{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T21:50:37Z","timestamp":1791150637350,"version":"4.1.0"},"reference-count":76,"publisher":"American Chemical Society (ACS)","issue":"5","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Am. Chem. Soc."],"published-print":{"date-parts":[[2009,2,11]]},"DOI":"10.1021\/ja808465c","type":"journal-article","created":{"date-parts":[[2009,1,21]],"date-time":"2009-01-21T16:25:04Z","timestamp":1232555104000},"page":"1717-1723","source":"Crossref","is-referenced-by-count":86,"title":["Intramolecular Electron-Transfer Rates in Mixed-Valence Triarylamines: Measurement by Variable-Temperature ESR Spectroscopy and Comparison with Optical Data"],"prefix":"10.1021","volume":"131","author":[{"given":"Kelly","family":"Lancaster","sequence":"first","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Susan A.","family":"Odom","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simon C.","family":"Jones","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S.","family":"Thayumanavan","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Seth R.","family":"Marder","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean-Luc","family":"Br\u00e9das","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Veaceslav","family":"Coropceanu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen","family":"Barlow","sequence":"additional","affiliation":[{"name":"School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, and Department of Chemistry, University of Arizona, Tucson, Arizona 85721"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2009,1,21]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/S0065-2792(08)60179-X","volume":"10","author":"Robin M. B.","year":"1967","journal-title":"Adv. Inorg. Chem. Radiochem."},{"key":"ref2\/cit2","first-page":"391","volume":"8","author":"Hush N. S.","year":"1967","journal-title":"Prog. Inorg. Chem."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/0009-2614(95)01310-5","volume":"249","author":"Cave R. J.","year":"1996","journal-title":"Chem. Phys. Lett."},{"key":"ref4\/cit4","unstructured":"The dipole moment shift can be obtained from Stark-effect experiments or from quantum-mechanical calculations."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1002\/9780470166314.ch9","volume":"30","author":"Sutin N.","year":"1983","journal-title":"Prog. Inorg. Chem."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1080\/02603598508079692","volume":"3","author":"Richardson D. E.","year":"1985","journal-title":"Comments Inorg. Chem."},{"key":"ref7\/cit7","first-page":"6836","volume":"119","author":"Nelsen S. F.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"10213","DOI":"10.1021\/ja9720321","volume":"119","author":"Nelsen S. F.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"6873","DOI":"10.1021\/ja9634177","volume":"119","author":"Nelsen S. F.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"1388","DOI":"10.1021\/ja00030a038","volume":"114","author":"Rak S. F.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"2106","DOI":"10.1002\/anie.199421061","volume":"33","author":"Bonvoisin J.","year":"1994","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"846","DOI":"10.1126\/science.278.5339.846","volume":"278","author":"Nelsen S. F.","year":"1997","journal-title":"Science"},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"843","DOI":"10.1021\/ja011579j","volume":"124","author":"Lindeman S. V.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"2283","DOI":"10.1021\/jp012634d","volume":"106","author":"Rosokha S. V.","year":"2002","journal-title":"J. Phys. Chem. A"},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"1388","DOI":"10.1021\/ja038746v","volume":"126","author":"Sun D.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1002\/1521-3765(20010105)7:1<240::AID-CHEM240>3.0.CO;2-H","volume":"7","author":"Rovira C.","year":"2001","journal-title":"Chem. Eur. J."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1063\/1.98799","volume":"51","author":"Tang C. W.","year":"1987","journal-title":"Appl. Phys. Lett."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1038\/380029a0","volume":"380","author":"Bulovic V.","year":"1996","journal-title":"Nature"},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"1332","DOI":"10.1126\/science.267.5202.1332","volume":"267","author":"Kido J.","year":"1995","journal-title":"Science"},{"key":"ref20\/cit20","volume-title":"Organic Photoreceptors for Xerography","author":"Borsenberger P. M.","year":"1998"},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"5052","DOI":"10.1021\/j100070a018","volume":"98","author":"Bonvoisin J.","year":"1994","journal-title":"J. Phys. Chem."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"17079","DOI":"10.1021\/jp9610933","volume":"100","author":"Bonvoisin J.","year":"1996","journal-title":"J. Phys. Chem."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"2107","DOI":"10.1002\/(SICI)1521-3773(19980817)37:15<2107::AID-ANIE2107>3.0.CO;2-H","volume":"37","author":"Lambert C.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"2129","DOI":"10.1002\/(SICI)1521-3765(19981102)4:11<2129::AID-CHEM2129>3.0.CO;2-0","volume":"4","author":"Lambert C.","year":"1998","journal-title":"Chem. Eur. J."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"8434","DOI":"10.1021\/ja991264s","volume":"121","author":"Lambert C.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"7751","DOI":"10.1021\/jp004515o","volume":"105","author":"Lambert C.","year":"2001","journal-title":"J. Phys. Chem. A"},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1038\/nmat706","volume":"1","author":"Lambert C.","year":"2002","journal-title":"Nat. Mater."},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"3467","DOI":"10.1002\/1521-3765(20020802)8:15<3467::AID-CHEM3467>3.0.CO;2-1","volume":"8","author":"Lambert C.","year":"2002","journal-title":"Chem. Eur. J."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"10409","DOI":"10.1063\/1.1415747","volume":"115","author":"Coropceanu V.","year":"2001","journal-title":"J. Chem. Phys."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"10519","DOI":"10.1021\/ja026437j","volume":"124","author":"Coropceanu V.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1016\/S0009-2614(03)00553-0","volume":"373","author":"Coropceanu V.","year":"2003","journal-title":"Chem. Phys. Lett."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1002\/chem.200305200","volume":"10","author":"Low P. J.","year":"2004","journal-title":"Chem. Eur. J."},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"6474","DOI":"10.1021\/jp048449s","volume":"108","author":"Lambert C.","year":"2004","journal-title":"J. Phys. Chem. A"},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"7834","DOI":"10.1021\/ja0395386","volume":"126","author":"Szeghalmi A. V.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"11782","DOI":"10.1021\/ja045869m","volume":"126","author":"Jones S. C.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"8508","DOI":"10.1021\/ja0512172","volume":"127","author":"Lambert C.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"764","DOI":"10.1039\/B415018J","author":"Barlow S.","year":"2005","journal-title":"Chem. Commun."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"16900","DOI":"10.1021\/ja054136e","volume":"127","author":"Barlow S.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"238","DOI":"10.1002\/poc.1024","volume":"19","author":"N\u00f6ll G.","year":"2006","journal-title":"J. Phys. Org. Chem."},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"3197","DOI":"10.1021\/jp066681n","volume":"111","author":"N\u00f6ll G.","year":"2007","journal-title":"J. Phys. Chem. C"},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"1177","DOI":"10.1021\/jp0550309","volume":"110","author":"Amthor S.","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref42\/cit42","first-page":"3512","volume":"111","author":"N\u00f6ll G.","year":"2007","journal-title":"J. Phys. Chem."},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"3300","DOI":"10.1002\/anie.200603360","volume":"46","author":"Hirao Y.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref44\/cit44","unstructured":"Five-line spectra were observed at all temperatures, indicative of rapid ET; however, simulation of the temperature-dependent line shapes yielded ET rates. Although these data were interpreted using an Eyring plot, they can also be satisfactorily fit to an Arrhenius expression to give a prefactor of ca. 3 \u00d7 1012s\u22121and a barrier of 1300 cm\u22121."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"6231","DOI":"10.1021\/j100379a016","volume":"94","author":"Veregin R. P.","year":"1990","journal-title":"J. Phys. Chem."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"8223","DOI":"10.1021\/jp054401i","volume":"110","author":"Rohde D.","year":"2006","journal-title":"J. Phys. Chem. B"},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"9637","DOI":"10.1002\/chem.200700668","volume":"13","author":"Odom S. A.","year":"2007","journal-title":"Chem. Eur. J."},{"key":"ref48\/cit48","doi-asserted-by":"crossref","first-page":"1403","DOI":"10.1135\/cccc20001403","volume":"65","author":"F\u00e1ber R.","year":"2000","journal-title":"Collect. Czech. Chem. Commun."},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"9105","DOI":"10.1021\/ja050184n","volume":"127","author":"Yan X. Z.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref50\/cit50","doi-asserted-by":"crossref","first-page":"4998","DOI":"10.1039\/b711328e","volume":"17","author":"Rapta P.","year":"2007","journal-title":"J. Mater. Chem."},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"1585","DOI":"10.1016\/0040-4039(95)00094-S","volume":"36","author":"Stickley K. R.","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref52\/cit52","unstructured":"Since cyanoarenes are often poorly soluble in solvents such as CH2Cl2, compound7was synthesized with the electronically similar, but more solubilizing, BuO groups in place of the MeO groups used for compounds1\u22126."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1002\/cber.19580910113","volume":"91","author":"Horner L.","year":"1958","journal-title":"Chem. Ber."},{"key":"ref54\/cit54","doi-asserted-by":"crossref","first-page":"1733","DOI":"10.1021\/ja01468a042","volume":"83","author":"Wadsworth W. S.","year":"1961","journal-title":"J. Am. Chem. Soc."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"6853","DOI":"10.1021\/jp014675f","volume":"106","author":"Wenseleers W.","year":"2002","journal-title":"J. Phys. Chem. B."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"7215","DOI":"10.1021\/ja9608306","volume":"118","author":"Wolfe J. P.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"7217","DOI":"10.1021\/ja960937t","volume":"118","author":"Driver M. S.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref58\/cit58","doi-asserted-by":"crossref","first-page":"2727","DOI":"10.1021\/ja039263u","volume":"126","author":"Coropceanu V.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref59\/cit59","doi-asserted-by":"crossref","first-page":"1812","DOI":"10.1021\/ja0541534","volume":"128","author":"Zheng S.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"7959","DOI":"10.1021\/jp711954j","volume":"112","author":"Risko C.","year":"2008","journal-title":"J. Phys. Chem. C"},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"3498","DOI":"10.1021\/ja00967a006","volume":"88","author":"Seo E. T.","year":"1966","journal-title":"J. Am. Chem. Soc."},{"key":"ref62\/cit62","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1080\/00268977100102431","volume":"22","author":"Heinzer J.","year":"1971","journal-title":"Mol. Phys."},{"key":"ref63\/cit63","unstructured":"Heinzer, J.Quantum Chemistry Program Exchange,No. 209, 1972."},{"key":"ref64\/cit64","unstructured":"Although an Eyring analysis was used in ref11, the published VT-ESR data can also be fitted to an Arrhenius expression to give a barrier of 1130 cm\u22121, while a value of 1470 cm\u22121is obtained by analysis of the IVCT band, ifRis equated to the separation between the central carbons of the triarylmethyl groups."},{"key":"ref65\/cit65","unstructured":"In each case the IVCT band was satisfactorily fitted using a symmetrical Gaussian (with an additional variable offset included in the fit to model any non-zero baseline) over the energy range below which overlap with other transitions is evident, as previously reported for3+and related species(25, 27, 35, 38)and for6+. The neutral species, which are present in excess, do not absorb in the wavelength range shown in Figure5(seeSupporting Information), while the dications are, according to statistical considerations, present only at negligible concentrations. The estimated uncertainties in the transition dipole moments extracted from these spectra, taking into account both the uncertainty in the absorptivity measurement and the uncertainties in fitting the band, and in estimates ofVbased on these values of \u03bcgefor a givenR, are \u00b15%."},{"key":"ref66\/cit66","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1146\/annurev.pc.35.100184.002253","volume":"35","author":"Newton M. D.","year":"1984","journal-title":"Annu. Rev. Phys. Chem."},{"key":"ref67\/cit67","doi-asserted-by":"crossref","first-page":"2655","DOI":"10.1021\/cr990413m","volume":"101","author":"Demadis K. D.","year":"2001","journal-title":"Chem. Rev."},{"key":"ref68\/cit68","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1039\/b008034i","volume":"31","author":"Brunschwig B. S.","year":"2002","journal-title":"Chem. Soc. Rev."},{"key":"ref69\/cit69","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1007\/s00214-003-0445-3","volume":"110","author":"Coropceanu V.","year":"2003","journal-title":"Theor. Chem. Acc."},{"key":"ref70\/cit70","doi-asserted-by":"crossref","first-page":"17311","DOI":"10.1021\/j100048a004","volume":"99","author":"Horng M. L.","year":"1995","journal-title":"J. Phys. Chem."},{"key":"ref71\/cit71","doi-asserted-by":"crossref","first-page":"1518","DOI":"10.1021\/om9503712","volume":"15","author":"Pangborn A. B.","year":"1996","journal-title":"Organometallics"},{"key":"ref72\/cit72","doi-asserted-by":"crossref","first-page":"877","DOI":"10.1021\/cr940053x","volume":"96","author":"Connelly N. G.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref73\/cit73","unstructured":"For an overview of the self-interaction error, see:"},{"key":"ref73\/cit73a","volume-title":"A Chemist\u2019s Guide to Density Functional Theory","author":"Koch W.","year":"2002"},{"key":"ref74\/cit74","volume-title":"Gaussian 03","year":"2003"},{"key":"ref75\/cit75","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1006\/jmrb.1994.1062","volume":"104","author":"Duling D. R.","year":"1994","journal-title":"J. Magn. Reson. Ser. B"}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja808465c","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,3,9]],"date-time":"2024-03-09T09:29:56Z","timestamp":1709976596000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ja808465c"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,1,21]]},"references-count":76,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2009,2,11]]}},"alternative-id":["10.1021\/ja808465c"],"URL":"https:\/\/doi.org\/10.1021\/ja808465c","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,1,21]]}}}