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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Crystal Engineering Using Polyiodide Halogen and Chalcogen Bonding to Isolate the Phenothiazinium Radical Cation and
Andrew J Peloquin1, Colin D McMillen1, Scott T Iacono2
1Department of Chemistry, Clemson University, 219 Hunter Laboratories, Clemson, SC 29634-0973, USA.
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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