Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence

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Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence. / Warthegau, Stefan S.; Hillers-Bendtsen, Andreas E.; Pedersen, Stephan K.; Rindom, Cecilie; Bræstrup, Christoffer; Jensen, Jeppe S.; Hammerich, Ole; Thomsen, Maria S.; Kamounah, Fadhil S.; Norman, Patrick; Mikkelsen, Kurt V.; Brock-Nannestad, Theis; Pittelkow, Michael.

I: Chemistry - A European Journal, Bind 29, Nr. 58, e202301815, 2023.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Warthegau, SS, Hillers-Bendtsen, AE, Pedersen, SK, Rindom, C, Bræstrup, C, Jensen, JS, Hammerich, O, Thomsen, MS, Kamounah, FS, Norman, P, Mikkelsen, KV, Brock-Nannestad, T & Pittelkow, M 2023, 'Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence', Chemistry - A European Journal, bind 29, nr. 58, e202301815. https://doi.org/10.1002/chem.202301815

APA

Warthegau, S. S., Hillers-Bendtsen, A. E., Pedersen, S. K., Rindom, C., Bræstrup, C., Jensen, J. S., Hammerich, O., Thomsen, M. S., Kamounah, F. S., Norman, P., Mikkelsen, K. V., Brock-Nannestad, T., & Pittelkow, M. (2023). Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence. Chemistry - A European Journal, 29(58), [e202301815]. https://doi.org/10.1002/chem.202301815

Vancouver

Warthegau SS, Hillers-Bendtsen AE, Pedersen SK, Rindom C, Bræstrup C, Jensen JS o.a. Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence. Chemistry - A European Journal. 2023;29(58). e202301815. https://doi.org/10.1002/chem.202301815

Author

Warthegau, Stefan S. ; Hillers-Bendtsen, Andreas E. ; Pedersen, Stephan K. ; Rindom, Cecilie ; Bræstrup, Christoffer ; Jensen, Jeppe S. ; Hammerich, Ole ; Thomsen, Maria S. ; Kamounah, Fadhil S. ; Norman, Patrick ; Mikkelsen, Kurt V. ; Brock-Nannestad, Theis ; Pittelkow, Michael. / Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence. I: Chemistry - A European Journal. 2023 ; Bind 29, Nr. 58.

Bibtex

@article{8d34c772bae94659adfe3e0d469b3b85,

title = "Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence",

abstract = "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.",

keywords = "CD spectroscopy, CPL spectroscopy, helicenes, heterocycles, X-ray crystallography",

author = "Warthegau, {Stefan S.} and Hillers-Bendtsen, {Andreas E.} and Pedersen, {Stephan K.} and Cecilie Rindom and Christoffer Br{\ae}strup and Jensen, {Jeppe S.} and Ole Hammerich and Thomsen, {Maria S.} and Kamounah, {Fadhil S.} and Patrick Norman and Mikkelsen, {Kurt V.} and Theis Brock-Nannestad and Michael Pittelkow",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.",

year = "2023",

doi = "10.1002/chem.202301815",

language = "English",

volume = "29",

journal = "Chemistry: A European Journal",

issn = "0947-6539",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "58",

}

RIS

TY - JOUR

T1 - Heterocyclic [9]Helicenes Exhibiting Bright Circularly Polarized Luminescence

AU - Warthegau, Stefan S.

AU - Hillers-Bendtsen, Andreas E.

AU - Pedersen, Stephan K.

AU - Rindom, Cecilie

AU - Bræstrup, Christoffer

AU - Jensen, Jeppe S.

AU - Hammerich, Ole

AU - Thomsen, Maria S.

AU - Kamounah, Fadhil S.

AU - Norman, Patrick

AU - Mikkelsen, Kurt V.

AU - Brock-Nannestad, Theis

AU - Pittelkow, Michael

PY - 2023

Y1 - 2023

N2 - 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.

AB - 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.

KW - CD spectroscopy

KW - CPL spectroscopy

KW - helicenes

KW - heterocycles

KW - X-ray crystallography

U2 - 10.1002/chem.202301815

DO - 10.1002/chem.202301815

M3 - Journal article

C2 - 37458527

AN - SCOPUS:85170532730

VL - 29

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 58

M1 - e202301815

ER -

ID: 371017920

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