物理化学学报 >> 2007, Vol. 23 >> Issue (12): 1869-1874.doi: 10.3866/PKU.WHXB20071208

研究论文 上一篇    下一篇

手性双二茂铁基配体的合成、表征及固体CD光谱

黄小青; 宣为民; 陈雷;奇; 章慧; 高景星   

  1. 厦门大学化学化工学院化学系, 固体表面物理化学国家重点实验室, 福建 厦门 361005
  • 收稿日期:2007-08-06 修回日期:2007-09-03 发布日期:2007-11-30
  • 通讯作者: 章慧 E-mail:huizhang@xmu.edu.cn

Synthesis, Characterization and Solid-State CD Spectra of the Chiral Bisferrocenyl Ligands

HUANG Xiao-Qing; XUAN Wei-Min; CHEN Lei-Qi; ZHANG Hui; GAO Jing-Xing   

  1. State Key Laboratory for Physical Chemistry of Solid Surface, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, P. R. China
  • Received:2007-08-06 Revised:2007-09-03 Published:2007-11-30
  • Contact: ZHANG Hui E-mail:huizhang@xmu.edu.cn

摘要: 以甲酰基二茂铁(1)和手性1,2-二苯基乙二胺[(1R, 2R)-1,2-二苯基乙二胺(2R), (1S,2S)-1,2-二苯基乙二胺(2S)]为原料, 经缩合、还原和N-烷基化反应, 制备了一对新型手性四齿双二茂铁基配体[N,N’-二(二茂铁基甲基)-N,N’-二(2-羟基丙基)-(1R,2R)-1,2-二苯基乙二胺(5R)和N,N’-二(二茂铁基甲基)-N,N’-二(2-羟基丙基)-(1S,2S)-1,2-二苯基乙二胺(5S)]. 用元素分析、红外(IR)、质子核磁共振(1H NMR)、紫外-可见(UV-Vis)、固体圆二色(CD)光谱等对手性产物(3R-5S)进行了表征. 固体CD光谱研究表明, 配体5R(或5S)的手性特征和4R(或4S)相似而与3R(或3S)却有一定差别.

关键词: 合成, 手性, 双二茂铁基配体, 固体CD光谱

Abstract: A pair of novel chiral tetradentate bisferrocenyl ligands [N,N’-bisferrocenylmethyl-N,N’-bis (2-hydroproxypyl)-(1R,2R)-1,2-diphenylethane-diamine(5R), N,N’-bisferrocenylmethyl-N,N’-bis(2-hydroxypropyl)-(1S,2S)-1,2-diphenylethane diamine (5S)] were synthesized fromferrocenylcarboxaldehyde (1) and chiral 1,2-diphenylethane-diamine (2R or 2S) followed by the reduction of the Schiff bases with NaBH4 and subsequent N-alkylation with 1,2-propyleneoxide. All the chiral products (3R-5S) were charactered by elemental analysis, infrared (IR), 1H nuclear magnetic resonance (1H NMR), ultraviolet-visible (UV-Vis) and solid-state circular dichroism (CD) spectra. The solid-state CDspectra reveal that the chiral characteristics of 5R (or 5S) are quite similar with 4R (or 4S) and it is also notable that there are some differences between 5R (or 5S) and 3R (or 3S).

Key words: Synthesis, Chirality, Bisferrocenyl ligand, Solid-state circular dichroismspectroscopy

MSC2000: 

  • O641.4