2,6-bis[2-(1,5-di-n-hexyloxy-5-formyl-2-naphthyl)vinyl]-1,5-di-n-hexyloxynaphthalene | 222720-49-2

• 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: 2,6-bis[2-(1,5-di-n-hexyloxy-5-formyl-2-naphthyl)vinyl]-1,5-di-n-hexyloxynaphthalene
• 英文别名: 6-[(E)-2-[6-[(E)-2-(6-formyl-1,5-dihexoxynaphthalen-2-yl)ethenyl]-1,5-dihexoxynaphthalen-2-yl]ethenyl]-1,5-dihexoxynaphthalene-2-carbaldehyde
• CAS: 222720-49-2
• 化学式: C₇₂H₉₆O₈
• 分子量: 1089.55
• InChiKey: FNLLFGLEZZWNRW-FMWAKIAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23
• 重原子数：
  80
• 可旋转键数：
  42
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-bis[2-(1,5-di-n-hexyloxy-5-formyl-2-naphthyl)vinyl]-1,5-di-n-hexyloxynaphthalene 、 6-cyanomethyl-2-dodecyloxynaphthalene 在 potassium tert-butylate 、 四丁基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 、 叔丁醇 为溶剂， 反应 0.5h， 以92%的产率得到(Z)-3-[6-[(E)-2-[6-[(E)-2-[6-[(Z)-2-cyano-2-(6-dodecoxynaphthalen-2-yl)ethenyl]-1,5-dihexoxynaphthalen-2-yl]ethenyl]-1,5-dihexoxynaphthalen-2-yl]ethenyl]-1,5-dihexoxynaphthalen-2-yl]-2-(6-dodecoxynaphthalen-2-yl)prop-2-enenitrile
  参考文献：
  名称：

  Synthesis and Characterization of Novel Optically Active Polyarylene Vinylenes with Controlled Effective Conjugation Length

  摘要：

  New chiral and soluble binaphthyl derivatives (12 and 13) endowed with carboxaldehyde or cyanomethyl functional groups have been prepared as suitable building blocks for the synthesis by Knoevenagel condensation of a series of optically active block copolymers (1-7) with controlled effective conjugation length. A variety of functionalized co-monomers (14-19) have been prepared by different synthetic procedures to be used in further polymerization reactions with binaphthyl derivatives 12 and 13. Depending upon the nature of the co-monomers, it is possible to tune the wavelength of the new polymers, which is very close to that of the respective repeating units. Fluorescence measurements on polymers 1-3 reveal a strong blue-green emission with Stokes shifts of 74-107 nm. Theoretical calculations at the semiempirical AM-1 level have been carried out on model compounds, and the calculated torsion angles are in agreement with the electronic spectra data. Finally, the redox properties of the polymers prepared (1-7) were determined by cyclic voltammetry, and an amphoteric behavior with oxidation potentials ranging from 1.1 to 1.6 V and reduction potentials close to -1.5 V was found.

  DOI：

  10.1021/jo000761k
• 作为产物：
  描述：

  6-[(E)-2-[6-[(E)-2-(6-cyano-1,5-dihexoxynaphthalen-2-yl)ethenyl]-1,5-dihexoxynaphthalen-2-yl]ethenyl]-1,5-dihexoxynaphthalene-2-carbonitrile 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 以57%的产率得到2,6-bis[2-(1,5-di-n-hexyloxy-5-formyl-2-naphthyl)vinyl]-1,5-di-n-hexyloxynaphthalene
  参考文献：
  名称：

  Oligo-2,6-naphthylenevinylenes – 用于制备光致发光聚合物材料的新构件

  摘要：

  提出了适当的萘环对称和不对称官能化的合成策略。通过 Knoevenagel 和 Wittig 缩合反应，合成了新的荧光、不同功能化的低聚（2,6-亚萘基亚乙烯基），末端醛或溴取代的存在为将荧光三聚体掺入各种聚合物材料开辟了道路. 从结构的角度研究了在亚芳基亚乙烯基型材料中用体积更大的二烷氧基萘体系取代亚苯基环的效果，以及通过引入亚萘基亚乙烯基和氰基取代的亚萘基亚乙烯基单元来调节发射颜色和电子亲和力的可能性。也进行了调查。

  DOI：

  10.1002/(sici)1099-0690(199903)1999:3<643::aid-ejoc643>3.0.co;2-v

文献信息

• Oligo-2,6-naphthylenevinylenes – New Building Blocks for the Preparation of Photoluminescent Polymeric Materials
  作者：José L. Segura、Nazario Martín、Michael Hanack

  DOI：10.1002/(sici)1099-0690(199903)1999:3<643::aid-ejoc643>3.0.co;2-v

  日期：1999.3

  Knoevenagel and Wittig condensation reactions new fluorescent, differently functionalized oligo(2,6-naphthylenevinylene)s have been synthesized, the presence of terminal aldehyde or bromine substitution opening the way to the incorporation of the fluorescent trimers in a variety of polymeric materials. The effect of substituting the phenylene ring by the more bulky dialkoxynaphthalene system in arylenevinylene-type

  提出了适当的萘环对称和不对称官能化的合成策略。通过 Knoevenagel 和 Wittig 缩合反应，合成了新的荧光、不同功能化的低聚（2,6-亚萘基亚乙烯基），末端醛或溴取代的存在为将荧光三聚体掺入各种聚合物材料开辟了道路. 从结构的角度研究了在亚芳基亚乙烯基型材料中用体积更大的二烷氧基萘体系取代亚苯基环的效果，以及通过引入亚萘基亚乙烯基和氰基取代的亚萘基亚乙烯基单元来调节发射颜色和电子亲和力的可能性。也进行了调查。
• Synthesis and Characterization of Novel Optically Active Polyarylene Vinylenes with Controlled Effective Conjugation Length
  作者：Rafael Gómez、José L. Segura、Nazario Martín

  DOI：10.1021/jo000761k

  日期：2000.11.1

  New chiral and soluble binaphthyl derivatives (12 and 13) endowed with carboxaldehyde or cyanomethyl functional groups have been prepared as suitable building blocks for the synthesis by Knoevenagel condensation of a series of optically active block copolymers (1-7) with controlled effective conjugation length. A variety of functionalized co-monomers (14-19) have been prepared by different synthetic procedures to be used in further polymerization reactions with binaphthyl derivatives 12 and 13. Depending upon the nature of the co-monomers, it is possible to tune the wavelength of the new polymers, which is very close to that of the respective repeating units. Fluorescence measurements on polymers 1-3 reveal a strong blue-green emission with Stokes shifts of 74-107 nm. Theoretical calculations at the semiempirical AM-1 level have been carried out on model compounds, and the calculated torsion angles are in agreement with the electronic spectra data. Finally, the redox properties of the polymers prepared (1-7) were determined by cyclic voltammetry, and an amphoteric behavior with oxidation potentials ranging from 1.1 to 1.6 V and reduction potentials close to -1.5 V was found.