Covalent template-assisted synthesis of mechanically interlocked molecules

This thesis investigates multiple strategies towards mechanically interlocked compounds using covalent bonds for pre-organization of the components. A small organic template molecule with orthogonal reactivity’s is used for assembly. These templates were designed to covalently bind the ring- and thread fragments and position (constrain) these in a correct way for cyclizations. Depending on the approach, the scaffold was designed to be either removed completely (Chapters II and III) or incorporated in the final product (Chapters IV, V and VI). Chapter I gives a historic and general overview regarding synthetic strategies towards rotaxanes and catenanes. Chapter II investigates the first step in a stepwise strategy towards a rotaxane using a covalent template for pre-organization. Chapter III investigates the subsequent steps towards a [2]rotaxane employing all necessary components and using a oxime bond between ring and thread fragments. Chapter IV describes the synthesis of an unprecedented quasi[1]catenane and quasi[1]rotaxane using a fluorene core for pre-organization. Chapter V continues the work of Chapter III, but using a cyclic ketal between the ring and thread fragments. Chapter VI investigates an entirely different approach towards a [2]rotaxane by using a terephthalic acid template for pre-organization of a ring precursor. Chapter VII describes outlook for this thesis.