The paper describes the self-assembly and liquid crystalline properties of pentadecylphenol tagged L-tryptophan molecules having ester and amide functionality. We have synthesized a series of molecules having mono and ditryptophan moieties attached to pentadecylphenol through amide or ester linkage. The fluorescence properties of the Boc-L-tryptophan-pentadecylphenol molecules were measured in methanol and found to aggregate beyond the critical aggregation concentration and self-assembled to give spherical structures. Upon deprotection of Boc group, the amine end group got involved in extended hydrogen bonding and fibril like structures were developed. These molecules also showed liquid crystalline behavior in hydrogen bonding solvents such as benzyl alcohol and showed needle like crystals in tert-butanol, as analyzed by polarized optical light microscopy.