title: Synthesis of fluorescent naphthoquinolizines via intramolecular Houben-Hoesch reaction.
abstract: The repertoire of synthetic methods leading to aza-analogues of polycyclic aromatic heterocycles has been enlarged by the discovery of the rearrangement of 10-substituted benzo[h]quinolines into compounds bearing an azonia-pyrene moiety. Acid-mediated intramolecular cyclization of derivatives bearing -CH2 CN and -CH2 CO2 Et groups led to compounds bearing a 5-substituted benzo[de]pyrido[3,2,1-ij]quinolinium core. Advanced photophysical studies including time-correlated single photon counting (TCSPC) and transient absorption spectroscopy of 5-aminobenzo[de]pyrido[3,2,1-ij]quinolin-4-ium salt and 5H-benzo[de]pyrido[3,2,1-ij]quinolin-5-one showed their promising optical properties such as high fluorescence quantum yields (37-59%), which was almost independent of the solvent, and high tenability of the absorption band position upon changing the solvent. The benzo[de]pyrido[3,2,1-ij]quinolinium salt selectively stains nucleic acids (in the nucleus and mitochondria) in eukaryotic cells.
authors.affiliation: Warsaw University of Technology Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw (Poland); Warsaw University, Department of Chemistry, Pasteura 1, 01-173 Warsaw (Poland).
authors.forename: Anton J
authors.initials: AJ
authors.lastname: Stasyuk
authors.forename: Sabina
authors.initials: S
authors.lastname: Smoleń
authors.forename: Eliza
authors.initials: E
authors.lastname: Glodkowska-Mrowka
authors.forename: Wojciech
authors.initials: W
authors.lastname: Brutkowski
authors.forename: Michał K
authors.initials: MK
authors.lastname: Cyrański
authors.forename: Nikolai
authors.initials: N
authors.lastname: Tkachenko
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Gryko
mesh_terms: D005456:Fluorescent Dyes / Q000737:chemistry*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D011807:Quinolizines / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D011084:Polycyclic Aromatic Hydrocarbons; D011807:Quinolizines
keywords: cyclization; fluorescence; heterocycles; pyrenes; quinolines