N,N-diphenyl-N-(naphtho[2.1-b]thieno[2,3-b:3',2'-d]dithiophen-5-yl)amine | 1610617-74-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-diphenyl-N-(naphtho[2.1-b]thieno[2,3-b:3',2'-d]dithiophen-5-yl)amine
• 英文别名: N,N-diphenyl-6,8,10-trithiapentacyclo[9.8.0.02,9.03,7.014,19]nonadeca-1(11),2(9),3(7),4,12,14(19),15,17-octaen-17-amine
• CAS: 1610617-74-7
• 化学式: C₂₈H₁₇NS₃
• 分子量: 463.648
• InChiKey: KLCZYGBJOFBTDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三苯胺 在 sodium tetrahydroborate 、 potassium tert-butylate 、 碘 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 58.0h， 生成 N,N-diphenyl-N-(naphtho[2.1-b]thieno[2,3-b:3',2'-d]dithiophen-5-yl)amine
  参考文献：
  名称：

  From N,N-diphenyl-N-naphtho[2,1-b]thieno[2,3-b:3′,2′-d]dithiophene-5-yl-amine to propeller-shaped N,N,N-tri(naphtho[2,1-b]thieno[2,3-b:3′,2′-d]dithiophene-5-yl)-amine: syntheses and structures

  摘要：

  Three unique propeller-shaped helicenyl amines compounds: N,N-diphenyl-N-naphtho[2,1-b]thieno[2,3b:3 ',2 '-c]Iclithiophene-5-yl-amine (1), N-phenyl-N,N-di(naphtho[2,1-b]thieno[2,3-6:3 ',2 '-d]dithiophene5-yl)amine (2), and N,N,N-tri(naphtho[2,1-b]thieno[2,3-b:3 ',2 '-d]dithiophene-5-yl)amine (3) were efficiently synthesized by Wittig reaction and oxidative photocyclization. The crystal structures of 1, 2 and molecular configuration optimization (DFT-B3LYP/6-3 +G(d)) of 3 reveal that the steric hindrance from the moiety of trithia[5]helicene effectively forces the nitrogen atom and the three bonded carbon atoms to coplanar and the interplanar angles of the facing terminal thiophene ring and benzene ring becoming larger when the helical arm increased from 1 to 3. Electrochemical properties and UV-vis absorption behaviors of 1, 2, 3 were primarily determined by the moiety of trithia[5]helicene. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.031

文献信息

• From N,N-diphenyl-N-naphtho[2,1-b]thieno[2,3-b:3′,2′-d]dithiophene-5-yl-amine to propeller-shaped N,N,N-tri(naphtho[2,1-b]thieno[2,3-b:3′,2′-d]dithiophene-5-yl)-amine: syntheses and structures
  作者：Chunli Li、Yongqing Zhang、Sheng Zhang、Jianwu Shi、Yuhe Kan、Hua Wang

  DOI：10.1016/j.tet.2014.04.031

  日期：2014.6

  Three unique propeller-shaped helicenyl amines compounds: N,N-diphenyl-N-naphtho[2,1-b]thieno[2,3b:3 ',2 '-c]Iclithiophene-5-yl-amine (1), N-phenyl-N,N-di(naphtho[2,1-b]thieno[2,3-6:3 ',2 '-d]dithiophene5-yl)amine (2), and N,N,N-tri(naphtho[2,1-b]thieno[2,3-b:3 ',2 '-d]dithiophene-5-yl)amine (3) were efficiently synthesized by Wittig reaction and oxidative photocyclization. The crystal structures of 1, 2 and molecular configuration optimization (DFT-B3LYP/6-3 +G(d)) of 3 reveal that the steric hindrance from the moiety of trithia[5]helicene effectively forces the nitrogen atom and the three bonded carbon atoms to coplanar and the interplanar angles of the facing terminal thiophene ring and benzene ring becoming larger when the helical arm increased from 1 to 3. Electrochemical properties and UV-vis absorption behaviors of 1, 2, 3 were primarily determined by the moiety of trithia[5]helicene. (C) 2014 Elsevier Ltd. All rights reserved.