Highly soluble perylene diimide derivatives with symmetrical and unsymmetrical secondary, tertiary alkyl side chains were synthesized and their photophysical properties, redox potentials and thermal stabilities were measured and compared with previously reported 1-pentylhexyl substituted swallow-tailed perylene diimide. Diasteroisomers of the novel, unsymmetrical swallow-tailed substituted perylene diimide compound could not be detected using low temperature NMR spectroscopy. The novel dyes were soluble in a range of organic solvents indicating potential for photo-electronic applications and photocatalytic reactions. Two dyes were not only soluble in organic solvents but also showed solubility in aqueous media as the hydrochloride salt, thus offering potential use in biological applications. (C) 2009 Elsevier Ltd. All rights reserved.