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Tetra‑(meta-butylcarbamoyl)azobenzene: A Rationally Designed Photoswitch with Binding Affinity for Oxoanions in a Long-Lived Z‑State

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journal contribution
posted on 27.02.2017, 16:19 by Kajetan Dąbrowa, Janusz Jurczak
A new photoswitchable anion receptor 1 based on a tetra-meta-substituted azobenzene skeleton has been readily synthesized in two steps. Titration studies (1H NMR) and theoretical predictions (DFT/­M06-2X/­6-31G­(d)/­DMSO-SM8) revealed that nonplanar Z-1 is a better host for anions than E-1, which results from the greater ability of four amide NH protons in the Z-state to cooperatively bind oxoanions, in particular tetrahedral H2PO4 and H2AsO4. Furthermore, the thermal decay of Z-11/2 = 11 days) is not accelerated by anion binding.