Four small dyes with triphenylamine (TPA) as a donor and various acceptor groups connected with π-linker having chloro group are synthesized and studied for solvatochromism and DFT. Good solvatochromism is observed in compounds 2 and 4 having TPA attached to rhodamine-3-acetic acid and 4-aminosalicylic acid. The multilinear regression analysis supports the solvatochromic behaviour of the chromophores. The compound 4 shows viscosity sensing with 0.57 viscosity sensitivity (x) value as which is more as compared with the other compounds, and 14.14-fold increased emission intensity in viscous solution from 0 to 99% of PEG-400 in ethanol. These TPA based compounds 1, 2, 3, and 4 show two-photon absorption cross section in the range 702-1265 GM. The natural bond analysis shows charge transfer in compound having strong withdrawing groups, that is compound 1 and 2. The bond length alteration is correlated with the computationally obtained NLO properties and show linear correlation. The compound 1 is a better NLOphoric material than the other compound 2, 3, and 4 as revealed by solvatochromic and computational methods.