We report here the first phase in the rational design of a versatile hydrogen-bonded supramolecular 'zipper', by creating a molecular 'tool box'. These are novel structures that are predicted to undergo self-assembled and to form stable 'zippers', which should be amendable to molecular manipulations that change the physical properties of the supramolecule, while preserving the three-dimensional structure. We emphasize design rationale, including examples, and also demonstrate the importance of using highly accurate computational methods in molecular design. (C) 2004 Elsevier B.V. All rights reserved.