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3226067 
Journal Article 
Efficient host-guest energy transfer in polycationic cyclophane-perylene diimide complexes in water 
Ryan, ST; Del Barrio, J; Ghosh, I; Biedermann, F; Lazar, AI; Lan, Y; Coulston, RJ; Nau, WM; Scherman, OA 
2014 
Yes 
Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126 
136 
25 
9053-9060 
English 
24893200 
WOS:000338184200037 
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.