Four component domino reaction for the synthesis of highly functionalized dimeric tetracyclic dilactam fluorophores: H-bond aided self-assembly

Abstract

A series of new dimeric tetracyclic dilactam fluorophores (DTDF) consisting of diazabicyclooctane-dione (DBOD) fused to tetrahydronaphthalene (THP) was designed and synthesized from a simple precursor. The monomers showed enhanced emission in THF–water solvent and also benzene-dimer like absorption and fluorescence, originating from the hydrogen-bonding aided self-assembly of dilactams. The crystal structures revealed water-mediated molecular aggregates with several hydrogen-bond bridges formed by water.