Introduction of an azulene moiety to the porphyrinoid framework is of particular interest because of the unusual electronic properties of this bicyclic system. Exploration of this concept led to the synthesis of azuliporphyrin and its heteroanalogues - systems that exhibit borderline macrocyclic aromaticity and unusual reactivity pathways [1, 2].

The newly designed dithia- and dioxadiazuliporphyrins are nonaromatic porphyrinoids, easily oxidizable to their radical cations and, consequently, to the aromatic dications [3]. Combination of the azulene π system with the porphyrin-like macrocyclic framework results in a redox-switchable chromophore system with a potential for electrochromic and molecular conductivity applications.

[1] D. A. Colby, T. D. Lash, Chem. Eur. J. 2002, 8, 5397.

[2] S. Venkatraman, V. G. Anand, V. PrabhuRaja, H. Rath, J. Sankar, T. K. Chandrashekar, W. Teng, K. R. Senge, Chem. Commun. 2002, 1660.

[3] N. Sprutta, M. Świderska, L. Latos-Grażyński, J. Am. Chem. Soc. 2005, 127, 13108.

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1. 22-Hydroxybenziporphyrin: Switching of Antiaromaticity by Phenol-Keto Tautomerization
2. Carbaporphyrinoids: Exploring Metal Ion - Arene Interaction in a Macrocyclic Environment