To investigate the effect of hydrophobicity, charge and size of photosensitizers (PS) on their encapsulation efficiency in organically modified silica nanoparticles (ORMOSIL), a series of alkyl ether analogs of 2-(1'-hexyloxyethyl)-2-devinyl pyropheophorbide-a (HPPH) containing varied number of carbon units, HPPH with anionic and cationic functionalities, and HPPH analogs with molecular weight ranging from similar to 630 to 6000 Daltons were synthesized. Our preliminary results suggest that these factors play a significant role in encapsulation of the photosensitizers and their release from ORMOSIL nanoparticles. The synthesis and characterization of PS-encapsulated ORMOSIL and a comparative study on the effect of PS size, lipophilicity and charge on encapsulation efficiency, photophysical characteristics and release kinetics are discussed.