4-[4-(4-Hexoxyphenyl)buta-1,3-diynyl]phenol | 265653-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[4-(4-Hexoxyphenyl)buta-1,3-diynyl]phenol
• 英文别名: 4-[4-(4-hexoxyphenyl)buta-1,3-diynyl]phenol
• CAS: 265653-41-6
• 化学式: C₂₂H₂₂O₂
• 分子量: 318.415
• InChiKey: DUFDOOICWRKTTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[4-(4-Hexoxyphenyl)buta-1,3-diynyl]phenol 在 potassium carbonate 、 potassium hydroxide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 14.0h， 生成 1-[6-[4-[4-(4-Hexoxyphenyl)buta-1,3-diynyl]phenoxy]hexyl]imidazole
  参考文献：
  名称：

  Unimolecular Photopolymerization of High-Emissive Materials on Cylindrical Self-Assemblies

  摘要：

  We report a novel self-assembly pathway from a bis(imidazolyl) diphenyl-diacetylene (DPDA) compound as a realization of self-templated photopolymerization with high polymerization degrees. The work takes advantage of a cylindrical self-assembly that strengthens the preorganization of the diphenyl-diacetylene moiety at the single molecular level. On this basis, photopolymerization of DPDA can be conducted smoothly to form high-molecular-weight polydiphenyl diacetylene. Such a cylindrical self-assembly is highly dependent on molecular structure, and control studies show that only oligomers can be formed on random self-assemblies from a monoimidazolyl or nonimidazolyl diphenyl-diacetylene compound. Moreover, the cylindrical self-assembly based systems bear aggregation-induced emission enhancement characteristics and are solution processable. The leading thin-film could afford a selectively tunable function in luminescent micropatterns.

  DOI：

  10.1021/acs.macromol.5b01488
• 作为产物：
  描述：

  溴己烷 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 4-[4-(4-Hexoxyphenyl)buta-1,3-diynyl]phenol
  参考文献：
  名称：

  Phenoxide-mediated Sonogashira coupling of trimethylsilylalkynes and aryliodides: practical synthesis of phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes

  摘要：

  We successfully synthesized phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes from trimethylsilylalkynes and aryliodides via silyl-group-migration-induced deprotection of alkynes and the usual Sonogashira coupling. The phenol moiety, which works as a desilylating agent, can be attached to any position in the coupling partner. This improvement for Sonogashira coupling would be highly effective, especially when the coupling partner has a phenol moiety. Additionally, the stability of the migrated silyl moiety on the ethynylation of 2-iodophenol is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.091

文献信息

• Engineering Topochemical Polymerizations Using Block Copolymer Templates
  作者：Liangliang Zhu、Helen Tran、Frederick L. Beyer、Scott D. Walck、Xin Li、Hans Ågren、Kato L. Killops、Luis M. Campos

  DOI：10.1021/ja507318u

  日期：2014.9.24

  With the aim to achieve rapid and efficient topochemical polymerizations in the solid state, via solution-based processing of thin films, we report the integration of a diphenyldiacetylene monomer and a poly(styrene-b-acrylic acid) block copolymer template for the generation of supramolecular architectural photopolymerizable materials. This strategy takes advantage of non-covalent interactions to template a topochemical photopolymerization that yields a polydiphenyldiacetylene (PDPDA) derivative. In thin films, it was found that hierarchical self-assembly of the diacetylene monomers by microphase segregation of the block copolymer template enhances the topochemical photopolymerization, which is complete within a 20 s exposure to UV light. Moreover, UV-active cross-linkable groups were incorporated within the block copolymer template to create micropatterns of PDPDA by photolithography, in the same step as the polymerization reaction. The materials design and processing may find potential uses in the microfabrication of sensors and other important areas that benefit from solution-based processing of flexible conjugated materials.
• Phenoxide-mediated Sonogashira coupling of trimethylsilylalkynes and aryliodides: practical synthesis of phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes
  作者：Masayuki Shigeta、Junji Watanabe、Gen-ichi Konishi

  DOI：10.1016/j.tetlet.2013.01.091

  日期：2013.3

  We successfully synthesized phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes from trimethylsilylalkynes and aryliodides via silyl-group-migration-induced deprotection of alkynes and the usual Sonogashira coupling. The phenol moiety, which works as a desilylating agent, can be attached to any position in the coupling partner. This improvement for Sonogashira coupling would be highly effective, especially when the coupling partner has a phenol moiety. Additionally, the stability of the migrated silyl moiety on the ethynylation of 2-iodophenol is discussed. (C) 2013 Elsevier Ltd. All rights reserved.
• Unimolecular Photopolymerization of High-Emissive Materials on Cylindrical Self-Assemblies
  作者：Liangliang Zhu、Xin Li、Samuel N. Sanders、Hans Ågren

  DOI：10.1021/acs.macromol.5b01488

  日期：2015.8.11

  We report a novel self-assembly pathway from a bis(imidazolyl) diphenyl-diacetylene (DPDA) compound as a realization of self-templated photopolymerization with high polymerization degrees. The work takes advantage of a cylindrical self-assembly that strengthens the preorganization of the diphenyl-diacetylene moiety at the single molecular level. On this basis, photopolymerization of DPDA can be conducted smoothly to form high-molecular-weight polydiphenyl diacetylene. Such a cylindrical self-assembly is highly dependent on molecular structure, and control studies show that only oligomers can be formed on random self-assemblies from a monoimidazolyl or nonimidazolyl diphenyl-diacetylene compound. Moreover, the cylindrical self-assembly based systems bear aggregation-induced emission enhancement characteristics and are solution processable. The leading thin-film could afford a selectively tunable function in luminescent micropatterns.