198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

Hydrogen-Bonded Ribbons, Tapes and Sheets as
Motifs for Crystal Engineering
Rosa E. Meléndez · Andrew D. Hamilton
Department of Chemistry, Yale University, New Haven CT 06520–8107, USA.
E-mail: ahamilton@ursula.yale.chem.edu
The design of new architectures for the purpose of crystal engineering has generated great
interest in recent years. In particular, organic compounds have been the focus of many studies
due to the presence of functional groups that can form strong and stable intermolecular interactions.
Therefore, recognizing geometry and functionality at the molecular level has relevant
implications in the design of supramolecular patterns. These patterns in turn can be translated
to physical or chemical properties in a solid. This article is a presentation of compounds
that have been designed for the purpose of molecular recognition and crystal engineering. In
particular our focus will be directed towards organic structures based on the tape, ribbon, and
sheet motifs. Several approaches in the design of functional solids will be presented, emphasizing
the use of certain complementary intermolecular interactions for this purpose. It is not
our attempt to define all concepts used for crystal engineering, but to present recent advances
in this field.
Keywords: Crystal engineering, Molecular recognition, Hydrogen bonding, Tapes, Sheets.
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97
2 Crystal Engineering and Molecular Recognition . . . . . . . . . . . 98
2.1 Strategies for Crystal Engineering . . . . . . . . . . . . . . . . . . . . 99
2.2 Patterns in Crystal Engineering: Tapes, Ribbons, and Sheets . . . . . 100
3 Hydrogen Bonding . . . . . . . . . . . . . . . . . . . . . . . . . . . . 102
3.1 Carboxylic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105
3.2 Amides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 112
3.3 Other Strong Hydrogen Bonds . . . . . . . . . . . . . . . . . . . . . . 120
3.4 Weak Interactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 122
4 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127
5 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127
1
Introduction
Traditional synthetic chemistry is based upon the controlled formation and
cleavage of covalent bonds. However, complicated nanoscale systems would be
extremely difficult to synthesize using traditional covalent methods. As a result,
Topics in Current Chemistry, Vol. 198
© Springer Verlag Berlin Heidelberg 1998