Macrocycle Size Matters: “Small” Functionalized Rotaxanes in Excellent Yield Using the CuAAC Active Template Approach

By shrinking the macrocycle in the CuAAC active template reaction not only is it demonstrated to be possible to use smaller macrocycles, but, surprisingly, that smaller macrocycles lead to higher yields of rotaxane product (see scheme). The synthesis of “small” functionalized [2]rotaxanes showcases this as a method for the production of materials with potential applications in molecular electronics, drug delivery, sensing, and enantioselective catalysis.