分别从手性构型高度稳定的(R)和(S)-2,2'-二乙炔基-1,1’-联萘模板出发,通过保护基的控制导入、偶联反应、保护基脱去以及分子间偶合成环4个步骤成功地合成了一种具有螺旋结构特征的新的光学活性分子方(Molecular square)——(R,R,R,R)-1和(S,S,S,S)-1.用MS,IR,UV-Vis,^1H和^13C NMR以及元素分析等方法对目标化合物进行了结构表征.测定并分析比较了2个目标化合物的比旋光度[α]D和圆二色性(CD)等光学性质.在CH2Cl2溶液中,异构体(R,R,R,R)-1和(S,S,S,S)-1的[α]0^25值分别为+887.3°和-889.7°,并且其CD谱表现出对称的镜像特征。
(R)- and(S)-2,2'-diethynyl-1,1 '-binaphthyl with highly stable chiral configurations were used as the structural templates and linking bridges, and a new type of chiral molecular square with helical structure ( R, R, R, R) -1 and ( S, S, S, S) -1 were synthesized in enantiopure form via four steps including the introduction of protecting-group, intermolecular coupling reaction, removal of protecting group, and intermolecular crosscoupling cyclyzation. Compound 1 was characterized by MS, IR, ^1H and ^13C NMR as well as elemental analysis. The specific rotations( [α]D^25) of the two isomers in CH2Cl2 are + 887.3° and -889.7°, respectively, and their circular dichroism(CD) spectra represented exactly the mirror images of each other. These results reflected unambiguously enantiomeric relationship between the two isomers.