A new series of cyclometalated platinum(II) complexes of (NCN)-C-boolean AND-N-boolean AND ligands, where (NCN)-C-boolean AND-N-boolean AND = 1,3-bis(1-n-alkylpyrazol-3-yl)benzene (bpzb), namely, [Pt(bpzb)CI] (1 and 2) and [Pt(bpzb)(C C-R)] (3-10) (R = C6H5, C6H4-OCH3-p, C6H4 NO2-p, C6H4 NH2-p, 4-cholesteryl phenyl carbamate, and cholesteryl methylcarbamate) were synthesized and characterized. Their electrochemical and photophysical properties were investigated. Two of the platinum(II) complexes were also structurally characterized by X-ray crystallography, and short intermolecular C-H center dot center dot center dot Pt contacts were observed. Vibronic-structured emission bands originating from triplet IL (40 excited states of the bpzb ligands with mixing of some (MLCT)-M-3 [d pi(Pt))->pi*(bpzb)] character were observed in solution state. Interestingly, complex 5 shows a low energy emission that is derived from the involvement of the p-nitrophenylethynyl ligand. Complex 9 with hydrophobic cholesteryl 4-ethynylphenyl carbamate ligand was found to form stable metallogels in several organic solvents, which are responsive to mechanical sonication and thermal stimuli and show circular dichroism activity.