Synthesis and electrochemical and theoretical studies of V-shaped donor−acceptor hexaazatriphenylene derivatives for second harmonic generation

8 páginas, 4 figuras, 3 tablas, 4 esquemas, 1 dibujo.-- et al.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.We thank Comunidad Autónoma de Madrid (project S2009/MAT-1467), Gobierno de Aragón-Fondo Social Europeo (Project E39), the UCM-BSCH joint project (GR58/08), and the MCyT of Spain (CTQ2007- 60459, CTQ2008-02942, CTQ2010-14982, MAT2008-06522-C02-02) for financial support. R.J. and R.A. are indebted to the “Universidad Rey Juan Carlos” and the Spanish Government (FPI program, No. BES2006-12104), respectively, for predoctoral fellowships.Peer reviewe