Various mechanically interlocked moleculaes such as rotaxanes and catenanes have been prepared towards future realization of molecular machines.  It is well-established that a strategy for the synthesis of rotaxanes is mainly interdigitation via p-p stacking, hydrogen bonding, and ion-templated complexation.  However, it would seem to be restrictive that cationic hydrogen-bonded and ion-templated rotaxanes are applied for a molecular sensor and a catalyst.  Herein, we describe the synthesis of of a ditopic macrocycle with a isophthalamide and a half dibenzo-crown ether component and its complexation behavior toward neutral phenanthroline derivatives.   The macrocycle can bind phenanthroline derivatives very strongly by hydrogen bonding and p-p stacking, yielding pseudorotaxane assemblies.  In addition, there is a large variation in binding strength across the macrocycles.  The smaller macrocycle can bind pehanthroline derivatives with a much greater affinity than the larger macrocycle.

Pseudorotaxane assemblies containing phenanthroline threading components without ion template

244th National Meeting (2012)

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