title: Self-assembly of a [2]pseudorota[3]catenane in water.
abstract: A donor-acceptor [3]catenane incorporating two cyclobis(paraquat-p-phenylene) rings linked together by a dinaphtho[50]crown-14 macrocycle possesses a π-electron-deficient pocket. Contrary to expectation, negligible binding of a hexaethylene glycol chain interrupted in its midriff by a π-electron-rich 1,5-dioxynaphthalene unit was observed in acetonitrile. However, a fortuitous solid-state superstructure of the expected 1:1 complex revealed its inability to embrace any stabilizing [C-H···O] interactions between the clearly unwelcome guest and the host reluctantly accommodating it. By contrast, in aqueous solution, the 1:1 complex becomes very stable thanks to the intervention of hydrophobic bonding.
authors.affiliation: Center for the Chemistry of Integrated Systems, Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3133, USA.
authors.forename: Ross S
authors.initials: RS
authors.lastname: Forgan
authors.forename: Jeremiah J
authors.initials: JJ
authors.lastname: Gassensmith
authors.forename: David B
authors.initials: DB
authors.lastname: Cordes
authors.forename: Megan M
authors.initials: MM
authors.lastname: Boyle
authors.forename: Karel J
authors.initials: KJ
authors.lastname: Hartlieb
authors.forename: Douglas C
authors.initials: DC
authors.lastname: Friedman
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: J Fraser
authors.initials: JF
authors.lastname: Stoddart
mesh_terms: D000873:Anthracenes / Q000737:chemistry*; D008958:Models, Molecular; D014867:Water / Q000737:chemistry*
chemical_list: D000873:Anthracenes; C467767:catenane; D014867:Water