We previously reported that constrained 2-phenylbenzo[b]phosphole P-oxides bearing a diphenylamino group show high photostability and thus are promising dyes for fluorescence imaging. Herein we investigated the impact of the bridging moieties on their photophysical properties. A series of benzo[b]phosphole P-oxides constrained with various carbon or silicon bridges were synthesized. All of these compounds showed significant solvatochromism in fluorescence due to the intramolecular charge-transfer character in the excited state. The dipole moments in the excited state for the carbon-bridged derivatives are slightly larger than the silicon-bridged counterparts. Nevertheless, the latter compounds showed orange-red fluorescence in polar solvents with ca. 30 nm red-shifted maxima compared to the carbon analogues. Most importantly, the assessment of their photobleaching resistance revealed that the photostability of this compound series highly relies on the steric bulkiness of the bridging moiety, and even the silicon-bridged derivative can show outstanding photostability, as far as the silicon-bridging moiety has sufficient bulkiness.