title: Supramolecular polymers for organocatalysis in water.
abstract: A water-soluble benzene-1,3,5-tricarboxamide (BTA) derivative that self-assembles into one-dimensional, helical, supramolecular polymers is functionalised at the periphery with one L-proline moiety. In water, the BTA-derivative forms micrometre long supramolecular polymers, which are stabilised by hydrophobic interactions and directional hydrogen bonds. Furthermore, we co-assemble a catalytically inactive, but structurally similar, BTA with the L-proline functionalised BTA to create co-polymers. This allows us to assess how the density of the L-proline units along the supramolecular polymer affects its activity and selectivity. Both the supramolecular polymers and co-polymers show high activity and selectivity as catalysts for the aldol reaction in water when using p-nitrobenzaldehyde and cyclohexanone as the substrates for the aldol reaction. After optimisation of the reaction conditions, a consistent conversion of 92 ± 7%, deanti of 92 ± 3%, and eeanti of 97 ± 1% are obtained with a concentration of L-proline as low as 1 mol%.
authors.affiliation: Laboratory for Macromolecular and Organic Chemistry, Institute for Complex Molecular Sciences, TU Eindhoven, PO Box 513, 5600 MB Eindhoven, The Netherlands. a.palmans@tue.nl e.w.meijer@tue.nl.
authors.forename: Laura N
authors.initials: LN
authors.lastname: Neumann
authors.forename: Matthew B
authors.initials: MB
authors.lastname: Baker
authors.forename: Christianus M A
authors.initials: CM
authors.lastname: Leenders
authors.forename: Ilja K
authors.initials: IK
authors.lastname: Voets
authors.forename: René P M
authors.initials: RP
authors.lastname: Lafleur
authors.forename: Anja R A
authors.initials: AR
authors.lastname: Palmans
authors.forename: E W
authors.initials: EW
authors.lastname: Meijer
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D001549:Benzamides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D046911:Macromolecular Substances / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D001547:Benzaldehydes; D001549:Benzamides; D003512:Cyclohexanones; D046911:Macromolecular Substances; D011108:Polymers; C558700:benzene-1,3,5-tricarboxamide; D014867:Water; C029915:4-nitrobenzaldehyde; C036468:cyclohexanone