A Modular Approach to Introduce Function into Single‐Chain Polymeric Nanoparticles. Issue 15 (25th June 2014)

• Record Type: Journal Article
• Authors: Huerta, Elisa; van Genabeek, Bas; Stals, Patrick J. M.; Meijer, E. W.; Palmans, Anja R. A.
• Is Part Of: Macromolecular rapid communications. Volume 35:Issue 15(2014:Aug.)
• Page Start: 1320
• Page End: 1325
• Publication Date: 2014-06-25
• Subjects: Macromolecules -- Periodicals; Polymers -- Periodicals; Chemistry -- Periodicals; 547.705
• DOI: 10.1002/marc.201400213
• Languages: English
• ISSNs: 1022-1336

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>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 <italic><sc>l</sc></italic>‐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, <italic><sc>l</sc></italic>‐proline‐based BTAs are incorporated to procure a catalytically active SCPN in water. The aldol reaction between <italic>p</italic>‐nitrobenzaldehyde and cyclohexanone shows good conversions at low catalyst loadings and substrate concentrations, and high stereoselectivities are obtained (<italic>de</italic> = 91% and <italic>ee</italic> = 98%). <boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pghxn0ntfn" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>