Donor-acceptor interactions between cyclic trinuclear pyridinate gold(i)-complexes and electron-poor guests: nature and energetics of guest-binding and templating on graphite

Chemical Science
Raiko HahnBirgit Esser

Abstract

Donor-acceptor-type interactions between π-electron systems are of high relevance in the design of chemical sensors. Due to their electron-rich nature, cyclic trinuclear complexes (CTCs) of gold(i) are ideal receptor sites for electron-deficient aromatic analytes. Scanning tunneling microscopy provided insight into the structures of two-dimensional crystals of pyridinate gold CTCs that form on a graphite template at the solid/liquid interface. One polymorph thereof - in turn - templated the on-top co-adsorption of π-acidic pyrazolate CTCs as electron-poor guests up to a certain threshold. From NMR titration experiments, we quantified free energies of -6.1 to -7.5 kcal mol-1 for the binding between pyridinate gold(i) CTCs and π-acidic pyrazolate CTCs. Quantum chemical calculations revealed that these interactions are largely dominated by London dispersion. These results give a more detailed insight into a rational design of sensitive CNT- or graphene-based sensors for π-acidic analytes, such as electron-deficient aromatics.

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Citations

Aug 25, 2019·Nature Communications·Shinya AdachiNaoya Kumagai
Sep 8, 2020·Chemistry : a European Journal·G Henrieke HeidemanBen L Feringa
Feb 18, 2021·Angewandte Chemie·Mathias HermannBirgit Esser
Mar 18, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Isaac F LeachJohannes E M N Klein
Nov 28, 2018·Journal of the American Chemical Society·Raiko HahnBirgit Esser

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Methods Mentioned

BETA
X-ray
NMR
1
H

Software Mentioned

RS
COSMO

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