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      Circularly Polarized Luminescence from Helically Chiral N, N, O, O‐Boron‐Chelated Dipyrromethenes

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          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 ( λ em(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 (| g lum| up to 4.7 ×10 −3) and fluorescence quantum yields ( Φ F up to 0.73) gave exceptionally efficient circularly polarized red emission from these simple small organic fluorophores, enabling future application in CPL‐based bioimaging.

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          Most cited references20

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          Lanthanide complexes as chiral probes exploiting circularly polarized luminescence.

          Optical probes that provide information about local chirality have been developed based on changes to the circular polarisation of emitted light. Highly emissive complexes of lanthanide ions are ideally suited for CPL spectroscopy and the design criteria for developing such probes are defined, based on a rigorous stereochemical analysis. The perturbation of a dynamically racemic complex may occur either by a change in complex constitution or by non-covalent association. With complexes of enantiopure ligands, perturbation may involve either dynamic helicity inversion or a reversible change in the lanthanide coordination environment.
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            Lanthanide probes for bioresponsive imaging.

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              Being excited by lanthanide coordination complexes: aqua species, chirality, excited-state chemistry, and exchange dynamics.

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                Author and article information

                Contributors
                julian.knight@ncl.ac.uk
                m.hall@ncl.ac.uk
                Journal
                Chemistry
                Chemistry
                10.1002/(ISSN)1521-3765
                CHEM
                Chemistry (Weinheim an Der Bergstrasse, Germany)
                WILEY‐VCH Verlag (Weinheim )
                0947-6539
                1521-3765
                30 November 2015
                04 January 2016
                : 22
                : 1 ( doiID: 10.1002/chem.v22.1 )
                : 93-96
                Affiliations
                [ 1 ]School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK)
                [ 2 ]Applied Photophysics Ltd., 21 Mole Business Park, Leatherhead, Surrey KT22 7BA (UK)
                [ 3 ]School of Chemistry, University of Glasgow, Joseph Black Building. University Avenue, Glasgow, G12 8QQ, Scotland (UK)
                [ 4 ]Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium)
                Author notes
                [*] [* ]School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU (UK)
                Article
                CHEM201504484
                10.1002/chem.201504484
                4736443
                26555772
                4b006cfd-e2e9-499b-8019-3475b8aad821
                © 2015 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

                Open access.

                History
                : 09 November 2015
                Page count
                Figures: 8, Tables: 0, References: 72, Pages: 4
                Funding
                Funded by: Funded Access
                Funded by: Newcastle University (NCL)
                Funded by: BBSRC
                Award ID: BB/K013971/1
                Funded by: Department of Chemistry, Faculty of Science, Taibah University, Saudi Arabia
                Funded by: EPSRC
                Award ID: EP/F03637X/1
                Funded by: Diamond Light Source
                Categories
                Communication
                Communications
                Chirality
                Custom metadata
                2.0
                January 4, 2016
                Converter:WILEY_ML3GV2_TO_NLMPMC version:4.7.5 mode:remove_FC converted:28.01.2016

                Chemistry
                absolute stereochemistry,bodipys,chirality,circularly polarized luminescence,luminescence

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