title: A Modular Class of Fluorescent Difluoroboranes: Synthesis, Structure, Optical Properties, Theoretical Calculations and Applications for Biological Imaging.
abstract: Ten borylated bipyridines (BOBIPYs) have been synthesized and selected structural modifications have been made that allow useful structure-optical property relationships to be gathered. These systems have been further investigated using DFT calculations and spectroscopic measurements, showing blue to green fluorescence with quantum yields up to 41 %. They allow full mapping of the structure to determine where selected functionalities can be implemented, to tune the optical properties or to incorporate linking groups. The best derivative was thus functionalised with an alkyne linker, which would enable further applications through click chemistry and in this optic, the stability of the fluorophores has been evaluated.
authors.affiliation: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK.|Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Sylvestre P J T
authors.initials: SP
authors.lastname: Bachollet
authors.affiliation: Cynora GmbH, Werner-von-Siemens-Straße 2-6, 76646, Bruchsal, Germany.
authors.forename: Daniel
authors.initials: D
authors.lastname: Volz
authors.affiliation: Departamento de Química Organica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018, San Sebastian, Spain.
authors.forename: Béla
authors.initials: B
authors.lastname: Fiser
authors.affiliation: Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Stephan
authors.initials: S
authors.lastname: Münch
authors.affiliation: Institute of Toxicology and Genetics, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.
authors.forename: Franziska
authors.initials: F
authors.lastname: Rönicke
authors.affiliation: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK.
authors.forename: Jokin
authors.initials: J
authors.lastname: Carrillo
authors.affiliation: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK.
authors.forename: Harry
authors.initials: H
authors.lastname: Adams
authors.affiliation: Institute of Toxicology and Genetics, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.
authors.forename: Ute
authors.initials: U
authors.lastname: Schepers
authors.affiliation: Departamento de Química Organica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018, San Sebastian, Spain.
authors.forename: Enrique
authors.initials: E
authors.lastname: Gómez-Bengoa
authors.affiliation: Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany. stefan.braese@kit.edu.|Institute of Toxicology and Genetics, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany. stefan.braese@kit.edu.
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
authors.affiliation: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK. j.harrity@sheffield.ac.uk.
authors.forename: Joseph P A
authors.initials: JP
authors.lastname: Harrity
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D057930:Click Chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001881:Borates; D005456:Fluorescent Dyes; C098759:fluoroboric acid
keywords: borylated bipyridines; cell imaging; density functional calculations; fluorophore; photophysics