Two novel bay-region chlorine- or phenoxy-substituted perylene tetracarboxylic tetrapropargylesters (PTTEs) and a phenoxy-substituted perylene monoimide dipropargylester (PMIDE) were synthesized, photophysically characterized, and decorated with energy donating coumarin chromophores by means of microwave-assisted Cu(I)-catalyzed 1,3-dipolar cycloaddition reactions.