title: Preparation and pH-switching of fluorescent borylated arylisoquinolines for multilevel molecular logic.
abstract: The preparation of pH-switchable fluorescent borylated arylisoquinoline dyes via a flexible iridium-catalyzed route is reported. The obtained dyes feature aromatic amino substitution and lateral aliphatic amino groups as electron donors. The photophysical properties of the internal charge transfer dyes were studied, which was complemented by density functional theory calculations. Appreciable fluorescence quantum yields (Φf up to ca. 0.4) and characteristic spectral fingerprints in the green to red emission range were observed. The fluorescence modulation upon multiple and orthogonal protonation with triflic acid was studied and led to the interpretation of multilevel switching including off-on-off, ternary, and quaternary responses.
authors.affiliation: CIQSO-Center for Research in Sustainable Chemistry and Department of Chemical Engineering, Physical Chemistry, and Organic Chemistry, University of Huelva, Campus de El Carmen s/n, 21071 Huelva, Spain.
authors.forename: Vânia F
authors.initials: VF
authors.lastname: Pais
authors.forename: Mauricio
authors.initials: M
authors.lastname: Lineros
authors.forename: Rocío
authors.initials: R
authors.lastname: López-Rodríguez
authors.forename: Hamdy S
authors.initials: HS
authors.lastname: El-Sheshtawy
authors.forename: Rosario
authors.initials: R
authors.lastname: Fernández
authors.forename: José M
authors.initials: JM
authors.lastname: Lassaletta
authors.forename: Abel
authors.initials: A
authors.lastname: Ros
authors.forename: Uwe
authors.initials: U
authors.lastname: Pischel
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D005453:Fluorescence; D006863:Hydrogen-Ion Concentration; D007495:Iridium / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D001896:Boron Compounds; D007546:Isoquinolines; D007495:Iridium