Synthesis and chiroptical properties of chiral azoaromatic dendrimers with a C3-symmetrical core

New chiral azoaromatic dendrimeric systems have been synthesized starting from 1,3,5-benzenetricarbonyl trichloride as core molecule. The simultaneous presence of the (S)-3-hydroxy pyrrolidinyl ring as optically active moiety and the azobenzene donor-acceptor conjugated system as photochromic group with permanent dipole moment, makes these systems potentially interesting as materials for advanced applications in nanotechnologies. All the obtained compounds have been characterized with a particular attention to the effects induced by changing the electron-withdrawing group in the chromophoric moiety and to their optical activity. A strong non-linear enhancement of the chiroptical properties related to the number of chiral units linked to the symmetrical core is observed in these derivatives, which indicates the presence of conformationally chiral substructures.