1-<4-<2-(2-hydroxyethoxy)ethoxy>styryl>-4-(4-decylsulfonylstyryl)benzene | 444727-37-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-<4-<2-(2-hydroxyethoxy)ethoxy>styryl>-4-(4-decylsulfonylstyryl)benzene
• 英文别名: 1-{4-[2-(2-hydroxyethoxy)ethoxy]styryl}-4-(4-decylsulfonylstyryl)benzene；2-[2-[4-[(E)-2-[4-[(E)-2-(4-decylsulfonylphenyl)ethenyl]phenyl]ethenyl]phenoxy]ethoxy]ethanol
• CAS: 444727-37-1
• 化学式: C₃₆H₄₆O₅S
• 分子量: 590.824
• InChiKey: YRBCGQSJXYZOFX-YXLFCKQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  42
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基丙烯酸酐 、 1-<4-<2-(2-hydroxyethoxy)ethoxy>styryl>-4-(4-decylsulfonylstyryl)benzene 在 4-二甲氨基吡啶 、 4,4'-硫联二(6-叔丁基-2-甲基苯酚) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到2-methyl-2-propenoic acid 2-{2-{4-{2-{4-{2-[4-(decylsulfonyl)phenyl]ethenyl}phenyl}ethenyl}phenoxy}ethoxy}ethyl ester
  参考文献：
  名称：

  Synthesis and properties of highly soluble third-order optically nonlinear chromophores and methacrylate monomer based on distyrylbenzene

  摘要：

  以立体选择性 Wadsworth-Emmons 反应为关键步骤，合成了一系列新型高溶解性二丙烯苯，这些二丙烯苯带有聚（烷氧基）和/或烷基磺酰基增溶取代基。相应的 4,4′-二取代二丙烯酰基聚（烷氧基）烷基磺酰基已与丙烯酸单体共价结合，并成功地与甲基丙烯酸甲酯（MMA）共聚。所有 4,4′-二取代二丙烯酰苯和基于聚丙烯酸酯的共聚物都表现出优异的溶解性、加工性和热稳定性。重要的是，与相应的对称 4,4′-二取代二丙烯苯相比，2-（2-丁氧基乙氧基）乙氧基-己基磺酰基 4,4′-二取代二丙烯苯的吸收最大值仅有轻微的浴色偏移；然而，在 800 纳米波长处通过 Z 扫描测量得出的三阶光学非线性大约是对称的 4,4′-二取代二丙烯苯的两倍。

  DOI：

  10.1039/a803229g
• 作为产物：
  描述：

  1-癸硫醇 在 lithium aluminium tetrahydride 、 sodium hydride 、 sodium carbonate 、 triphenylphosphine dibromide 1:1 addition complex 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 1-<4-<2-(2-hydroxyethoxy)ethoxy>styryl>-4-(4-decylsulfonylstyryl)benzene
  参考文献：
  名称：

  Synthesis and optical characterization of unsymmetrical oligophenylenevinylenes

  摘要：

  An efficient route to highly soluble unsymmetrical oligo(phenylenevinylenes) (OPVs) has been developed. The OPVs are end-substituted with donor alkoxy and acceptor sulfonyl groups for charge polarization and incorporate a methacrylate unit suitable for co-polymerization. The absorption and excitation spectra of the OPVs and their precursors have been examined; vibronic features are noted, and pi-system lengthening and introduction of polarizing substituents red-shift the spectral maxima. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00003-0

文献信息

• Synthesis and properties of highly soluble third-order optically nonlinear chromophores and methacrylate monomer based on distyrylbenzene
  作者：M. S. Wong、M. Samoc、A. Samoc、B. Luther-davies、M. G. Humphrey

  DOI：10.1039/a803229g

  日期：——

  A novel series of highly soluble distyrylbenzenes bearing poly(alkyleneoxy) and/or alkylsulfonyl solubilizing substituents has been synthesized using the stereoselective Wadsworth–Emmons reaction as a key step. The corresponding poly(alkyleneoxy) alkylsulfonyl 4,4′-disubstituted distyrylbenzene has been covalently incorporated into an acrylic monomer which has also been successfully co-polymerized with methyl methacrylate (MMA). All the 4,4′-disubstituted distyrylbenzenes and the polyacrylate based co-polymer show excellent solubility, processibility and thermal stability. Importantly, 2-(2-butoxyethoxy)ethoxy-hexylsulfonyl 4,4′-disubstituted distyrylbenzene exhibits only a minor bathochromic shift of the absorption maximum compared to those of the corresponding symmetrically 4,4′-disubstituted distyrylbenzenes; however, its third-order optical nonlinearity derived from Z-scan measurements at 800 nm is approximately twice as large as those of its symmetrically 4,4′-disubstituted counterparts.

  以立体选择性 Wadsworth-Emmons 反应为关键步骤，合成了一系列新型高溶解性二丙烯苯，这些二丙烯苯带有聚（烷氧基）和/或烷基磺酰基增溶取代基。相应的 4,4′-二取代二丙烯酰基聚（烷氧基）烷基磺酰基已与丙烯酸单体共价结合，并成功地与甲基丙烯酸甲酯（MMA）共聚。所有 4,4′-二取代二丙烯酰苯和基于聚丙烯酸酯的共聚物都表现出优异的溶解性、加工性和热稳定性。重要的是，与相应的对称 4,4′-二取代二丙烯苯相比，2-（2-丁氧基乙氧基）乙氧基-己基磺酰基 4,4′-二取代二丙烯苯的吸收最大值仅有轻微的浴色偏移；然而，在 800 纳米波长处通过 Z 扫描测量得出的三阶光学非线性大约是对称的 4,4′-二取代二丙烯苯的两倍。
• Synthesis and optical characterization of unsymmetrical oligophenylenevinylenes
  作者：Anke C Freydank、Mark G Humphrey、Reiner W Friedrich、Barry Luther-Davies

  DOI：10.1016/s0040-4020(02)00003-0

  日期：2002.2

  An efficient route to highly soluble unsymmetrical oligo(phenylenevinylenes) (OPVs) has been developed. The OPVs are end-substituted with donor alkoxy and acceptor sulfonyl groups for charge polarization and incorporate a methacrylate unit suitable for co-polymerization. The absorption and excitation spectra of the OPVs and their precursors have been examined; vibronic features are noted, and pi-system lengthening and introduction of polarizing substituents red-shift the spectral maxima. (C) 2002 Elsevier Science Ltd. All rights reserved.