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Pacman and Hangman Metal Tetraazamacrocycles

Lee, Chang Hoon and Villágran, Dino and Cook, Timothy R. and Peters, Jonas C. and Nocera, Daniel G. (2013) Pacman and Hangman Metal Tetraazamacrocycles. ChemSusChem, 6 (8). pp. 1541-1544. ISSN 1864-5631.

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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.

Item Type:Article
Related URLs:
URLURL TypeDescription PublisherArticle
Peters, Jonas C.0000-0002-6610-4414
Nocera, Daniel G.0000-0001-5055-320X
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.
Group:CCI Solar Fuels
Funding AgencyGrant Number
Department of Energy (DOE)DE-FG02-05ER15745
NSF Center for Chemical Innovation Powering the PlanetCHE-0802907
Subject Keywords:cobalt; electrochemistry; homogeneous catalysis; hydrogen; palladium
Issue or Number:8
Record Number:CaltechAUTHORS:20131003-085853977
Persistent URL:
Official Citation:Lee, C. H., Villágran, D., Cook, T. R., Peters, J. C. and Nocera, D. G. (2013), Pacman and Hangman Metal Tetraazamacrocycles. ChemSusChem, 6: 1541–1544. doi: 10.1002/cssc.201300068
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:41649
Deposited By: Tony Diaz
Deposited On:03 Oct 2013 16:22
Last Modified:09 Mar 2020 13:19

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