Highly efficient cucurbit[8]uril-templated intramolecular photocycloaddition of 2-naphthalene-labeled poly(ethylene glycol) in aqueous solution.
The photodimerization of water-insoluble 2-naphthalene-labeled poly(ethyl glycol) (N-Pn-N) in cucurbit[8]uril (CB[8]) aqueous solution was investigated. UV-vis, fluorescence, and 1H NMR analysis reveal that CB[8] can encapsulate N-Pn-N to make a stable 1:1 inclusion complex N-Pn-N@CB[8] in aqueous solution. Irradiation of N-Pn-N in the CB[8] aqueous solution results in intramolecular photocycloaddition with remarkable selectivity and efficiency, whereas no photodimer could be detected in host-free solution.
D001952:Bridged-Ring Compounds / Q000737:chemistry / Q000528:radiation effects*; D003500:Cyclization; D019281:Dimerization; D007093:Imidazoles / Q000737:chemistry / Q000528:radiation effects*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000528:radiation effects*; D010777:Photochemistry; D011092:Polyethylene Glycols / Q000737:chemistry / Q000528:radiation effects*; D012996:Solutions / Q000737:chemistry / Q000528:radiation effects; D013050:Spectrometry, Fluorescence; D014466:Ultraviolet Rays; D014867:Water / Q000737:chemistry; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
D001952:Bridged-Ring Compounds; D007093:Imidazoles; D009281:Naphthalenes; D011092:Polyethylene Glycols; D012996:Solutions; D014867:Water; C507198:cucurbit(8)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils; C031721:naphthalene