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; J. Fraser Stoddart

doi:10.1126/science.1228429

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. SlawinJohn B. Ketterson, Michael R. Wasielewski, William A. Goddard, J. Fraser Stoddart

Northwestern University

Research output: Contribution to journal › Article › peer-review

112 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	429-433
Number of pages	5
Journal	Science
Volume	339
Issue number	6118
DOIs	https://doi.org/10.1126/science.1228429
Publication status	Published - Jan 25 2013

ASJC Scopus subject areas

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Barnes, J. C., Fahrenbach, A. C., Cao, D., Dyar, S. M., Frasconi, M., Giesener, M. A., Benítez, D., Tkatchouk, E., Chernyashevskyy, O., Shin, W. H., Li, H., Sampath, S., Stern, C. L., Sarjeant, A. A., Hartlieb, K. J., Liu, Z., Carmieli, R., Botros, Y. Y., Choi, J. W., ... Stoddart, J. F. (2013). A radically configurable six-state compound. Science, 339(6118), 429-433. https://doi.org/10.1126/science.1228429

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

In: Science, Vol. 339, No. 6118, 25.01.2013, p. 429-433.

Research output: Contribution to journal › Article › peer-review

Barnes, JC, Fahrenbach, AC, Cao, D, Dyar, SM, Frasconi, M, Giesener, MA, Benítez, D, Tkatchouk, E, Chernyashevskyy, O, Shin, WH, Li, H, Sampath, S, Stern, CL, Sarjeant, AA, Hartlieb, KJ, Liu, Z, Carmieli, R, Botros, YY, Choi, JW, Slawin, AMZ, Ketterson, JB, Wasielewski, MR, Goddard, WA & Stoddart, JF 2013, 'A radically configurable six-state compound', Science, vol. 339, no. 6118, pp. 429-433. https://doi.org/10.1126/science.1228429

Barnes, Jonathan C. ; Fahrenbach, Albert C. ; Cao, Dennis ; Dyar, Scott M. ; Frasconi, Marco ; Giesener, Marc A. ; Benítez, Diego ; Tkatchouk, Ekaterina ; Chernyashevskyy, Oleksandr ; Shin, Weon Ho ; Li, Hao ; Sampath, Srinivasan ; Stern, Charlotte L. ; Sarjeant, Amy A. ; Hartlieb, Karel J. ; Liu, Zhichang ; Carmieli, Raanan ; Botros, Youssry Y. ; Choi, Jang Wook ; Slawin, Alexandra M.Z. ; Ketterson, John B. ; Wasielewski, Michael R. ; Goddard, William A. ; Stoddart, J. Fraser. / A radically configurable six-state compound. In: Science. 2013 ; Vol. 339, No. 6118. pp. 429-433.

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abstract = "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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