Extended styryl dyes based on 2-chloroimidazo[1,2-a]pyridine-3-carbaldehyde showed alarge bathochromic shift in the range between 399 to 416 nm from starting aldehydes in range of 300 to 333 nm. Hyperconjugated electron donating methyl group and alone pair of nitrogen are in proper resonance with electron acceptor styryl group. These methylated dyes displayed 6 to 8 nm enhancement in broad absorption maximum in various nine solvents. Computational absorption wavelengths trends are matching with the experimental trends. In HOMO-LUMO energy gap, methylated dyes showed a consistent decrease in the energy gap of 0.05 eV than nonmethylated dyes.Dyeswere studied using various solvent polarity scales and multilinear regression analysis using Kamlet-Taft and Catalan scales.NBO analysis, a large number of stabilization energy E(2) entries were observed higher than 20 k J/ mol in both dyes indicating sufficient delocalization in donor-acceptor sites. In this research work,dipole moment (μ), electronic polarizability (α), mean first hyperpolarizability (βo) and second hyperpolarizability (γ)are computed with its fundamental limits and intrinsic values using density functional theory method in conjunction with 6-31G(d) basis set and vibrational NLO properties with 6-311++g(d,p) basis set.The dyes have fundamental limits and intrinsic properties within Hamiltonian limits. The fundamental limits provide a figure of merit for studied extended styryl dyes for future optical applications.