4-Amino-1-butyl-5-(5,12-dithiatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),6,8,10,13-heptaen-6-yl)pyrimidin-2-one | 1404458-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 4-Amino-1-butyl-5-(5,12-dithiatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),6,8,10,13-heptaen-6-yl)pyrimidin-2-one
• 英文别名: 4-amino-1-butyl-5-(5,12-dithiatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),6,8,10,13-heptaen-6-yl)pyrimidin-2-one
• CAS: 1404458-22-5
• 化学式: C₂₂H₁₉N₃OS₂
• 分子量: 405.544
• InChiKey: JHPWPVRUCXLSTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,6-dithiapyrene 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 氨 作用下， 以 四氢呋喃 为溶剂， 生成 4-Amino-1-butyl-5-(5,12-dithiatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),6,8,10,13-heptaen-6-yl)pyrimidin-2-one
  参考文献：
  名称：

  Nucleobase-Functionalized 1,6-Dithiapyrene-Type Electron-Donors: Supramolecular Assemblies by Complementary Hydrogen-Bonds and π-Stacks

  摘要：

  Synthesis, crystal structures and redox properties Of 1,6-dithiapyrene (DTPY)-type electron donors functionalized with nucleobases (uracil, cytosine and adenine) were investigated. The electrochemical measurements showed that the uracil-substituted derivatives were slightly stronger electron-donors than DTPY, and the cytosine- and adenine-substitution caused a slight weakening of the electron-donating ability. In the crystal structures, DTPY-nucleobases constructed multidimensional assemblies by complementary hydrogen-bonds on the nucleobase moieties and pi-stacks and S center dot center dot center dot S interactions on the DTPY skeleton. The uracil derivative formed two kinds of hydrogen-bonded pairs with different H-bonding modes (Watson-Crick and reverse Watson-Crick types), both of which were further linked through pi-stacks on the DTPY skeleton to construct one-dimensional alternating columns. In the CH2Cl2 solvated crystal, the uracil derivative built up a two-dimensional pi-layer by the complementary hydrogen bonds and pi-stacks In the cytosine derivative, the complementary hydrogen bonded pair assembled by the pi-stacks and S center dot center dot center dot S interactions of the DTPY skeleton constructed a two-dimensional network The adenine derivative formed a channel structure by the one-dimensional pi-stack of complementary hydrogen-bonded pairs, where crystalline water molecules with a ladder-like hydrogen-bonded chain were included. Charge-transfer complexes of DTPY-nucleobases with tetracyanoquinodimethane possessed a neutral ground state and exhibited semiconductive behaviors with room temperature conductivities of 10(-6) to 10(-7) S cm(-1).

  DOI：

  10.1021/cg301414s

文献信息

• Nucleobase-Functionalized 1,6-Dithiapyrene-Type Electron-Donors: Supramolecular Assemblies by Complementary Hydrogen-Bonds and π-Stacks
  作者：Tsuyoshi Murata、Eigo Miyazaki、Kazuhiro Nakasuji、Yasushi Morita

  DOI：10.1021/cg301414s

  日期：2012.11.7

  Synthesis, crystal structures and redox properties Of 1,6-dithiapyrene (DTPY)-type electron donors functionalized with nucleobases (uracil, cytosine and adenine) were investigated. The electrochemical measurements showed that the uracil-substituted derivatives were slightly stronger electron-donors than DTPY, and the cytosine- and adenine-substitution caused a slight weakening of the electron-donating ability. In the crystal structures, DTPY-nucleobases constructed multidimensional assemblies by complementary hydrogen-bonds on the nucleobase moieties and pi-stacks and S center dot center dot center dot S interactions on the DTPY skeleton. The uracil derivative formed two kinds of hydrogen-bonded pairs with different H-bonding modes (Watson-Crick and reverse Watson-Crick types), both of which were further linked through pi-stacks on the DTPY skeleton to construct one-dimensional alternating columns. In the CH2Cl2 solvated crystal, the uracil derivative built up a two-dimensional pi-layer by the complementary hydrogen bonds and pi-stacks In the cytosine derivative, the complementary hydrogen bonded pair assembled by the pi-stacks and S center dot center dot center dot S interactions of the DTPY skeleton constructed a two-dimensional network The adenine derivative formed a channel structure by the one-dimensional pi-stack of complementary hydrogen-bonded pairs, where crystalline water molecules with a ladder-like hydrogen-bonded chain were included. Charge-transfer complexes of DTPY-nucleobases with tetracyanoquinodimethane possessed a neutral ground state and exhibited semiconductive behaviors with room temperature conductivities of 10(-6) to 10(-7) S cm(-1).