Dynamic Combinatorial Libraries Based on Hydrogen-Bonded Molecular Boxes

✍ Scribed by Jessica M. C. A. Kerckhoffs; Miguel A. Mateos-Timoneda; David N. Reinhoudt; Mercedes Crego-Calama

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 423 KB
• Volume: 13
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200601198

✦ Synopsis

Abstract

This article describes two different types of dynamic combinatorial libraries of host and guest molecules. The first part of this article describes the encapsulation of alizarin trimer 2 a~3~ by dynamic mixtures of up to twenty different self‐assembled molecular receptors together with the amplification and selection of the best binder. Receptors (1 a–d)~3~⋅(DEB)~6~ are formed by the self‐assembly of six diethyl barbiturate (DEB) and calix[4]arene dimelamine derivatives 1 a–d by using hydrogen bonds. The largest amplification factor (2.8) for a host assembly (1 a~3~⋅ (DEB)~6~) was observed after the addition of 2 a to four‐component library 1 a~n~⋅1 b~(3−n)~⋅(DEB)~6~ (n=0–3). Addition of 2 a to twenty‐component library 1 a~n~⋅1 b~m~⋅1 c~o~⋅1 d~(3−(n+m+o))~⋅(DEB)~6~ (n, m, o=0–3; (n+m+o)≤3) also showed amplification of receptor 1 a~3~⋅(DEB)~6~. The second part of this article describes the complexation of libraries of different alizarin‐like guest molecules (2 a–d) and the self‐assembled receptor 1 a~3~⋅(DEB)~6~. This receptor is able to template the formation of the best‐fitting guest trimer.