Five new organic sensitizers of type Donor-π-Acceptor (D-π-A) were designed and synthesized to investigate the effect of anchoring mode and conjugation length towards TiO2 film which leads to influence the efficiency of the fabricated dye sensitized solar cells. These dyes were synthesized based on the triphenylamine as electron donor, a series aromatic amine as π-conjugated spacers and anchoring/acceptor groups. The optical absorption of sensitizers shows red shift as well as high molar extinction co-efficient with extension of the π-conjugation. The DSSC based on AD series show power conversion efficiency (PCE = η) ranging from 1.53 – 6.89 % under simulated AM 1.5 G. DSSCs based on AD4 and AD5 produce maximum IPCE of 74.8% and 71.9%, respectively while those based on AD1 and AD5 in particular produce maximum IPCE below 50%. This variation is due to an increase in conjugation and the number of anchoring groups. The short circuit current (Jsc), open circuit voltage (Voc), field factor (FF), and quantum efficiency (ƞ) also increased with increase in IPCE values. High Jsc values signified high electron collecting efficiencies, which in turn denote faster electron diffusion rates. Additionally, a rise in the value of the Voc might raise the life time of the DSSC. The PCE (ƞ) values of AD dyes especially those of AD4 and AD5 (ƞ = 6.86% and 6.89% respectively) were seen to be higher than those of some triphenylamine based DSSCs (SD series with elongated thiophen units) whose PCE values ranged from 1.91% to 3.92%.