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Article Dans Une Revue Chemistry - An Asian Journal Année : 2020

N‐Arylation of Diketopyrrolopyrroles with Aryl Triflates

Krzysztof Gutkowski
Kamil Skonieczny
Marta Bugaj
  • Fonction : Auteur
Denis Jacquemin
Daniel Gryko

Résumé

A new methodology for the double N-arylation of diketopyrrolopyrroles with aryl triflates has been developed. It is now possible to prepare diketopyrrolopyrroles bearing N-substituents derived from naphthalene, anthracene and coumarin in two steps from commercially available phenols. This represents the first time arenes lacking strong electron-withdrawing groups were inserted onto lactamic nitrogen atoms via arylation. The ability to incorporate heretofore unprecedented substituents translates to increased modulation of the resulting photophysical properties such as switching-on/off solvatofluorochromism. TD-DFT calculations have been performed to explore the nature of the relevant excited states. This new synthetic method made it possible to elucidate the influence of such substituents on the absorption and emission properties of tetraaryl substituted diketopyrrolopyrroles

Domaines

Chimie
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Dates et versions

hal-03426255 , version 1 (12-11-2021)

Identifiants

Citer

Krzysztof Gutkowski, Kamil Skonieczny, Marta Bugaj, Denis Jacquemin, Daniel Gryko. N‐Arylation of Diketopyrrolopyrroles with Aryl Triflates. Chemistry - An Asian Journal, 2020, 15 (8), pp.1369-1375. ⟨10.1002/asia.202000129⟩. ⟨hal-03426255⟩
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