Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
J Org Chem. 2012 Sep 7;77(17):7428-34. doi: 10.1021/jo301223q. Epub 2012 Aug 17.
A strategy for the construction of crystalline molecular rotors involves the assemblage of chemical structures that emulate the elements of macroscopic rotary devices, such as those found in macroscopic gyroscopes and compasses. In this report, we describe an efficient and short synthetic route for preparation of molecular rotors with two pentiptycene-units linked at their central benzene ring by triple bonds to a linearly conjugated phenylene rotator. Five analogous compounds with phenol, alkoxy, or alkoxycarbonyl substituents were synthesized and fully characterized in solution and in the solid-state through various methods, such as cross-polarization magic angle spinning (CPMAS) (13)C NMR and single crystal X-ray diffraction. Molecular and packing structures obtained from single crystal X-ray diffraction and crystallization properties were analyzed with the goal of identifying the key parameters that may hinder or facilitate the formation of dynamically functional, crystalline molecular rotors.
一种构建结晶分子转子的策略涉及组装模拟宏观旋转装置（如宏观陀螺仪和指南针中的装置）的化学结构。在本报告中，我们描述了一种有效且简短的合成路线，用于制备通过三键将两个五并苯单元连接在其中心苯环上的分子转子，并连接到线性共轭亚苯基转子上。合成了五个具有苯酚、烷氧基或烷氧羰基取代基的类似物，并通过各种方法（如交叉极化魔角旋转（CPMAS）（13）C NMR 和单晶 X 射线衍射）在溶液中和固态中进行了充分表征。通过单晶 X 射线衍射获得的分子和堆积结构以及结晶性质进行了分析，目的是确定可能阻碍或促进动态功能结晶分子转子形成的关键参数。
