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In this article we describe novel synthetic strategies toward well-defined disubstituted conjugated hexaazatriphenylene (HAT) derivatives. The systems are designed as novel V-shaped chromophores displaying C2 symmetry suitable for nonlinear optical investigations. Different donor moieties and linkers have been used in order to tune the electrochemical properties as well as the absorption spectra of the novel HAT derivatives. μβ values as high as 1010 × 10(-48) esu have been obtained for a derivative containing the electron-rich dibutylamino moiety. Theoretical calculations have been performed showing a reasonable agreement with the experimental results and supporting the two-dimensional NLO character of these chromophores.

Synthesis and Electrochemical and Theoretical Studies of V-Shaped Donor−Acceptor Hexaazatriphenylene Derivatives for Second Harmonic Generation