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^*

^*Corresponding author for this work

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

139 Scopus citations

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

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10.1126/science.1228429

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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

@article{5bcd7b82e1ce429ea53d18731ba724ff,

title = "A radically configurable six-state compound",

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.",

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

year = "2013",

month = jan,

day = "25",

doi = "10.1126/science.1228429",

language = "English (US)",

volume = "339",

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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

TY - JOUR

T1 - A radically configurable six-state compound

AU - Barnes, Jonathan C.

AU - Fahrenbach, Albert C.

AU - Cao, Dennis

AU - Dyar, Scott M.

AU - Frasconi, Marco

AU - Giesener, Marc A.

AU - Benítez, Diego

AU - Tkatchouk, Ekaterina

AU - Chernyashevskyy, Oleksandr

AU - Shin, Weon Ho

AU - Li, Hao

AU - Sampath, Srinivasan

AU - Stern, Charlotte L.

AU - Sarjeant, Amy A.

AU - Hartlieb, Karel J.

AU - Liu, Zhichang

AU - Carmieli, Raanan

AU - Botros, Youssry Y.

AU - Choi, Jang Wook

AU - Slawin, Alexandra M.Z.

AU - Ketterson, John B.

AU - Wasielewski, Michael R.

AU - Goddard, William A.

AU - Stoddart, J. Fraser

PY - 2013/1/25

Y1 - 2013/1/25

N2 - 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.

AB - 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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UR - http://www.scopus.com/inward/citedby.url?scp=84872773951&partnerID=8YFLogxK

U2 - 10.1126/science.1228429

DO - 10.1126/science.1228429

M3 - Article

C2 - 23349286

AN - SCOPUS:84872773951

SN - 0036-8075

VL - 339

SP - 429

EP - 433

JO - Science

JF - Science

IS - 6118

ER -

A radically configurable six-state compound

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CCDC 889233: Experimental Crystal Structure Determination

CCDC 855030: Experimental Crystal Structure Determination

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A radically configurable six-state compound

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CCDC 855031: Experimental Crystal Structure Determination

CCDC 889233: Experimental Crystal Structure Determination

CCDC 855030: Experimental Crystal Structure Determination

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