title: Circularly Polarized Luminescence from Helically Chiral N,N,O,O-Boron-Chelated Dipyrromethenes.
abstract: Helically chiral N,N,O,O-boron chelated dipyrromethenes showed solution-phase circularly polarized luminescence (CPL) in the red region of the visible spectrum (λem (max) from 621 to 663 nm). The parent dipyrromethene is desymmetrised through O chelation of boron by the 3,5-ortho-phenolic substituents, inducing a helical chirality in the fluorophore. The combination of high luminescence dissymmetry factors (|glum | up to 4.7 ×10(-3) ) and fluorescence quantum yields (ΦF up to 0.73) gave exceptionally efficient circularly polarized red emission from these simple small organic fluorophores, enabling future application in CPL-based bioimaging.
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK).
authors.forename: Rua B
authors.initials: RB
authors.lastname: Alnoman
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK).
authors.forename: Sandra
authors.initials: S
authors.lastname: Rihn
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK).
authors.forename: Daniel C
authors.initials: DC
authors.lastname: O'Connor
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK).
authors.forename: Fiona A
authors.initials: FA
authors.lastname: Black
authors.affiliation: Applied Photophysics Ltd., 21 Mole Business Park, Leatherhead, Surrey KT22 7BA (UK).
authors.forename: Bernard
authors.initials: B
authors.lastname: Costello
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK).
authors.forename: Paul G
authors.initials: PG
authors.lastname: Waddell
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK).
authors.forename: William
authors.initials: W
authors.lastname: Clegg
authors.affiliation: School of Chemistry, University of Glasgow, Joseph Black Building. University Avenue, Glasgow, G12 8QQ, Scotland (UK).
authors.forename: Robert D
authors.initials: RD
authors.lastname: Peacock
authors.affiliation: Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium).
authors.forename: Wouter
authors.initials: W
authors.lastname: Herrebout
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK). julian.knight@ncl.ac.uk.
authors.forename: Julian G
authors.initials: JG
authors.lastname: Knight
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK). m.hall@ncl.ac.uk.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Hall
mesh_terms: D001895:Boron / Q000737:chemistry*; D002614:Chelating Agents; D002942:Circular Dichroism; D005456:Fluorescent Dyes / Q000737:chemistry*; D049449:Luminescence; D008163:Luminescent Measurements / Q000379:methods; D015394:Molecular Structure; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry; D012996:Solutions; D013237:Stereoisomerism
chemical_list: D002614:Chelating Agents; D005456:Fluorescent Dyes; D012996:Solutions; C507544:dipyrromethene; D011162:Porphobilinogen; D001895:Boron
keywords: BODIPYs; absolute stereochemistry; chirality; circularly polarized luminescence; luminescence