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A Radically Configurable Six-State Compound

By 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, III William A. Goddard and J. Fraser Stoddart

Abstract

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

Publisher: American Association for the Advancement of Science
Year: 2013
OAI identifier: oai:authors.library.caltech.edu:36816
Provided by: Caltech Authors

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