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Polyglycerol‐Tagged Molecular Clips as Receptors in Protic Solvents
Author(s) -
Zieringer Maximilian,
Casas Cartagena Marçal,
Burakowska Ewelina,
Taktikos Johannes,
Neuthe Katja,
Bandmann Heinz,
Klärner FrankGerrit,
Haag Rainer
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200345
Subject(s) - chemistry , supramolecular chemistry , molecular tweezers , substituent , iodide , titration , dendrimer , molecule , methanol , proton nmr , methyl iodide , molecular recognition , salt (chemistry) , gibbs free energy , combinatorial chemistry , polymer chemistry , stereochemistry , organic chemistry , physics , quantum mechanics
Four charge‐neutral molecular clips modified with polyglycerol (PG) dendrons of first and second generation and with hyperbranched polyglycerols (HPG) in the central unit as solubilizing units were synthesized. Their use as supramolecular hosts for the complexation of several guest molecules such as caffeine, N ‐methylnicotinamide iodide, and Kosower salt was studied in methanol and water. Association constants and Gibbs enthalpies of association were determined by 1 H NMR titration experiments. The obtained results were compared to the association behavior of molecular clips that carry anionic substituents. These results offer remarkable insights into the contribution of the substituents to host–guest binding and enable a strategy for improved substituent design.