title: Synthesis, characterization, and photophysical study of fluorescent N-substituted benzo[ghi]perylene "swallow tail" monoimides.
abstract: A set of N-substituted benzoperylene monoimide (BPI) fluorophores was synthesized and characterized structurally and photophysically. Condensation of benzo[ghi]perylene-1,2-dicarboxylic anhydride in the presence of "swallow tail" alkyl amines produced fluorophores that are soluble in a range of organic solvents, highly absorbing in the near-UV (ε(334) = 79,000 M(-1) cm(-1)), and fluorescent in the visible range. Photophysical behavior of the compounds was studied with steady-state and time-correlated single photon counting. The synthesized BPIs exhibit positive solvachromatic emission (λ(em) (hexane) = 469 nm; λ(em) (ethanol) = 550 nm) as a function of solvent polarity with little change in their excited-state lifetime (9.6-6.5 ns) and fluorescence quantum yield (0.27-0.44) over the polarity range studied. Solvachromatic shifts were analyzed using the Lippert-Mataga approach. In nonpolar hydrocarbon solvents evidence of dual emission from closely spaced (562 cm(-1)) S(1) and S(2) excited states is observed. Preliminary peak assignments for the anomalous S(2) emission are made.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, Maryland 21250, USA.
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Manning
authors.forename: William
authors.initials: W
authors.lastname: Bogen
authors.forename: Lisa A
authors.initials: LA
authors.lastname: Kelly
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010777:Photochemistry; D013050:Spectrometry, Fluorescence
chemical_list: D000473:Alkanes; D000588:Amines; D005456:Fluorescent Dyes; D007094:Imides; C006706:benzoperylene; D010569:Perylene