Small-molecule recognition for controlling molecular motion in hydrogen-bond-assembled rotaxanes.
Di(acylamino)pyridines successfully template the formation of hydrogen-bonded rotaxanes through five-component clipping reactions. A solid-state study showed the participation of the pyridine nitrogen atom in the stabilization of the mechanical bond between the thread and the benzylic amide macrocycle. The addition of external complementary binders to a series of interlocked bis(2,6-di(acylamino)pyridines) promoted restraint of the back and forward ring motion. The original translation can be restored through a competitive recognition event by the addition of a preorganized bis(di(acylamino)pyridine) that forms stronger ADA-DAD complexes with the external binders.
Departamento de Química Orgánica, Facultad de Química, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, E-30100 Murcia (Spain).
Alberto
A
Martinez-Cuezva
Jose
J
Berna
Raul-Angel
RA
Orenes
Aurelia
A
Pastor
Mateo
M
Alajarin
D001665:Binding Sites; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D011725:Pyridines / Q000737:chemistry; D043862:Rotaxanes / Q000737:chemistry*
D011725:Pyridines; D043862:Rotaxanes; C023666:pyridine
Brownian motion; competitive binding; hydrogen-bond arrays; rotaxanes; template synthesis