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Published August 2013 | public
Journal Article

Pacman and Hangman Metal Tetraazamacrocycles

Abstract

Metal complexes of derivatized 2,12-dimethyl-3,7,11,17-tetraazabicyclo[11.3.1]heptadeca-1(17),2,11,13,15-pentane (bapa) ligands were prepared from 4-substituted diacetylpyridine derivatives by templated condensation with 3,3′-diaminodipropylamine in the presence of a metal halide or nitrate. The diacetylpyridine derivatives with Pacman and Hangman scaffolds are delivered from borylation of the 4-postion of diacetylpyridine and subsequent Suzuki coupling with the appropriate Hangman or Pacman backbone. Electrochemical examination of the parent [Co(bapa)]^(2+) scaffold reveals it to be a catalyst for the hydrogen evolution reaction (HER) in acetonitrile. Similar studies of the Hangman complex appear to be obscured by trace amounts of residual palladium remaining from the Suzuki coupling reaction to provide a cautionary note for the use of such cross-coupling methodologies in the preparation of HER catalysts.

Additional Information

© 2013 Wiley-VCH Verlag GmbH& Co. KGaA, Weinheim. Received: January 21, 2013; Revised: April 11, 2013; Published online on July 26, 2013. This research was supported by DOE grant DE-FG02-05ER15745 (D.G.N.) and the NSF Center for Chemical Innovation: Powering the Planet CHE-0802907 (J.C.P.). We thank Prof. M. Dinča for SEM and EDX analysis.

Additional details

Created:
August 22, 2023
Modified:
October 24, 2023