title: Study of the fluorescent properties of partially hydrogenated 1,1'-bi-2-naphthol-amine molecules and their use for enantioselective fluorescent recognition.
abstract: The fluorescent properties of a series of H(8)BINOL-amine compounds are investigated. It is revealed that the intramolecular hydrogen bonds of these compounds contribute to the shift of the emission of their H(8)BINOL unit to a much longer wavelength. That is, the emission of H(8)BINOL is at λ = 323 nm, but that of the H(8)BINOL-amino alcohol (S)-5 is at λ = 390 nm. Binding of (S)-5 with mandelic acid suppresses its intramolecular hydrogen bonding and restores the short wavelength emission of the H(8)BINOL unit. When (S)-5 (1.0 × 10(-4) in CH(2)Cl(2)) was treated with (R)-mandelic acid (4.0 × 10(-3)), a large fluorescence enhancement at the short wavelength (λ(emi) = 330 nm) was observed with I(R)/I(0) = 11.7. When (S)-MA was used under the same conditions, the enhancement at the short wavelength emission was much smaller. Thus, a good enantioselective fluorescent response was observed with ef =3.5 [ef: enantioselective fluorescence enhancement ratio = (I(R) - I(0))/(I(S) - I(0))]. This study demonstrates that the H(8)BINOL-based molecules are promising as a new class of enantioselective fluorescent sensors.
authors.affiliation: Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, United States.
authors.forename: Shanshan
authors.initials: S
authors.lastname: Yu
authors.forename: Albert M
authors.initials: AM
authors.lastname: DeBerardinis
authors.forename: Mark
authors.initials: M
authors.lastname: Turlington
authors.forename: Lin
authors.initials: L
authors.lastname: Pu
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry; D005453:Fluorescence; D006859:Hydrogen / Q000737:chemistry*; D006860:Hydrogen Bonding; D006865:Hydrogenation; D008333:Mandelic Acids / Q000737:chemistry; D008958:Models, Molecular; D015335:Molecular Probes / Q000032:analysis / Q000138:chemical synthesis*; D015394:Molecular Structure; D009284:Naphthols / Q000032:analysis / Q000138:chemical synthesis*; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000605:Amino Alcohols; D008333:Mandelic Acids; D015335:Molecular Probes; D009284:Naphthols; C412332:1,1'-bi-2-naphthol; D006859:Hydrogen; C037938:mandelic acid