Alkylene- and arylene-linked bis(amidines) have attracted considerable attention as building blocks for biomedical reagents, redox-switchable chromophores and fluorophores, and also as versatile ligands in coordination chemistry. Herein, we present a series of new flexible tetra- and hexadentate ethylene-linked bis(amidines) that either show versatile networks of inter- and intramolecular hydrogen bonds or encapsulated N–H groups, as revealed by X-ray crystallography and IR spectroscopy. We also found strong evidence for hydrogen bonding being retained in solution for bis(amidines) that show hydrogen bonds in the solid state. A comprehensive computational study (gas phase and solution) supports these observations. Remarkably, the reported bis(amidines) become substantially emissive in THF solutions upon deprotonation using <i><sup>n</sup></i>BuLi.

Flexible ethylene-bridged bis(amidines) and bis(amidinates) as versatile supramolecular assemblies and photoluminescent switches

ACS Fall 2021

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