2'-carboxy-4,4''-bis(trimethylsilylethynyl)-5'-(1-octynyl)-1,1':3',1''-terphenyl | 1034710-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2'-carboxy-4,4''-bis(trimethylsilylethynyl)-5'-(1-octynyl)-1,1':3',1''-terphenyl
• 英文别名: 4-Oct-1-ynyl-2,6-bis[4-(2-trimethylsilylethynyl)phenyl]benzoic acid；4-oct-1-ynyl-2,6-bis[4-(2-trimethylsilylethynyl)phenyl]benzoic acid
• CAS: 1034710-63-8
• 化学式: C₃₇H₄₂O₂Si₂
• 分子量: 574.91
• InChiKey: DUZUFGDAPLDDPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2'-carboxy-4,4''-bis(trimethylsilylethynyl)-5'-(1-octynyl)-1,1':3',1''-terphenyl 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 2'-carboxy-4,4''-bis(ethynyl)-5'-(1-octynyl)-1,1':3',1''-terphenyl 、 2'-carboxy-4-ethynyl-4''-trimethylsilylethynyl-5'-(1-octynyl)-1,1':3',1''-terphenyl
  参考文献：
  名称：

  带有羧基的共轭聚合物的同质双螺旋的形成和夹在链间的手性胺对大分子螺旋度的放大作用

  摘要：

  夹心胺：具有羧基的π共轭聚合物可自缔合形成消旋双螺旋。相反，与手性胺形成一个独特的单手双螺旋，其中的链通过环状氢键网络将成对的手性胺夹在中间（见图）。胺的手性信息随着螺旋手性的显着放大而转移到聚合物主链上。

  DOI：

  10.1002/anie.201301005
• 作为产物：
  描述：

  1,3-二氯-5-(1-辛炔基)苯 、 二氧化碳 、 4-(trimethylsilylethynyl)phenylmagnesium bromide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.5h， 以25%的产率得到2'-carboxy-4,4''-bis(trimethylsilylethynyl)-5'-(1-octynyl)-1,1':3',1''-terphenyl
  参考文献：
  名称：

  Double-Stranded Helical Polymers Consisting of Complementary Homopolymers

  摘要：

  Two complementary homopolymers of chiral amidines and achiral carboxylic acids with m-terphenyl-based backbones were synthesized by the copolymerization of a p-diiodobenzene derivative with the diethynyl monomers bearing a chiral amidine group and a carboxyl group using the Sonogashira reaction, respectively. Upon mixing in THF, the homopolymer strands assembled into a preferred-handed double helix through interstrand amidinium-carboxylate salt bridges, as evidenced by its absorption, circular dichroism, and IR spectra. In contrast, when mixed in less polar solvents, such as chloroform, the complementary strands kinetically formed an interpolymer complex with an imperfect double helical structure containing a randomly hybridized cross-linked structure, probably because of strong salt bridge formations. This primary complex was rearranged into the fully double helical structure by treatment with a strong acid followed by neutralization with an amine. High-resolution atomic force microscopy revealed the double-stranded helical structure and enabled the determination of the helical sense.

  DOI：

  10.1021/ja711447s

文献信息

• Photocontrolled template-directed synthesis of complementary double helices assisted by amidinium–carboxylate salt bridge formation
  作者：Junki Tanabe、Daisuke Taura、Hidekazu Yamada、Yoshio Furusho、Eiji Yashima

  DOI：10.1039/c3sc50833a

  日期：——

  chloroform in the presence of the corresponding optically inactive carboxylic acid dimer or optically active amidine dimer linked by a trans-azobenzene unit as the template, respectively. The cis-azobenzene-linked carboxylic acid template markedly slowed the monomer conversions, and hence a reversible photocontrolled dimerization was achieved by light-induced cis–trans isomerization upon alternative

  在一个末端带有甲酰基或氨基的手性or或非手性羧酸单体之间的模板指导的亚胺键形成反应显着地加速了34倍或10倍。 氯仿在分别以反式-偶氮苯单元为模板连接的相应的旋光性羧酸二聚体或旋光性am二聚体的存在下。所述顺-azobenzene联羧酸模板显着减缓了单体转化率，且因此可逆photocontrolled二聚化，通过光诱导的实现顺-反式在与UV和可见光照射替代异构化。
• Double-Stranded Helical Polymers Consisting of Complementary Homopolymers
  作者：Takeshi Maeda、Yoshio Furusho、Shin-Ichiro Sakurai、Jiro Kumaki、Kento Okoshi、Eiji Yashima

  DOI：10.1021/ja711447s

  日期：2008.6.1

  Two complementary homopolymers of chiral amidines and achiral carboxylic acids with m-terphenyl-based backbones were synthesized by the copolymerization of a p-diiodobenzene derivative with the diethynyl monomers bearing a chiral amidine group and a carboxyl group using the Sonogashira reaction, respectively. Upon mixing in THF, the homopolymer strands assembled into a preferred-handed double helix through interstrand amidinium-carboxylate salt bridges, as evidenced by its absorption, circular dichroism, and IR spectra. In contrast, when mixed in less polar solvents, such as chloroform, the complementary strands kinetically formed an interpolymer complex with an imperfect double helical structure containing a randomly hybridized cross-linked structure, probably because of strong salt bridge formations. This primary complex was rearranged into the fully double helical structure by treatment with a strong acid followed by neutralization with an amine. High-resolution atomic force microscopy revealed the double-stranded helical structure and enabled the determination of the helical sense.
• Formation of a Homo Double Helix of a Conjugated Polymer with Carboxy Groups and Amplification of the Macromolecular Helicity by Chiral Amines Sandwiched between the Strands
  作者：Wataru Makiguchi、Shinzo Kobayashi、Yoshio Furusho、Eiji Yashima

  DOI：10.1002/anie.201301005

  日期：2013.5.10

  Sandwiched amines: A π‐conjugated polymer with carboxy groups self‐associates to form a racemic double helix. In contrast, with chiral amines it forms a unique one‐handed double helix, in which the strands sandwich pairs of chiral amines through cyclic hydrogen‐bonding networks (see picture). The chiral information of the amines is transferred to the polymer backbones with remarkable amplification

  夹心胺：具有羧基的π共轭聚合物可自缔合形成消旋双螺旋。相反，与手性胺形成一个独特的单手双螺旋，其中的链通过环状氢键网络将成对的手性胺夹在中间（见图）。胺的手性信息随着螺旋手性的显着放大而转移到聚合物主链上。