First Method for N-Arylation of Diketopyrrolopyrroles with Aryl Triflates.

08:00 EDT 10th March 2020 | BioPortfolio

Summary of "First Method for N-Arylation of Diketopyrrolopyrroles with Aryl Triflates."

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 has enabled the influence of such substituents on the absorption and emission properties of tetra-aryl substituted diketopyrrolopyrroles to be elucidated.


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This article was published in the following journal.

Name: Chemistry, an Asian journal
ISSN: 1861-471X


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