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基于联萘衍生物手性构型高度稳定以及联萘结构中2个萘平面的两面角可以在一定范围内张合的特点,分别以光学活性的(R)和(S)-2,2’-二乙炔基-1,1’-联萘为模板,设计了一种含有8个“铰链”结构单元的新的环芳分子——(R,R,R,R,R,R,R,R)-3和(S,S,S,S,S,S,S,S)-3.其合成路线涉及间苯基连接桥的链接,保护基的脱去和控制导入以及分子间偶合等步骤.用MS,IR,UV-Vis,1H和13CNMR以及元素分析等技术对中间体和目标化合物进行了结构表征.测定并比较了2个目标化合物的比旋光度[α]D和圆二色(CD)性质.在CH2Cl2溶液中,两个异构体(R,R,R,R,R,R,R,R)-3和(S,S,S,S,S,S,S,S)-3的[α]2D5值分别为-911.8和+908.6,并且它们的CD谱表现出对称的镜像特征.这些实验结果清楚地反映了它们之间的对映异构关系.
Based on the highly stable chiral configuration of the binaphthyl derivatives and the fact that the dihedral angles of two naphthalene planes in the binaphthyl structure can be expanded in a certain range, the optically active (R) and (S) -2,2 ’ -diacetylene-1,1’-binaphthyl was used as a template to design a novel ring aromatic molecule with 8 “hinge” structural units - (R, R, R, R, R, R, (S, S, S, S, S, S, S) -3. The synthetic route involves the linkages of the m-phenyl linkages, the deprotection and control of the protecting groups, the intermolecular coupling, and the like The intermediate and target compounds were characterized by means of MS, IR, UV-Vis, 1H and 13CNMR as well as elemental analysis.The specific rotation [α] D and circular dichroism of two target compounds were determined and compared, (CD), the two isomers (R, R, R, R, R, R, R, R) -3 and (S, S, S, S, S, S, S, S] -3 has [α] 2D5 values of -911.8 and +908.6, respectively, and their CD spectra exhibit symmetrical mirror images.These experimental results clearly show the enantiomeric relationship between them.