Toyota Shinji, Ikeda Hiroshi, Iwanaga Tetsuo
Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8551, Japan.
Tokyo Metropolitan College of Industrial Technology, 1-10-40 Higashi-Oi, Shinagawa-ku, Tokyo, 140-0011, Japan.
Chempluschem. 2017 Jul;82(7):957-966. doi: 10.1002/cplu.201600646. Epub 2017 Feb 22.
Planar and rigid frameworks that consist of two 1,8-substituted anthracene units and two acetylene linkers were utilized as key structures for the generation of stereoisomers through the introduction of extra substituents. These compounds were synthesized from 1,8-substituted anthracene building units by a combination of coupling reactions. We designed diastereomers, enantiomers, and topomers by modifying the combination of the two linkers and the number of substituents at sterically crowded intraannular positions. The molecular structures, stereochemistry, and properties of these compounds were investigated by means of spectroscopic techniques and theoretical calculations. A prochiral cyclic dimer with one extraannular substituent was designed to generate a stereochemical phenomenon in two dimensions. Scanning tunneling microscopy measurements revealed that the molecules formed a self-assembled monolayer at the liquid-solid interface in a conglomerate-type manner. The scope and potential of the macrocyclic frameworks in studies of π-conjugated compounds are presented.
由两个1,8-取代蒽单元和两个乙炔连接体组成的平面刚性框架被用作通过引入额外取代基来生成立体异构体的关键结构。这些化合物由1,8-取代蒽构建单元通过偶联反应组合合成。我们通过改变两个连接体的组合以及在空间拥挤的环内位置的取代基数来设计非对映异构体、对映异构体和拓扑异构体。通过光谱技术和理论计算研究了这些化合物的分子结构、立体化学和性质。设计了一种带有一个环外取代基的前手性环状二聚体以在二维中产生立体化学现象。扫描隧道显微镜测量表明，分子在液-固界面以聚集体类型的方式形成了自组装单分子层。介绍了大环框架在π共轭化合物研究中的范围和潜力。
