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Circularly Polarised Luminescence from Helically Chiral “Confused” N , N , O , C ‐Boron‐Chelated Dipyrromethenes (BODIPYs)
Author(s) -
Clarke Rebecca,
Ho Kin Lok,
Alsimaree Abdulrahman Abdullah,
Woodford Owen J.,
Waddell Paul G.,
Bogaerts Jonathan,
Herrebout Wouter,
Knight Julian G.,
Pal Robert,
Penfold Thomas J.,
Hall Michael J.
Publication year - 2017
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201700106
Subject(s) - bodipy , boron , chelation , enantiomer , luminescence , chemistry , circular dichroism , crystallography , stereochemistry , materials science , organic chemistry , physics , fluorescence , optoelectronics , optics
Chiral organic fluorophores have significant promise in the development of efficient emitters of circularly polarized light. Herein we describe a helically chiral boron dipyrromethene (BODIPY) with a hitherto unreported N , N , O , C ‐boron‐chelation motif, synthesised by means of a one‐pot boron metathesis, nucleophilic aromatic substitution (S N Ar), Suzuki coupling, boron chelation, cascade reaction. Resolution of the racemic BODIPY (by preparative HPLC on a chiral stationary phase) allowed examination of the chiroptical properties of the resulting enantiomers ( λ max (abs)=593 nm, λ max (em)=622 nm, ϵ =30 000 m −1 cm −1 , φ F =0.49, |g lum |=3.7×10 −3 (hexane)). This is the first example of circularly polarised emission from a non‐ C 2 ‐symmetric helically chiral N , N , O , C ‐BODIPY and as such provides a valuable benchmark for future developments in this compound series.