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Heterocyclic [9]Hel...
Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence
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- Warthegau, Stefan S. (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Hillers-Bendtsen, Andreas E. (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Pedersen, Stephan K. (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Rindom, Cecilie (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Bræstrup, Christoffer (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Jensen, Jeppe S. (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Hammerich, Ole (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Thomsen, Maria S. (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Kamounah, Fadhil S. (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Norman, Patrick (author)
- KTH,Teoretisk kemi och biologi
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- Mikkelsen, Kurt V. (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Brock-Nannestad, Theis (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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- Pittelkow, Michael (author)
- Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen Ø, Denmark, Universitetsparken 5
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(creator_code:org_t)
- Wiley, 2023
- 2023
- English.
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In: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 29:58
- Related links:
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https://doi.org/10.1...
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https://urn.kb.se/re...
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Abstract
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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.
Subject headings
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
Keyword
- CD spectroscopy
- CPL spectroscopy
- helicenes
- heterocycles
- X-ray crystallography
Publication and Content Type
- ref (subject category)
- art (subject category)
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Warthegau, Stefa ...
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Hillers-Bendtsen ...
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Pedersen, Stepha ...
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Rindom, Cecilie
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Bræstrup, Christ ...
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Jensen, Jeppe S.
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Hammerich, Ole
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Thomsen, Maria S ...
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Kamounah, Fadhil ...
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Norman, Patrick
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Mikkelsen, Kurt ...
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Brock-Nannestad, ...
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Pittelkow, Micha ...
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- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Theoretical Chem ...
- Articles in the publication
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Chemistry - A Eu ...
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Royal Institute of Technology