Guest Exchange by a Partial Energy Ratchet in Water

Xue L Yang (1) , Qian R Cheng (2) , Valerie Monnier (3) , Laurence Charles (1) , Hakim Karoui (1) , Olivier Ouari (1) , Didier Gigmes (1) , Ruibing Wang (2) , Anthony Kermagoret (1) , David Bardelang (1)

1 ICR - Institut de Chimie Radicalaire
2 State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa, Macau, China
3 AMU SPEC - Spectropôle - Aix Marseille Université

Molecular machines are ubiquitous in nature and function away from equilibrium by consuming fuels to produce appropriate work. Chemists have recently excelled at mimicking the fantastic job performed by natural molecular machines with synthetic systems soluble in organic solvents. In efforts toward analogous systems working in water, we show that guest molecules can be exchanged in the synthetic macrocycle cucurbit[7]uril by involving kinetic traps, and in such a way as modulating energy wells and kinetic barriers using pH, light and redox stimuli. Ditolyl-viologen can also be exchanged using the best kinetic trap and interfaced with alginate thus affording pH-responsive blue, fluorescent hydrogels. With tunable rate and binding constants toward relevant guests, cucurbiturils may become excellent ring molecules for the construction of advanced molecular machines working in water.

Keywords: cucurbituril; host–guest interactions; ratchet; supramolecular chemistry; water

Domains: Chemical Sciences

Xue L Yang, Qian R Cheng, Valerie Monnier, Laurence Charles, Hakim Karoui, et al.. Guest Exchange by a Partial Energy Ratchet in Water. Angewandte Chemie International Edition, 2021, 60 (12), pp.6617-6623. ⟨10.1002/anie.202014399⟩. ⟨hal-03227446⟩