By combining the well-known motifs of BODIPY dyes and cycloparaphenylenes, novel nanohoop derivatives were accessible via established procedures. Absorption and emission spectra showed overall bathochromic shifts, and their photophysical behavior can be tuned by introducing steric demand to modulate the conjugation throughout the system. F NMR spectra underline distinct differences in the conformations, and (TD)DFT calculations provide a deeper insight into the geometry, photophysical behavior, and influence of steric demand.