In this study, the synthesis, characterization, optical properties and TD-DFT studies of 21 near infra-red (NIR) fluorophores, and cytotoxicity of selected four compounds are presented. Fluorophores have a chloroacrylic acid acceptor unit and various donor units such as indole, benzothiazole, benzo[e]indole, and quinoline. Further modifications are also done at the linker with t-butyl and phenyl groups. The fluorophores showed strong absorption in the NIR (700-970 nm) region due to their unique intramolecular charge transfer (ICT) between chloroacrylic acid and the donor moieties. The emission wavelength maxima of the fluorophores were between 798-870 nm. Compound 123 with quinoline donor moiety, showed an emission wavelength above 1000 nm. Time dependent density functional theory (TD-DFT) calculations showed that the charge transfer occurs from the donor groups to the acceptor chloroacrylic acid moiety. Fluorophores were also shown to possess a charge separation character.