Meso-Aryloxy and meso-arylaza linked BODIPY dimers: Synthesis, structures and properties

Abstract

meso-Aryloxy and meso-arylaza linked BODIPY dimers have been designed and synthesized by the nucleophilic aromatic substitution (SNAr) type reactions of phenylenediamines (a, b, c) and phenylenediols (d, e, f) with 8-chloro BODIPY. The photophysical and electrochemical properties of the BODIPY dimers were found to be dependent on the nature of the heteroatom at the meso position on the BODIPY ligand and the substitution pattern of the BODIPYs on the phenyl ring (i.e. ortho, meta and para). The experimental observations were supported by theoretical calculations. The single crystal X-ray structures of 1, 2b, 2c and 3e are reported. The packing diagram of 1 reveals a herringbone like structural arrangement, whereas 2b, 2c and 3e show complex 3D structural motifs. © 2014 the Partner Organisations.