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Oxidation of Electron Donor-Substituted Verdazyls: Building Blocks for Molecular Switches
Journal of Physical Chemistry A (2015)
  • Benjamin C. Haller, San Jose State University
  • Dallas Chambers, San Jose State University
  • Ran Cheng, San Jose State University
  • Victoria Chemistruck, San Jose State University
  • Timothy F. Hom, San Jose State University
  • Zhengzheng Li, San Jose State University
  • Jeffrey Nguyen, San Jose State University
  • Andrew Ichimura, San Francisco State University
  • David J R Brook, San Jose State University
Species that can undergo changes in electronic configuration as a result of an external stimulus such as pH or solvent polarity can play an important role in sensors, conducting polymers, and molecular switches. One way to achieve such structures is to couple two redox-active fragments, where the redox activity of one of them is strongly dependent upon environment. We report on two new verdazyls, one subsituted with a di-tert-butyl phenol group and the other with a dimethylaminophenyl group, that have the potential for such behavior upon oxidation. Oxidation of both verdazyls with copper(II) triflate in acetonitrile gives diamagnetic verdazylium ions characterized by NMR and UV–vis spectroscopies. Deprotonation of the phenol–verdazylium results in electron transfer and a switch from a singlet state to a paramagnetic triplet diradical identified by electron spin resonance. The dimethylaminoverdazylium 9 has a diamagnetic ground state, in line with predictions from simple empirical methods and supported by density functional theory calculations. These results indicate that verdazyls may complement nitroxides as spin carriers in the design of organic molecular electronics.
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Benjamin C. Haller, Dallas Chambers, Ran Cheng, Victoria Chemistruck, et al.. "Oxidation of Electron Donor-Substituted Verdazyls: Building Blocks for Molecular Switches" Journal of Physical Chemistry A Vol. 119 Iss. 43 (2015) p. 10750 - 10760 ISSN: 1089-5639
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