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N‐Arylation of Diketopyrrolopyrroles with Aryl Triflates
Author(s) -
Gutkowski Krzysztof,
Skonieczny Kamil,
Bugaj Marta,
Jacquemin Denis,
Gryko Daniel T.
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202000129
Subject(s) - aryl , anthracene , naphthalene , chemistry , excited state , coumarin , photochemistry , combinatorial chemistry , polar effect , absorption (acoustics) , phenols , computational chemistry , organic chemistry , materials science , atomic physics , composite material , alkyl , physics
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.