methyl 3-(nonylamino)-5-(2'-(5',2'',5'',2'''-terthienyl))benzoate | 1268704-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: methyl 3-(nonylamino)-5-(2'-(5',2'',5'',2'''-terthienyl))benzoate
• 英文别名: Methyl 3-(nonylamino)-5-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]benzoate
• CAS: 1268704-04-6
• 化学式: C₂₉H₃₃NO₂S₃
• 分子量: 523.785
• InChiKey: SOQCEGSLTTYKSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-(nonylamino)-5-(2'-(5',2'',5'',2'''-terthienyl))benzoate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以13%的产率得到TTC3A
  参考文献：
  名称：

  Self-Assembly of Oligothiophene Chromophores by m-Calix[3]amide Scaffold

  摘要：

  m-Calix[3]amides carrying the bithiophene chromophore (BTC3A) and terthiophene chromophore (TTC3A) were synthesized by the cyclic trimerization of m-aminobenzoic acid esters for the purpose of the control and understanding of the self-assembly of oligothiophene chromophores. Polymers and model compounds were also prepared for comparison. From the (1)H NMR experiments, cyclic trimer BTC3A showed the syn/ anti equilibrium in solution, and the syn/anti conformer ratio (76/24 in CDCl(3)) was influenced by the solvent character. Namely, the population of the syn conformer was lowest (70%) in THF-d(8) and was highest (86%) in CDCl(3)/CD(3)OD (1/1 in volume). On the other hand, the population of the syn conformer of cyclic trimer TTC3A was high (84%) even in CDCl(3). In a CHCl(3) solution of cyclic trimer BTC3A, the absorption maximum (342 nm) blue-shifted and the emission maximum (448 nm) red-shifted compared with those of polymer BTPA and model compound BTM. The solvent character also had an impact on the optical properties of cyclic trimer BTC3A. The red-shifted emission maximum (481 nm) of cyclic trimer BTC3A in CH(3)OH indicated the interaction between three bithiophene chromophores. The emission maxima of cyclic trimer TTC3A (486 nm) demonstrated a small red-shift from model compound TTM (477 nm), and no solvent dependency was observed, unlike cyclic trimer BTC3A.

  DOI：

  10.1021/jo102160x
• 作为产物：
  描述：

  3-氨基-5-溴苯甲酸甲酯 在 四(三苯基膦)钯 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 methyl 3-(nonylamino)-5-(2'-(5',2'',5'',2'''-terthienyl))benzoate
  参考文献：
  名称：

  Self-Assembly of Oligothiophene Chromophores by m-Calix[3]amide Scaffold

  摘要：

  m-Calix[3]amides carrying the bithiophene chromophore (BTC3A) and terthiophene chromophore (TTC3A) were synthesized by the cyclic trimerization of m-aminobenzoic acid esters for the purpose of the control and understanding of the self-assembly of oligothiophene chromophores. Polymers and model compounds were also prepared for comparison. From the (1)H NMR experiments, cyclic trimer BTC3A showed the syn/ anti equilibrium in solution, and the syn/anti conformer ratio (76/24 in CDCl(3)) was influenced by the solvent character. Namely, the population of the syn conformer was lowest (70%) in THF-d(8) and was highest (86%) in CDCl(3)/CD(3)OD (1/1 in volume). On the other hand, the population of the syn conformer of cyclic trimer TTC3A was high (84%) even in CDCl(3). In a CHCl(3) solution of cyclic trimer BTC3A, the absorption maximum (342 nm) blue-shifted and the emission maximum (448 nm) red-shifted compared with those of polymer BTPA and model compound BTM. The solvent character also had an impact on the optical properties of cyclic trimer BTC3A. The red-shifted emission maximum (481 nm) of cyclic trimer BTC3A in CH(3)OH indicated the interaction between three bithiophene chromophores. The emission maxima of cyclic trimer TTC3A (486 nm) demonstrated a small red-shift from model compound TTM (477 nm), and no solvent dependency was observed, unlike cyclic trimer BTC3A.

  DOI：

  10.1021/jo102160x

文献信息

• Self-Assembly of Oligothiophene Chromophores by <i>m</i>-Calix[3]amide Scaffold
  作者：Koji Takagi、Shinri Sugimoto、Ryohei Yamakado、Katsuya Nobuke

  DOI：10.1021/jo102160x

  日期：2011.4.15

  m-Calix[3]amides carrying the bithiophene chromophore (BTC3A) and terthiophene chromophore (TTC3A) were synthesized by the cyclic trimerization of m-aminobenzoic acid esters for the purpose of the control and understanding of the self-assembly of oligothiophene chromophores. Polymers and model compounds were also prepared for comparison. From the (1)H NMR experiments, cyclic trimer BTC3A showed the syn/ anti equilibrium in solution, and the syn/anti conformer ratio (76/24 in CDCl(3)) was influenced by the solvent character. Namely, the population of the syn conformer was lowest (70%) in THF-d(8) and was highest (86%) in CDCl(3)/CD(3)OD (1/1 in volume). On the other hand, the population of the syn conformer of cyclic trimer TTC3A was high (84%) even in CDCl(3). In a CHCl(3) solution of cyclic trimer BTC3A, the absorption maximum (342 nm) blue-shifted and the emission maximum (448 nm) red-shifted compared with those of polymer BTPA and model compound BTM. The solvent character also had an impact on the optical properties of cyclic trimer BTC3A. The red-shifted emission maximum (481 nm) of cyclic trimer BTC3A in CH(3)OH indicated the interaction between three bithiophene chromophores. The emission maxima of cyclic trimer TTC3A (486 nm) demonstrated a small red-shift from model compound TTM (477 nm), and no solvent dependency was observed, unlike cyclic trimer BTC3A.