title: Macrocyclic Transformations from Norrole to Isonorrole and an N-Confused Corrole with a Fused Hexacyclic Ring System Triggered by a Pyrrole Substituent.
abstract: Three kinds of fused porphyrinoids, L2-L4, possessing different types of corrole-based frameworks were synthesized from a pyrrole-substituted corrole isomer (norrole L1). Oxidation of L1 afforded a unique N-Cmeso -fused pyrrolyl isonorrole L2, involving the fusion of an auxiliary pyrrolic NH moiety with a meso-sp(3) -hybridized carbon atom. Subsequently, L2 underwent macrocycle transformations to give singly and doubly N-CAr -fused N-confused corroles, L3 and L4, respectively. L3 and L4 contain fused [5.7.6.5]-tetra- and [5.6.7.7.6.5]-hexacyclic structures, respectively, prepared through lateral annulation. These skeletal transformation reactions from norrole to its isomer isonorrole and finally to N-confused corrole indicate that multiply fused porphyrinoids could be readily synthesized from pyrrole-appended confused porphyrinoids.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, 200237, P.R. China.
authors.forename: Miao
authors.initials: M
authors.lastname: Li
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, 200237, P.R. China.
authors.forename: Pingchun
authors.initials: P
authors.lastname: Wei
authors.affiliation: Education Center for Global Leaders in Molecular Systems for Devices and Center for Molecular Systems, Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Ishida
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, 200237, P.R. China.
authors.forename: Xin
authors.initials: X
authors.lastname: Li
authors.affiliation: School of Chemistry, University of Manchester, Manchester, m139pl, UK.
authors.forename: Mathew
authors.initials: M
authors.lastname: Savage
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P.R. China.
authors.forename: Rui
authors.initials: R
authors.lastname: Guo
authors.affiliation: School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P.R. China.
authors.forename: Zhongping
authors.initials: Z
authors.lastname: Ou
authors.affiliation: School of Chemistry, University of Manchester, Manchester, m139pl, UK.
authors.forename: Sihai
authors.initials: S
authors.lastname: Yang
authors.affiliation: Education Center for Global Leaders in Molecular Systems for Devices and Center for Molecular Systems, Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan. hfuruta@cstf.kyushu-u.ac.jp.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Furuta
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai, 200237, P.R. China. yshxie@ecust.edu.cn.
authors.forename: Yongshu
authors.initials: Y
authors.lastname: Xie
keywords: N-confused corroles; aromaticity; corroles; fused-ring systems; porphyrinoids