Solvent-Minimized Synthesis of 4CzIPN and Related Organic Fluorophores via Ball Milling
Jamie A. Leitch, Harry R. Smallman, Duncan L. Browne
Abstract
The mechanochemical synthesis of 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile and related organic fluorophores/photocatalysts via a solvent-minimized four-fold SNAr pathway is herein described. Employing sodium tert-butoxide as base, and negating the need for any air/moisture-sensitive reaction set-ups, a selection of organic dyes was synthesized in just 1 h using this ball-milling technique. Furthermore, the transformation was then showcased on a multigram scale.
Topics & Concepts
Ball millSolventOrganic synthesisOrganic solventChemistryNucleophilic aromatic substitutionBase (topology)MechanochemistryBall (mathematics)Organic chemistryChemical engineeringCombinatorial chemistryMaterials scienceNucleophilic substitutionCatalysisMathematicsEngineeringMathematical analysisLuminescence and Fluorescent MaterialsRadical Photochemical ReactionsCrystallography and molecular interactions