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A Radically Configurable Six-State Compound


Jonathan C. Barnes, Albert C. Fahrenbach, Dennis Cao, Scott M. Dyar, Marco Frasconi, Marc A. Giesener, Diego Benítez, Ekaterina Tkatchouk, Oleksandr Chernyashevskyy, Weon Ho Shin, Hao Li, Srinivasan Sampath, Charlotte L. Stern, Amy A. Sarjeant, Karel J. Hartlieb, Zhichang Liu, Raanan Carmieli, Youssry Y. Botros, Jang Wook Choi, Alexandra M. Z. Slawin, John B. Ketterson, Michael R. Wasielewski, William A. Goddard III, J. Fraser Stoddart


 


Science
Vol. 339 no. 6118 pp. 429-433
DOI: 10.1126/science.1228429


 




Most organic radicals possess short lifetimes and quickly undergo dimerization or oxidation. Here, we report on the synthesis by radical templation of a class of air- and water-stable organic radicals, trapped within a homo[2]catenane composed of two rigid and fixed cyclobis(paraquat-p-phenylene) rings. The highly energetic octacationic homo[2]catenane, which is capable of accepting up to eight electrons, can be configured reversibly, both chemically and electrochemically, between each one of six experimentally accessible redox states (0, 2+, 4+, 6+, 7+, and 8+) from within the total of nine states evaluated by quantum mechanical methods. All six of the observable redox states have been identified by electrochemical techniques, three (4+, 6+, and 7+) have been characterized by x-ray crystallography, four (4+, 6+, 7+, and 8+) by electron paramagnetic resonance spectroscopy, one (7+) by superconducting quantum interference device magnetometry, and one (8+) by nuclear magnetic resonance spectroscopy. 


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