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Multi-State Regulation of the Dihydrogen Phosphate Binding Affinity to a Light- and Heat-Responsive Bis-Urea Receptor

A responsive bis-urea receptor can be switched between three isomers using light and heat as evidenced by 1H NMR and UV–vis spectroscopy. Anion binding experiments (1H NMR titrations, ESI-MS) reveal a high selectivity for dihydrogen phosphate. Importantly, a large difference in binding affinity to t...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-12, Vol.136 (48), p.16784-16787
Main Authors: Wezenberg, Sander J, Vlatković, Matea, Kistemaker, Jos C. M, Feringa, Ben L
Format: Article
Language:English
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Summary:A responsive bis-urea receptor can be switched between three isomers using light and heat as evidenced by 1H NMR and UV–vis spectroscopy. Anion binding experiments (1H NMR titrations, ESI-MS) reveal a high selectivity for dihydrogen phosphate. Importantly, a large difference in binding affinity to the interchangeable isomers is observed, which is further rationalized by DFT calculations. As a consequence, the amount of bound substrate can be controlled via photo- and thermal isomerization in a three-step process.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja510700j