We have computationally designed and characterized a series of new organic D-pi-A architected dyes that have originated from cyanidin, which is vastly available in nature, for effective sensitization of DSSCs with absorption spectra extending up to near infrared region. Cyanidin acts as the donor group while cyanoacrylic acid and thieno [3, 2-b] thiophene are employed as the acceptor and pi-spacer, respectively. Sensitization performance, depending on the substituted position of the pi-spacer-acceptor (pi-A) combination on cyanidin molecule, is examined by the results of density functional theory (DFT) and time dependent density functional theory (TDDFT) calculations. The calculated data of free energy change driving force (Delta G(inject)), electron regeneration driving force (Delta G(regen)), open circuit potential eV(oc) and light harvesting efficiency (LHE) suggest two preferred substitutions of pi-A combination to cyanidin molecule that leads to an efficient DSSC. At LUMO the designed sensitizers have denser electron cloud towards acceptor group that leads to an efficient electron injection process. All pi-A substitutions resulted a broader absorption spectrum with a redshift up to 2500 nm which is a significant improvement compared to the vast majority of reported sensitizers.