title: Intramolecular Hydrogen-Bonding Effects on the Fluorescence of PRODAN Derivatives.
abstract: The effects of intramolecular hydrogen-bonding on the fluorescence behavior of three derivatives of 6-propionyl-2-dimethylaminonaphthalene are reported. The H-bonding effects are revealed through comparisons with corresponding reference compounds in which the H-bond-donating hydroxyl groups are replaced with methoxy groups. In toluene, intramolecular H bonding gives rise to a dramatic increase in the fluorescence intensity but only a slight red shift in the position. This behavior is attributed to decreased efficiency in intersystem crossing due to an increase in the energy of the n → π* triplet state. The intramolecular H bond does not induce quenching in acetonitrile; however, in the presence of a very small concentration of methanol, a dual intramolecular, intermolecular H-bonding arrangement does lead to partial quenching as revealed by preferential solvation studies.
authors.affiliation: Department of Chemistry, College of William and Mary , Williamsburg, Virginia 23185, United States.
authors.forename: Isaac G
authors.initials: IG
authors.lastname: Alty
authors.affiliation: Department of Chemistry, College of William and Mary , Williamsburg, Virginia 23185, United States.
authors.forename: Douglas W
authors.initials: DW
authors.lastname: Cheek
authors.affiliation: Department of Chemistry, College of William and Mary , Williamsburg, Virginia 23185, United States.
authors.forename: Tao
authors.initials: T
authors.lastname: Chen
authors.affiliation: Department of Chemistry, College of William and Mary , Williamsburg, Virginia 23185, United States.
authors.forename: David B
authors.initials: DB
authors.lastname: Smith
authors.affiliation: Department of Chemistry, College of William and Mary , Williamsburg, Virginia 23185, United States.
authors.forename: Emma Q
authors.initials: EQ
authors.lastname: Walhout
authors.affiliation: Department of Chemistry, College of William and Mary , Williamsburg, Virginia 23185, United States.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Abelt