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