Microporous Organic Materials from Hydrophobic Dipeptides

• Published in: Chemistry : a European journal 2007-01, Vol.13 (4), p.1022-1031
• Main Author: Görbitz, Carl Henrik
• Format: Article
• Language: English
• Subjects: dipeptides; Dipeptides - chemistry; hydrogen bonds; Hydrophobic and Hydrophilic Interactions; microporous materials; Models, Molecular; Porosity; Protein Conformation; self-assembly; supramolecular chemistry
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200601427

In the last few years dipeptides with two hydrophobic residues (hydrophobic dipeptides) have emerged as an unexpected source of stable microporous organic materials. Supramolecular self‐assembly of the rather small building blocks is dictated by stringent demands on the hydrogen‐bond formation by the peptide main chains and the aggregation of hydrophobic entities in the side chains. A systematic survey of structures derived from single‐crystal X‐ray diffraction studies has revealed the existence of two large classes of structures, differing in the dimensionality of the hydrogen‐bonding patterns in the crystals and the nature of the channels. The present review summarizes the structural properties of the microporous dipeptides and discusses their potential applications. A new source of stable nanoporous organic materials (an example of which is shown here) is provided by dipeptides with two hydrophobic residues (hydrophobic dipeptides). Based on their crystal structures, these materials can be divided into two classes of structures differing in the dimensionality of the hydrogen‐bonding patterns and in the nature of the channels, which may have hydrophilic or hydrophobic inner surfaces.