methyl 2-(tert-butoxycarbonylamino)-6-(4-(5'''''-methyl-3',3'',3''',3'''',3''''-pentahexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate | 1309383-32-1

• 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-(5'''''-methyl-3',3'',3''',3'''',3''''-pentahexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate
• 英文别名: methyl (2S)-6-[4-[5-[3-hexyl-5-[3-hexyl-5-[3-hexyl-5-[3-hexyl-5-(3-hexyl-5-methylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]triazol-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 1309383-32-1
• 化学式: C₆₉H₉₈N₄O₄S₆
• 分子量: 1239.96
• InChiKey: JTQMIPMVVNYNBT-XSMLMOGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.8
• 重原子数：
  83
• 可旋转键数：
  41
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  265
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2-(tert-butoxycarbonylamino)-6-(4-(5'''''-methyl-3',3'',3''',3'''',3''''-pentahexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.5h， 以92%的产率得到2-(tert-butoxycarbonylamino)-6-(4-(5'''''-methyl-3',3'',3''',3'''',3''''-pentahexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophen-5-yl)-1H-1,2,3-triazol-1-yl)hexanoic acid
  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：

  3-己基-2-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)噻吩 在 N-溴代丁二酰亚胺(NBS) 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 正丁基锂 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 caesium carbonate 、 溶剂黄146 、 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 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 正丁醇 为溶剂， 反应 69.0h， 生成 methyl 2-(tert-butoxycarbonylamino)-6-(4-(5'''''-methyl-3',3'',3''',3'''',3''''-pentahexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophen-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

文献信息

• Hierarchical Self-Assembly of Semiconductor Functionalized Peptide α-Helices and Optoelectronic Properties
  作者：Rohan J. Kumar、James M. MacDonald、Th. Birendra Singh、Lynne J. Waddington、Andrew B. Holmes

  DOI：10.1021/ja110858k

  日期：2011.6.8

  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.