2,6-bis[2-(5-formyl-2-thienyl)vinyl]-1,5-bis(hexyloxy)naphthalene | 422322-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-bis[2-(5-formyl-2-thienyl)vinyl]-1,5-bis(hexyloxy)naphthalene
• 英文别名: 5-[(E)-2-[6-[(E)-2-(5-formylthiophen-2-yl)ethenyl]-1,5-dihexoxynaphthalen-2-yl]ethenyl]thiophene-2-carbaldehyde
• CAS: 422322-19-8
• 化学式: C₃₆H₄₀O₄S₂
• 分子量: 600.843
• InChiKey: OJBCSVOTGJUOAM-JOBJLJCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-dodecyloxy-6-formylnaphthalene 、 2,6-bis[2-(5-formyl-2-thienyl)vinyl]-1,5-bis(hexyloxy)naphthalene 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95%的产率得到
  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：

  5-溴噻吩-2-甲醛 在 sodium ethanolate 、 二异丁基氢化铝 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 2,6-bis[2-(5-formyl-2-thienyl)vinyl]-1,5-bis(hexyloxy)naphthalene
  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

文献信息

• 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.