Zhu Kelong, Baggi Giorgio, Vukotic V Nicholas, Loeb Stephen J
School of Chemistry , Sun Yat-Sen University , Guangzhou , 510275 , P. R. China . Email:
Department of Chemistry and Biochemistry , University of Windsor , Windsor , Ontario N9B 3P4 , Canada . Email:
Chem Sci. 2017 May 1;8(5):3898-3904. doi: 10.1039/c7sc00790f. Epub 2017 Mar 28.
The T-shaped benzimidazolium/crown ether recognition motif was used to prepare suit[1]anes. These novel mechanically interlocked molecules (MIMs) were fully characterized by H and C NMR spectroscopy, single-crystal X-ray diffraction, UV-vis absorption and fluorescence spectroscopy. By conversion to a suit[1]ane, a simple benzimidazole was shown to be protected from deprotonation by strong base. Moreover, it was demonstrated that this unique three-dimensional encapsulation can be made reversible, thus introducing the concept of "reversible mechanical protection"; a protecting methodology that may have potential applications in synthetic organic chemistry and the design of molecular machinery.
T形苯并咪唑鎓/冠醚识别基序被用于制备索烃[1]烷。这些新型的机械互锁分子（MIMs）通过氢核磁共振和碳核磁共振光谱、单晶X射线衍射、紫外可见吸收光谱和荧光光谱进行了全面表征。通过转化为索烃[1]烷，一种简单的苯并咪唑被证明能免受强碱的去质子化作用。此外，已证明这种独特的三维封装可以是可逆的，从而引入了“可逆机械保护”的概念；一种可能在有机合成化学和分子机器设计中具有潜在应用的保护方法。
