Crystal Engineering Using Polyiodide Halogen and Chalcogen Bonding to Isolate the Phenothiazinium Radical Cation and Its Rare Dimer, 10-(3-Phenothiazinylidene)phenothiazinium |
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Authors: | Andrew J. Peloquin Dr. Colin D. McMillen Dr. Scott T. Iacono Dr. William T. Pennington |
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Affiliation: | 1. Department of Chemistry, Clemson University, 219 Hunter Laboratories, Clemson, SC 29634-0973 USA;2. Department of Chemistry & Chemistry Research Center, Laboratories for Advanced Materials, US Air Force Academy, 2355 Fairchild Dr, Suite 2N255, Colorado Springs, CO 80840 USA |
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Abstract: | Utilizing facile one-electron oxidation of 10H-phenothiazine by molecular diiodine, the solid-state structure of the 10H-phenothiazinium radical cation was obtained in three cation:iodide ratios, as well as its THF and acetone solvates. Oxidation of 10H-phenothiazine with molecular diiodine in DMSO or DMF provided the structure of the radical coupling product 10-(3-phenothiazinyldene)phenothiazinium, which has not been crystallographically characterized to date. The radical cations were balanced by a mixture (I7)−, (I5)−, (I3)−, and I− anions, where a variety of chalcogen, halogen, and hydrogen bonding interactions stabilize the structures to reveal these interesting cationic species. |
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Keywords: | chalcogen bonding crystal engineering halogen bonding stacking interactions X-ray diffraction |
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