The synthesis and physicochemical characterization of C-pivot hexadentate 5-[[3-[(8-hydroxy-5-quinolyl)methoxy]-2-[(8-hydroxy-5-quinolyl) methoxymethyl]-2-methylpropoxy]methyl]quinoline-8-ol (TMOM5OX) have been described. The tripod was built from a tetrahedral carbon as an anchor, symmetrically connected by three methoxymethane linkages, each bearing a terminal 8-hydroxyquinoline (8HQ). TMOM5OX was characterized by NMR, mass, infrared, and spectrophotometric techniques. The protonation equilibria and formation constant of different acidic forms of tripod were determinated by potentiometric, absorption and emission spectrophotometric methods. From the observed values, the distribution of the species as a function of the pH was then derived. Density functional theory with B3LYP functional and 6-311G* basis set was employed for optimization, vibrational modes, and excitation and emission properties of the protonated, neutral, and deprotonated states of the analogue. The photophysical properties of TMOM5OX in water was studied experimentally as well as by time-dependent density functional theory (TD-DFT). The observed anomalous enhancement in the fluorescence spectra of the cationic forms of TMOM5OX can be attributed to subtle structural differences from its neutral and anionic forms. The reduced fluorescent properties of the anionic form of TMOM5OX could be attributed to the competition of a nonradiative relaxation path.