BODIPY dyes: Versatile building blocks to construct multiple types of self-assembled structures

Abstract

More than 50 years have passed since the discovery of boradiazaindacenes by Treibs and Kreuzer [Liebigs Ann. Chem. 718, 208 (1968)]. Since then, the number of research articles related to their synthesis, properties, and applications has not stopped growing. Not without reason, borondipyrromethene (BODIPY) dyes are one of the most versatile chromophores in terms of photophysical and chemical properties and multiple potential applications. For many applications, control over the properties in the aggregated state is necessary, and understanding the interactions that take part in the self-assembly of dye molecules is crucial. In this review, recent developments on the self-assembly of BODIPY dyes, as well as their potential applications, are discussed, highlighting the versatility of the BODIPY chromophore. In the first section, recent strategies to obtain solid-state emissive BODIPY dyes based on the introduction of different non-covalent interactions are presented. In a subsequent section, we discuss recent work on self-assembly and supramolecular polymerization of BODIPY dyes in aqueous and organic media with particular focus on pathway complexity—the analysis of different aggregation pathways by the same building block. In addition, given the high relevance of BODIPY dyes in biomedicine, a short overview of new BODIPY-based structures with interesting applications in biomedicine is presented. This section is followed by the discussion of recent work on metallosupramolecular assemblies of BODIPY dyes. Finally, a brief overview of other structurally related BODIPY-based analogs is given with particular focus on self-assembled structures of aza-BODIPY dyes.