Title: Polyphosphorylated Triphenylenes: Synthesis, Crystal Structure, and Selective Catechol Recognition
Authors: Givelet, Cecile
Tinant, Bernard
Van Meervelt, Luc
Buffeteau, Thierry
Marchand-Geneste, Nathalie
Bibal, Brigitte # ×
Issue Date: Jan-2009
Publisher: Amer chemical soc
Series Title: Journal of Organic Chemistry vol:74 issue:2 pages:652-659
Abstract: Designed as a multivalent hydrogen bond acceptor, new receptors, Discopus 1a,b, were built from a triphenylene core surrounded by six (diaryl)phosphinate groups. An efficient synthesis was developed to prepare these elaborated structures in a high overall yield. The X-ray structure of receptor 1b showed strong cooperative hydrogen bonds with two water molecules and intermolecular CH-pi contacts. In chloroform, Discopus la,b displayed recognition properties toward dihydroxybenzenes, selectively forming complexes with catechol derivatives 4a-c in a 1:2 (host:guest) stoichiometry. According to NMR and microcalorimetry titrations, association constants were found in the 30-2837 M-1 range, which were larger than those reported for curvated catechol receptors (14-120 M-1). Interestingly, Discopus present two distinct catechol binding sites. Weak hydrogen bonding between host phosphinates and guest hydroxyl groups was shown by infrared spectroscopy and P-31 NMR. Molecular dynamics simulations and recognition experiments suggested that a stronger hydrogen bond assisted by a pi-interaction between the Discopus core and one catechol molecule could exist within the :2 complex.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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