methyl 2-(tert-butoxycarbonylamino)-6-(4-(3',3''-dihexyl-2,2':5',2''-terthiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate | 1309383-43-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(tert-butoxycarbonylamino)-6-(4-(3',3''-dihexyl-2,2':5',2''-terthiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate
• CAS: 1309383-43-4
• 化学式: C₃₈H₅₄N₄O₄S₃
• 分子量: 727.069
• InChiKey: CQRXXUZTOUJGFH-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.95
• 重原子数：
  49.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  95.34
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(tert-butoxycarbonylamino)-6-(4-(3',3''-dihexyl-2,2':5',2''-terthiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate 在 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以86%的产率得到methyl 2-(tert-butoxycarbonylamino)-6-(4-(5''-iodo-3',3''-dihexyl-2,2':5',2''-terthiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate
  参考文献：
  名称：

  Hierarchical Self-Assembly of Semiconductor Functionalized Peptide α-Helices and Optoelectronic Properties

  摘要：

  To determine the ability of semiconductors templated by alpha-helical polypeptides to form higher order structures and the charge carrier properties of the supramolecular assemblies, L-lysine was functionalized with a sexithiophene organic semiconductor unit via iterative Suzuki coupling and the click reaction. The resultant amino acid was incorporated into a homopolypeptide by ring-opening polymerization of an amino acid N-carboxyanhydride. Spectroscopic investigation of the polypeptide revealed that it adopted an alpha-helical secondary structure in organic solvents that underwent hierarchical self-assembly to form higher order structures. In cyclohexane, the polymer formed organogels at 2% (w/v). Organic photovoltaic and organic field effect transistor devices were fabricated by deposition of the PCBM blended active layer from chlorobenzene at concentrations shown to induce self-assembly of the polymer. Compared with control compounds, these devices showed significantly greater hole mobility, short circuit current, and efficiency. This work establishes the potential of this previously unreported bioinspired motif to increase device performance.

  DOI：

  10.1021/ja110858k
• 作为产物：
  描述：

  5’-bromo-3’-hexyl-[2,2’-bithiophene]-5-carbaldehyde 在 四(三苯基膦)钯 、 正丁基锂 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 37.0h， 生成 methyl 2-(tert-butoxycarbonylamino)-6-(4-(3',3''-dihexyl-2,2':5',2''-terthiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate
  参考文献：
  名称：

  Hierarchical Self-Assembly of Semiconductor Functionalized Peptide α-Helices and Optoelectronic Properties

  摘要：

  To determine the ability of semiconductors templated by alpha-helical polypeptides to form higher order structures and the charge carrier properties of the supramolecular assemblies, L-lysine was functionalized with a sexithiophene organic semiconductor unit via iterative Suzuki coupling and the click reaction. The resultant amino acid was incorporated into a homopolypeptide by ring-opening polymerization of an amino acid N-carboxyanhydride. Spectroscopic investigation of the polypeptide revealed that it adopted an alpha-helical secondary structure in organic solvents that underwent hierarchical self-assembly to form higher order structures. In cyclohexane, the polymer formed organogels at 2% (w/v). Organic photovoltaic and organic field effect transistor devices were fabricated by deposition of the PCBM blended active layer from chlorobenzene at concentrations shown to induce self-assembly of the polymer. Compared with control compounds, these devices showed significantly greater hole mobility, short circuit current, and efficiency. This work establishes the potential of this previously unreported bioinspired motif to increase device performance.

  DOI：

  10.1021/ja110858k