Molecules with interlocked architectures offer valuable structural possibilities for modulating and tuning the properties of the entwined components. Rotaxanes, molecules comprising a irremovable rod–shaped axle threaded through the cavity of an encircling macrocycle, have found application as a means to both enhance a desired material property of a central component and diminish the possibility of unwanted reactivity. For example, a class of important organic dye exhibits both enhanced optical properties and diminished reactivity toward nucleophiles once enclosed in a rotaxane architecture. Efficient preparation of these mechanically interlocked structures requires strong binding of the guest thread to the host macrocycle. Both kinetically and thermodynamically controlled reactions may subsequently be employed to append the sterically bulky end groups required to prevent escape of the threaded component. Against this background solid state chemistry holds considerable appeal as binding of complementary components may be maximized. As an extension to prior investigation of solution reactions of aldehydes with various carbon nucleophiles description of efforts directed toward the deployment of these and related reactions in the solid state will be described. The further development of elements of this work for use in the undergraduate teaching laboratory will also be presented.

Approaches to molecular interlocking in the solid state

253rd National Meeting (2017)

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