The synthesis of two [2.2]paracyclophane-based molecular systems with a pi -conjugated aromatic backbone have been reported and their utilization as active layer in organic solar cells was explored. Structure analysis based on extensive NMR investigation is reported too. The morphological and optical properties have been investigated by means of atomic force microscopy and UV-Vis spectroscopy. It was observed that the concomitant presence of the anthracene core and the amino group at the end of the side-chain reduces the film roughness with better light harvesting properties showing the highest open-circuit voltage and short-circuit current density. On the contrary no photovoltaic behaviour was observed when the amino group was absent. (c) 2008 Elsevier B.V. All rights reserved.