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In this thesis, Bernhard Schmidt describes his research into two fields in the chemical sciences: supramolecular and macromolecular chemistry. Schmidt first investigates cyclodextrins (CDs), which are well known for the formation of supramolecular host/guest complexes with hydrophobic molecules in aqueous solution. Schmidt then also examines reversible addition-fragmentation chain transfer (RAFT) polymerization as a well-suited toll for the synthesis of water-soluble end-functionalized polymers. The author skillfully combines both concepts as a powerful tool to access reversibly forming macromolecular architectures. The novel methods and architectures presented in this work are highly interesting from both a fundamental point of view as well as a basis for the design of efficient drug release systems. The work in this thesis has led to a number of publications in top peer-reviewed journals.