Synthesis, Structure, and Physicochemical Properties of Electron Donor-Acceptor Conjugates Based on Porphyrinoids and Tetracyanobuta-1,3-Diene

As result of their synthetic versatility and unique physical features, porphyrinoids have been widely utilized as building blocks for the preparation of molecular and supramolecular electron donor-acceptor (D-A) ensembles in which photoinduced energy/electron transfer events can be triggered/modulated as a function of the electronic character of the macrocycles’ counterpart(s). In this talk, after a general introduction about porphyrinoids and their use in optoelectronic applications, I will present some examples from our group on the preparation and study of phthalocyanine-,[1] subphthalocyanine-,[2] and subporphyrin-[3] based D-A systems in which the porphyrinoid has been connected to tetracyanobuta-1,3-diene, a molecular fragment with unique structural and electronic features (Figure 1a-c). References Sekita, M.; Ballesteros, B.; Diederich, F.; Guldi, D. M.; Bottari, G.; Torres, T. Angew. Chem. Int. Ed. 2016 , 55 , 5560. a) Winterfeld, K. A.; Lavarda, G.; Guilleme, J.; Sekita, M.; Guldi, D. M.; Torres, T.; Bottari, G. J. Am. Chem. Soc. 2017 , 139 , 5520; b) Winterfeld, K. A.; Lavarda, G.; Guilleme, J.; Guldi, D. M.; Torres, T.; Bottari, G. Chem. Sci. , 2019 , 10 , 10997; c) Lavarda, G.; Bhattacharjee, N.; Brancato, G.; Torres, T.; Bottari, G. Angew. Chem. Int. Ed. , 2020 , 59 , 21224; d) Esteso, V.; Caliò, L.; Espinós, H.; Lavarda, G.; Torres, T.; Feist, J.; García-Vidal, F. J.; Bottari, G.; Míguez, H. Solar RRL , 2021 , 5 , 2100308. Winterfeld, K. A.; Lavarda, G.; Yoshida, K.; Bayerlein, M. J.; Kise, K.; Tanaka, T.; Osuka, A.; Guldi, D. M.; Torres, T.; Bottari, G. J. Am. Chem. Soc. 2020 , 142 , 7920. Figure 1