Acylphosphates as versatile transient species in reaction networks and optical catalyst screenings
Andreas Englert, Felix Majer, Jannik Schiessl, Alexander J. C. Kuehne, Max von Delius
Abstract
Chemically driven reaction cycles are prevalent in nature; yet, artificial examples are still rare and often lack robustness or versatility. In this study, we introduce acylphosphate steady states that can be accessed from a wide range of organophosphates using either carboxylic anhydride or carbodiimide fuels. The combination of carboxylic anhydride fuel and pyridine catalysis makes this chemistry sufficiently robust to allow for 25 fueling cycles without generation of observable quantities of detrimental side products such as pyrophosphates. We demonstrate that the acylation of organophosphates gives rise to transient aggregates, and we harness the transient fluorescence of acylphosphate-bridged excimers in rapid screenings of more than 50 catalysts in a single well plate experiment. Due to its versatility and robustness, we anticipate that the organophosphate/acylphosphate reaction cycle will prove useful for the creation of chemically driven molecular machines and transient self-assemblies.