Encapsulation of Disperse red 1 (DR1) into the internal cavities of generation 4 and 5 of dimethylsilyl linked dihydroxybenzyl alcohol (DHBA) based dendrimers was investigated at various added concentrations of DR1, before and after aggregation, using UV-VIS absorption spectra. A blue shift in the lambda max (460nm) was observed upon encapsulation of DR1 as compared to lambda max of (485nm) for DR1. Simultaneously, calculations were performed using the robust PM3 Semi-empirical Molecular Orbital Theory to optimize the structures of 3,5 dihydroxybenzyl alcohol based dendrimers and obtain information related to the size and shape of the internal cavities, the electronic wavefunctions and the molecular energies of the dendrimers.