Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence
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We describe a concise synthetic strategy for the preparation of heterocyclic [9]helicenes and a simple preparative-scale protocol for the optical resolution of the resulting M- and P-enantiomers. The helicenes were characterized by single-crystal X-ray diffraction along with a range of spectroscopic and computational techniques. A fluorescence quantum yield of up to 65 % was observed, and the chiroptical properties of both M- and P-helicenes revealed large dissymmetry factors. The circularly polarized luminescence brightness reaches up to 17 M−1 cm−1, as measured experimentally and verified computationally, which makes this the highest circularly polarized luminescence brightness among heterocyclic helicenes. We describe how chiroptical properties (both circular dichroism and circularly polarized luminescence) can be described and predicted using quantum chemical calculations. The synthetic approach also reveals by-products that originate from internal oxidation reactions, presumably mediated by the close proximity of the π-surfaces in the helicene structure.
Originalsprog | Engelsk |
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Artikelnummer | e202301815 |
Tidsskrift | Chemistry - A European Journal |
Vol/bind | 29 |
Udgave nummer | 58 |
Antal sider | 6 |
ISSN | 0947-6539 |
DOI | |
Status | Udgivet - 2023 |
Bibliografisk note
Funding Information:
Financial support from the Danish Council for Independent Research (DFF 4181‐00206 and 9040‐00265) and from the University of Copenhagen is acknowledged. KVM acknowledges the Danish Council for Independent Research, DFF‐0136‐00081 B, and the European Union's Horizon 2020 Framework Programme under grant agreement number 951801 for financial support. We thank Dr. Nicolaj Kofod for assistance with the quantum yield measurements and determinations.
Publisher Copyright:
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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