1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2021

1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

Résumé

Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2 + 2] or a [4 + 2] Diels-Alder process. DFT calculations unraveled the mechanism of the [2 + 2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR and far-red/near-IR photoluminescence in the solid state up to 1550 nm.

Domaines

Chimie organique
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Origine : Publication financée par une institution

Dates et versions

hal-03157427 , version 1 (13-07-2021)

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Clotilde Philippe, Anh Thy Bui, Sabrinah Batsongo-Boulingui, Ziemowit Pokladek, Katarzyna Matczyszyn, et al.. 1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes. Organic Letters, 2021, 23 (6), pp.2007-2012. ⟨10.1021/acs.orglett.1c00136⟩. ⟨hal-03157427⟩
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