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

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]thiahelic...

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Published in:Chirality (New York, N.Y.) N.Y.), 2023-11, Vol.35 (11), p.805-816
Main Authors: Mastropasqua Talamo, Maurizio, Cauchy, Thomas, Zinna, Francesco, Pop, Flavia, Avarvari, Narcis
Format: Article
Language:English
Subjects:
Alkylation
Chemical Sciences
Chiral dynamics
Enantiomers
Nitrogen atoms
Perturbation
Solid state
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Summary: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.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23593