title: A modular approach to introduce function into single-chain polymeric nanoparticles.
abstract: Here, a modular approach is reported to introduce a specific function into single-chain polymeric nanoparticles (SCPNs). Hereto, an amphiphilic polymer with pendant benzene-1,3,5-tricarboxamide (BTA) units is mixed with a "free" BTA that contains a functional group, either a fluorescent naphthalimide or a catalytically active l-proline. Taking advantage of hydrophobic interactions and self-recognition properties of the BTA units, the "free" BTAs are captured into the interior of the SCPN in water as evidenced by fluorescence studies. To illustrate that function can be readily introduced using a modular approach, l-proline-based BTAs are incorporated to procure a catalytically active SCPN in water. The aldol reaction between p-nitrobenzaldehyde and cyclohexanone shows good conversions at low catalyst loadings and substrate concentrations, and high stereoselectivities are obtained (de = 91% and ee = 98%).
authors: Laboratory of Macromolecular and Organic Chemistry, Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600, MB, Eindhoven, The Netherlands.
authors: Elisa
authors: E
authors: Huerta
authors: Bas
authors: B
authors: van Genabeek
authors: Patrick J M
authors: PJ
authors: Stals
authors: E W
authors: EW
authors: Meijer
authors: Anja R A
authors: AR
authors: Palmans
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001549:Benzamides / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D053758:Nanoparticles / Q000737:chemistry*; D053644:Naphthalimides / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001549:Benzamides; D003512:Cyclohexanones; D053644:Naphthalimides; D011108:Polymers; C558700:benzene-1,3,5-tricarboxamide; D014867:Water; C036468:cyclohexanone; C116609:3-hydroxybutanal; D011392:Proline
keywords: aldol reaction; benzene-1,3,5-tricaboxamide; molecular recognition; organocatalysis; single-chain polymeric nanoparticles