Preparation of diverse BODIPY diesters

[Display omitted] •The synthesis and properties of a 6 different substituted BODIPY diesters is presented.•Examples provide points of attachment for biomolecules.•Combinatorial approach to dipyrrolemethane and BODIPY preparations gives access to many new scaffolds.•UV–Vis and fluorescent data adds to knowledge of this important fluorophore. The synthesis and properties of a variety of substituted BODIPY diesters is presented. We find that certain substitution patterns afford appreciable yields of the target compounds and that electronic effects result in predicable differential fluorescent behavior. Challenges to further water solubilize these dyes and/or provide new points of attachment for biological tagging remain, these strategies are discussed.