Pyrazinacenes and Oxoporphyrinogens

Tuesday, 30 May 2017: 11:40
Churchill A2 (Hilton New Orleans Riverside)
J. P. Hill, D. Miklik, P. Svec (WPI Center for Materials Nanoarchitectonics), Y. Matsushita (National Institute for Materials Science), J. Labuta, S. Ishihara (WPI Center for Materials Nanoarchitectonics), F. D'Souza (University of North Texas), and K. Ariga (WPI Center for Materials Nanoarchitectonics)
Porphyrins substituted with antioxidant 2,6-di-tert-butylphenol substituents have been shown to exhibit different conformations based on the oxidation state of those substituents leading to the oxoporphyrinogens.1,2 On the other hand, pyrazinacenes are obtained by synthesis of linearly-fused 1,4-pyrazine groups giving molecules with potential as semiconductors, proton conductors or fluorescent labels. We have investigated both classes of compounds for their potential applications3,4 Here, we will describe the results of these investigations including highlighting the different compounds obtained from the porphyrin system, synthesis and structure in the phthalocyanine,5 TPA and HPB systems,6 and an extensive crystallographic analysis of the resorcinarene system.7 We will also present synthetic aspects of the pyrazinacene system including new synthesis pathways for higher derivatives.8 Finally, a molecular switch based on mechanical extension of an oxoporphyrinogen molecule will be described.9


(1) F. D’Souza, N. K. Subbaiyan, Y. Xie, J. P. Hill, K. Ariga, K. Ohkubo, S. Fukuzumi, J. Am. Chem. Soc. (2009) 131, 16138–16146. (2) J. P. Hill, I. J. Hewitt, C. E. Anson, A. K. Powell, A. L. McCarthy, P. Karr, M. Zandler, F. D’Souza, J. Org. Chem. (2004) 69, 5861–5869. (3) S. Ishihara, J. Labuta, T. Šikorský, J. V. Burda, N. Okamoto, H. Abe, K. Ariga, J. P. Hill, Chem. Commun. (2012) 48, 3933–3935 (4) A. Shundo, J. Labuta, J. P. Hill, S. Ishihara, K. Ariga, J. Am. Chem. Soc. (2009) 131, 9494–9495; J. Labuta, S. Ishihara, A. Shundo, S. Arai, S. Takeoka, K. Ariga, J. P. Hill, Chem. Eur. J. (2011) 17, 3558–3561. (5) J. P. Hill, N. K. Subbaiyan, F. D’Souza, Y. Xie, S. Sahu, N. M. Sanchez-Ballester, K. Ariga, Chem. Commun. (2012) 48, 3951–3953. (6) S. Jin, J. P. Hill, F. D'Souza, K. Ariga, (2016) in press. (7) D. Payne, J. P. Hill, F. D'Souza, K. Ariga, (2016) in press. (8) D. Miklik, P. Svec, J. P. Hill (2016) in press. (9) M. Perrin, J. P. Hill, D. Dulic, H. van der Zant, (2016) submitted.