The synthesis, characterization, photophysical and mesomorphism of new hydrogen bonded (H-bonded) bent shaped mesogens derived from 1, 5-bis (4-hydroxyphenyl) penta-1, 4-dien-3-one are reported. The H-bonded bent shaped mesogens are formed by the complexation of 1: 2 molar ratio of 1, 5-bis (4-hydroxyphenyl) penta-1, 4-dien-3-one as bending unit and polar nitrile terminated ligands containing different linking groups (viz., imine (CHN), azo (NN), ester (COO)) as side wing. The transition temperatures and phase characterization have been investigated by differential scanning calorimetry and polarized optical microscopy. The bent core unit is fluorescent and non-mesogenic, whereas, all the nitrile terminated polar ligands are non-fluorescent and displayed enantiotropic smectic A phase. The H-bonded complexes are fluorescent and mesogenic. Nematic phase is induced in two H-bonded complexes whereas one of the H-bonded complexes displayed unidentified Bx phase. The computation studies are performed to obtain optimized stable molecular structures of the compounds, to investigate their electronic transitions and compared with experimental results.