Abstract Boron dipyrromethenes (BODIPYs) with bulky triphenylsilylphenyl (ethynyl) and triphenylsilylphenyl substituents on pyrrole sites were prepared via Hagihara–Sonogashira and Suzuki–Miyaura cross-coupling with ethynyl-terminated tetraphenylsilane and boronic acid-terminated tetraphenylsilane. The chromophores are designed to prevent intermolecular π–π stacking interaction and enhance fluorescence in the solid state. ...