Herein, we report the synthesis of polyfunctional BODIPY building blocks suitable to be subjected to several reaction sequences with complete chemoselectivity, which allowed the preparation of complex BODIPY derivatives in a versatile and programmable manner. The reactions included: the Liebeskind-Srogl cross-coupling reaction (LSCC), S_NAr, Suzuki, Sonogashira, and Stille couplings and a desufitative reduction of the MeS- group. This novel synthetic protocol is a powerful route to design a library of compounds with tailored photophysical properties for advanced applications. In this context, it is noteworthy the straightforward and cost-less strategies to shift the BODIPY emission deep into the near infrared spectral region but retaining high fluorescence quantum yields.