Synthesis and characterization of lithium hemiporphyrazines

Inorganic Chemistry
Saovalak SripothongnakChristopher J Ziegler

Abstract

The hemiporphyrazines comprise a broad class of phthalocyanine analogues where one or two of the diiminoisoindolene units are replaced with alternative rings, including pyridines, benzenes, and azoles. As a means to explore the fundamental metal chemistry of these macrocycles, we have prepared the first lithium complexes of three hemiporphyrazine variants: the common bis-pyridine ring, the bis-benzene macrocycle (also known as dicarbahemiporphyrazine), and the monobenzene variant (also known as benziphthalocyanine). The metal cation can be inserted via reaction of the free bases by using lithium bis(trimethylsilyl)amide, and the resulting products all form 1:1 complexes with protonation at the meso nitrogens providing charge balance. For the two carbahemiporphyrazines studied, the internal C-H bond remains intact upon metalation. Similar structures have been observed in the transition metal complexes of the carbaporphyrins. In addition, all three complexes are characterized by (7)Li solid state NMR and by cyclic voltammetry.

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Citations

Jun 19, 2012·Inorganic Chemistry·Sabrina M HuberNathan W Luedtke
Jul 21, 2009·Chemical Communications : Chem Comm·Saovalak SripothongnakChristopher J Ziegler
Aug 30, 2014·The Journal of Physical Chemistry. a·Gabriel MarchandDenis Jacquemin
Sep 23, 2016·Chemical Reviews·Timothy D Lash
Sep 27, 2018·Angewandte Chemie·Wei ZhengJing-Lin Zuo
Feb 12, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Emily S BonnerChristopher J Ziegler
Nov 12, 2010·Chemical Communications : Chem Comm·Kimberly B FieldsChristopher J Ziegler
Jul 7, 2011·Chemistry : a European Journal·Margret M MeinholzDietmar Stalke
May 29, 2020·Chemical Communications : Chem Comm·Briana R SchrageChristopher J Ziegler
Nov 18, 2010·Chemical Communications : Chem Comm·Roshinee Costa, Christopher J Ziegler
May 31, 2013·Angewandte Chemie·Zhongrui ChenOlivier Siri
Jun 28, 2016·Chemistry, an Asian Journal·Yanping WuZhen Shen
Oct 12, 2016·Chemistry : a European Journal·Zhongrui ChenOlivier Siri
Jun 1, 2010·Inorganic Chemistry·Saovalak Sripothongnak, Christopher J Ziegler
Dec 24, 2010·Chemical Reviews·John Mack, Nagao Kobayashi
Dec 19, 2016·Inorganic Chemistry·Allen J OsinskiChristopher J Ziegler

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