Synthesis of a Neo-Confused Octaphyrin and the Formation of Its Mononuclear Complexes

Kai Zhang; Junda Zhang; Xin Li; Rui Guo; Hans Ågren; Zhongping Ou; Masatoshi Ishida; Hiroyuki Furuta; Yongshu Xie

doi:10.1021/acs.orglett.5b02363

Synthesis of a Neo-Confused Octaphyrin and the Formation of Its Mononuclear Complexes

Org Lett. 2015 Oct 2;17(19):4806-9. doi: 10.1021/acs.orglett.5b02363.

Authors

Kai Zhang¹, Junda Zhang¹, Xin Li², Rui Guo³, Hans Ågren², Zhongping Ou³, Masatoshi Ishida⁴, Hiroyuki Furuta⁴, Yongshu Xie¹

Affiliations

¹ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology , Shanghai 200237, P. R. China.
² Department of Theoretical Chemistry and Biology, School of Biotechnology, KTH Royal Institute of Technology , Stockholm Se-10691, Sweden.
³ School of Chemistry & Chemical Engineering, Jiangsu University , Zhenjiang 212013, P. R. China.
⁴ Center for Molecular Systems, Department of Chemistry and Biochemistry, Graduate School of Engineering, Education Center for Global Leaders in Molecular Systems for Devices, Kyushu University , Fukuoka 819-0395, Japan.

PMID: 26368594
DOI: 10.1021/acs.orglett.5b02363

Abstract

Novel neo-confused octaphyrin(1.1.1.1.1.1.1.0) (1) was synthesized by oxidative ring closure of an octapyrrane bearing two terminal "confused" pyrroles. Crystal structures of its Zn(II) and Cu(II) complexes (2 and 3) show a figure-of-eight conformation with unique mononuclear coordination structures. Photophysical data and theoretical calculations suggest that the neo-confused octaphyrin 1 is a 34π electron conjugated species showing nonaromaticity. Coordination of copper and zinc ions results in the further narrowing of the HOMO-LUMO gaps.

Publication types

Research Support, Non-U.S. Gov't