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Triggering Emission with the Helical Turn in Thiadiazole-Helicenes

Abstract : Introduction of heterocycles into the helical skeleton of helicenes allows modulation of their redox, chiroptical, and photophysical properties. This paper describes the straightforward preparation and structural characterization by single-crystal X-ray diffraction of thiadiazole-[7]helicene, which was resolved into M and P enantiomers by chiral HPLC, together with its S-shaped double [4]helicene isomer, as well as the smaller congeners thiadiazole-[5]helicene and benzothiadiazole-anthracene. A copper(II) complex with two thiadiazole-[5]helicene ligands was structurally characterized, and it shows the presence of both M and P isomers coordinated to the metal center. The emission properties of the heterohelicenes are highly dependent on the helical turn, as the [7]- and [5]helicene are poorly emissive, whereas their isomers, that is, the S-shaped double [4]helicene and thiadiazole-benzanthracene, are luminescent, with quantum efficiencies of 5.4 and 6.5 %, respectively. DFT calculations suggest quenching of the luminescence of enantiopure [7]helicenes through an intersystem-crossing mechanism arising from the relaxed excited S1 state.
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Contributor : Pierre-Antoine Bouit <>
Submitted on : Wednesday, January 4, 2017 - 9:40:17 AM
Last modification on : Wednesday, April 7, 2021 - 3:18:08 PM
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Thomas Biet, Kevin Martin, Jihane Hankache, Nora Hellou, Andreas Hauser, et al.. Triggering Emission with the Helical Turn in Thiadiazole-Helicenes. Chemistry - A European Journal, Wiley-VCH Verlag, 2017, 32 (2), pp.437-446. ⟨10.1002/chem.201604471⟩. ⟨hal-01406346⟩



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