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

submitted on 28.12.2020, 13:36 and posted on 29.12.2020, 08:34 by Clotilde Philippe, Anh Thy Bui, Sabrinah Batsongo-Boulingui, ziemowit Pokladek, Katarzyna Matczyszyn, Olivier Mongin, Loïc Lemiègre, Frédéric Paul, Trevor Hamlin, Yann Trolez

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.


ANR 17-CE07- 0038-01

PHC Polonium 37629XG

ARED Fluotet

SAD Fluosad


Email Address of Submitting Author


Univ Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR – UMR6226



ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest