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 & 4 others John B. Ketterson, Michael R Wasielewski, William A. Goddard, J. Fraser Stoddart

Research output: Contribution to journalArticle

93 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 languageEnglish
Pages (from-to)429-433
Number of pages5
JournalScience
Volume339
Issue number6118
DOIs
Publication statusPublished - Jan 25 2013

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Oxidation-Reduction
Magnetometry
Electrochemical Techniques
Crystallography
Paraquat
Electron Spin Resonance Spectroscopy
Dimerization
Spectrum Analysis
Magnetic Resonance Spectroscopy
Air
X-Rays
Electrons
Equipment and Supplies
Water
catenane

ASJC Scopus subject areas

  • General

Cite this

Barnes, J. C., Fahrenbach, A. C., Cao, D., Dyar, S. M., Frasconi, M., Giesener, M. A., ... 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 journalArticle

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 JC, Fahrenbach AC, Cao D, Dyar SM, Frasconi M, Giesener MA et al. A radically configurable six-state compound. Science. 2013 Jan 25;339(6118):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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