophase has been observed for a chiral mesogen. Finally, the photoconducting behaviour of two of the columnar materials has been evaluated.

  我们制备了两个系列的聚卡替那尔分子，它们由源自 3-己烯-1,5-二炔的 π-共轭刚性核心和不同类型的苯甲酸衍生物组成，并研究了它们作为多功能材料的潜力。刚性内核与苯甲酸衍生物基团之间的尺寸比（在体积上有所不同）对于解决自组织问题至关重要，从而表明了液晶（LC）行为中所涉及的力的微妙平衡。根据苯甲酸酯分子结构的不同，可观察到液晶向列、结晶或液晶柱状行为。带有六个和九个烷氧基尾部的苯甲酸酯衍生基团的中间体可形成六角形的二维柱状组织。柱状组织的堆积单位因尾部总数（12 或 18）而异，每个柱状层分别有两个分子和半个分子。我们还研究了与分子结构有关的宏观特性，如发光、手性和电活性。所有介生材料都能发光，并显示出比溶液中更高的斯托克斯位移。此外，还观察到一种手性介原在介相中具有超分子手性。最后，还对两种柱状材料的光电导行为进行了评估。
• Rational Design of the First Spherical Supramolecular Dendrimers Self-Organized in a Novel Thermotropic Cubic Liquid-Crystalline Phase and the Determination of Their Shape by X-ray Analysis
  作者：V. S. K. Balagurusamy、G. Ungar、V. Percec、G. Johansson

  DOI：10.1021/ja963295i

  日期：1997.2.1

  The rational design, the synthesis via a new convergent approach, and the characterization of four generations of monodendrons based on the AB(3) building block methyl 3,4,5-trishydroxybenzoate are described. The first generation monodendrons are crystalline. The second generation methyl 3,4,5-tris-3',4',5'-[tris(n-dodecyloxy)benzyloxy]benzoate (12Gn-AG-CH3, n = 2), the corresponding benzyl alcohol (12G2-AG-CH2OH) and benzoic acid (12G2-AG), and all higher generation monodendrons with n = 3 and 4 exhibit in addition to the crystal phase an isomorphous cubic liquid-crystalline (LC) phase of space group. The cubic unit cell parameters of 12G2-AG, 12G3-AG, and 12G4-AG are 68.3, 79.2, and 84.0 Angstrom, respectively. Computed electron density profiles demonstrated that in the cubic phase 12, 6, and 2 monodendrons of generation 2, 3 and 4 are self-assembled in supramolecular dendrimers resembling spherical micelles when they are centered at the corners and the body-center and respectively highly rounded tetrahedra when they are at 1/4 and 3/4 distance along one of the bisectors of each face of the cubic cell. This novel thermotropic LC phase is similar to that of the lyotropic phase of biological lipids. These supramolecular dendrimers contain a poly(benzyl ether) core dispersed in an aliphatic matrix of nearly uniform density which is made up of the melted terminal long alkyl chains of the monodendrons. The size of the supramolecular dendrimer and of the entire unit cell increases with generation number as a result of a disproportionately large increase in the number of AB(3) repeat units relative to the number of terminal alkyl chains in a monodendron which decreases its average cone angle. The present experiments provide the first examples of monodendrons which self-assemble into spherical supramolecular dendrimers forming a thermotropic cubic LC phase.