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Article Dans Une Revue Chirality Année : 2023

Tuning the photophysical and chiroptical properties of [4]helicene‐diketopyrrolopyrroles

Maurizio Mastropasqua Talamo
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Thomas Cauchy
Flavia Pop
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Narcis Avarvari
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Résumé

Synthesis and functionalization of diketopyrrolo[3,4‐ c ]pyrrole (DPP) derivatives containing chiral groups able to induce a strong chiral perturbation of the DPP core are still a challenging task. We report in this work the straightforward preparation of four bis([4]helicene)‐DPP and bis([4]thiahelicene)‐DPP dyes upon the condensation of 2‐CN‐[4](thia)helicene precursors, followed by their N‐alkylation by nucleophilic substitution (compounds 9 – 11 ) or by a Mitsunobu‐type strategy (compound 12 ). Compound 12 , which contains sec ‐phenylethyl groups attached to the nitrogen atoms, has been obtained as ( R , R ) and ( S , S ) enantiomers. The four DPP‐helicenes are luminescent in solution, while the N‐benzyl ( 10 ) and N ‐ sec ‐phenethyl ( 12 ) are emissive in the solid state as well. The chiroptical properties of compound 12 in solution and in the solid state indicate a strong chiral perturbation provided by the α‐stereogenic centres, in spite of the stereodynamic nature of the [4]helicene flanking units.
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Dates et versions

hal-04286380 , version 1 (15-11-2023)

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Maurizio Mastropasqua Talamo, Thomas Cauchy, Francesco Zinna, Flavia Pop, Narcis Avarvari. Tuning the photophysical and chiroptical properties of [4]helicene‐diketopyrrolopyrroles. Chirality, 2023, 35 (11), pp.805-816. ⟨10.1002/chir.23593⟩. ⟨hal-04286380⟩
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