title: Efficient host-guest energy transfer in polycationic cyclophane-perylene diimide complexes in water.
abstract: We report the self-assembly of a series of highly charged supramolecular complexes in aqueous media composed of cyclobis(4,4'-(1,4-phenylene)bispyridine-p-phenylene)tetrakis(chloride) (ExBox) and three dicationic perylene diimides (PDIs). Efficient energy transfer (ET) is observed between the host and guests. Additionally, we show that our hexacationic complexes are capable of further complexation with neutral cucurbit[7]uril (CB[7]), producing a 3-polypseudorotaxane via the self-assembly of orthogonal recognition moieties. ExBox serves as the central ring, complexing to the PDI core, while two CB[7]s behave as supramolecular stoppers, binding to the two outer quaternary ammonium motifs. The formation of the 3-polypseudorotaxane results in far superior photophysical properties of the central PDI unit relative to the binary complexes at stoichiometric ratios. Lastly, we also demonstrate the ability of our binary complexes to act as a highly selective chemosensing ensemble for the neurotransmitter melatonin.
authors.affiliation: Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, United Kingdom.
authors.forename: Seán T J
authors.initials: ST
authors.lastname: Ryan
authors.forename: Jesús
authors.initials: J
authors.lastname: Del Barrio
authors.forename: Indrajit
authors.initials: I
authors.lastname: Ghosh
authors.forename: Frank
authors.initials: F
authors.lastname: Biedermann
authors.forename: Alexandra I
authors.initials: AI
authors.lastname: Lazar
authors.forename: Yang
authors.initials: Y
authors.lastname: Lan
authors.forename: Roger J
authors.initials: RJ
authors.lastname: Coulston
authors.forename: Werner M
authors.initials: WM
authors.lastname: Nau
authors.forename: Oren A
authors.initials: OA
authors.lastname: Scherman
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D004735:Energy Transfer; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry*
chemical_list: D001952:Bridged-Ring Compounds; D002412:Cations; D007094:Imides; D011108:Polymers; D011726:Pyridinium Compounds; C000597595:cyclobis(4,4'-(1,4-phenylene)bispyridine-p-phenylene)tetrakis(chloride); C521332:perylenediimide; D010569:Perylene