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Near‐IR Absorbing Nickel(II) Porphyrinoids Prepared by Regioselective Insertion of Silylenes into Antiaromatic Nickel(II) Norcorrole
Author(s) -
Fukuoka Takaki,
Uchida Kenya,
Sung Young Mo,
Shin JiYoung,
Ishida Shintaro,
Lim Jong Min,
Hiroto Satoru,
Furukawa Ko,
Kim Dongho,
Iwamoto Takeaki,
Shinokubo Hiroshi
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201309921
Subject(s) - antiaromaticity , silylene , nickel , regioselectivity , chemistry , ring (chemistry) , photochemistry , silicon , aromaticity , organic chemistry , molecule , catalysis
The treatment of an antiaromatic norcorrole Ni II complex with a kinetically stabilized silylene provided ring‐expansion products in excellent yields through the highly regio‐ and stereoselective insertion into the β‐β pyrrolic CC bonds. The resultant Ni II porphyrinoid monoinsertion product exhibited relatively strong near‐IR absorption bands due to the small HOMO–LUMO gap in spite of the disrupted cyclic π‐conjugation by the silicon atom.