Synthesis, characterization and unusual near-infrared luminescence of 1,1,4,4-tetracyanobutadiene derivatives
Anh Thy Bui, Clotilde Philippe, Maxime Beau, Nicolas Richy, Marie Cordier≈, Thierry Roisnel, Loı̈c Lemiègre, Olivier Mongin, Frédéric Paul, Yann Trolez
Abstract
Two 1,1,4,4-tetracyanobutadiene (TCBD) derivatives were prepared by [2+2]cycloaddition-retroelectrocyclization from ynamides bearing either a pyrene (1) or a perylene unit (2). In addition to panchromatic absorptions in 2, in the solid state, both compounds unexpectedly display NIR photoluminescence that could be detected up to about 1350 nm.
Topics & Concepts
PyrenePanchromatic filmLuminescencePhotoluminescencePeryleneSolid-stateCharacterization (materials science)InfraredChemistryPhotochemistryCycloadditionMaterials sciencePhysical chemistryOrganic chemistryMultispectral imageMoleculeNanotechnologyOptoelectronicsOpticsPhysicsComputer scienceCatalysisComputer visionCatalytic Alkyne ReactionsRadical Photochemical ReactionsClick Chemistry and Applications