Dynamic combinatorial discovery of a [2]-catenane and its guest-induced conversion into a molecular square host.
A simple water-soluble naphthalenedithiol building block is converted quantitatively into a series of octameric [2]-catenanes, composed of two interlocked molecular squares. When this mixture is re-equilibrated in the presence of an adamantyl ammonium guest, the catenanes disassemble into their macrocyclic components that bind the guest with nanomolar affinity in water.
West
Kevin R
KR
University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge CB2 1EW, United Kingdom.
Ludlow
R Fred
RF
Corbett
Peter T
PT
Besenius
Pol
P
Mansfeld
Friederike M
FM
Cormack
Peter A G
PA
Sherrington
David C
DC
Goodman
Jonathan M
JM
Stuart
Marc C A
MC
Otto
Sijbren
S
D043863:Catenanes / Q000138:chemical synthesis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D010316:Particle Size; D012995:Solubility; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D043863:Catenanes; D013438:Sulfhydryl Compounds; D014867:Water