A stable ternary inclusion complex comprising a host, an electron donor, and an electron acceptor with a long alkyl tail (see schematic representation) triggers the spontaneous formation of giant vesicles (see TEM image). The ternary complex behaves as a supramolecular amphiphile with a large polar head group and a single hydrophobic tail. Treatment of the complex with an oxidizing agent results in disruption of the vesicles.
Click reaction of propargyl methacrylate (1) with 6I-azido-6I-deoxycyclomaltoheptaose (2) was carried out to synthesize mono-(1H-1,2,3-triazol-4-yl)(methyl)2-methylacryl-β-cyclodextrin (3). The process was investigated by varying the reaction time, temperature profiles, and copper catalyst. Microwave irradiation was compared with conventional heating. The microwave-assisted Cu(I)-catalyzed cycloaddition affords the complete conversion of (2) into 1,4-disubstituted triazole in a significant decreased reaction time. Under microwave conditions, the cycloaddition of (2) onto poly(propargyl methacrylate) (5) was conducted in excellent yields. The regioselectivity of click reactions in dependence of reaction conditions was evaluated by use of NMR spectroscopy. The reactions performed under microwave conditions led exclusively to 1,4-disubstituted triazole, while the conventional heating led to a regioisomeric mixture.
A fine host: Copolymers from methacrylated β‐cyclodextrin and N‐isopropylacrylamide form inclusion complexes with anions of ionic liquids (IL; see picture). Complex formation alters the solubility properties of the copolymer, leading to pseudopolyelectrolytes. Turbidity and dynamic light scattering measurements show that, depending on the anion, expansion or contraction of the polymer chain takes place owing to electrostatic effects.
We describe the synthesis of a combi-receptor via the click reaction of 6I-azido-6I-deoxycyclomaltoheptaose onto (propargyl-O) 6 cucurbit[6]uril under microwave-assisted conditions. The process was investigated by 1 H NMR, FT-IR spectroscopy, and MALDI-TOF mass spectrometry. The ability of the synthesized compound to act as a molecular receptor and supramolecular building block in combination with NIPAM-and adamantane-containing methacrylates was investigated by turbidity measurement and dynamic light scattering (DLS).
We gratefully acknowledge the Creative Research Initiative Program of the Korean Ministry of Science and Technology for support of this work and the Brain Korea 21 Program of the Korean Ministry of Education for a graduate studentship (Y.J.J.). We thank Drs. Hee-Joon Kim and Young Ho Ko for helpful suggestions and help, respectively, in the NMR study. We also thank Prof. Hee-Tae Jung of KAIST for helpful discussions on the TEM experiments.Supporting information for this article is available on the WWW under http://www.angewandte.org or from the author. Scheme 1. Formation of stable ternary complexes 1, 2, and 3.
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