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1,2,4,6-Thiatriazinyl Radicals and Dimers: Structural and Electronic Tuning through Heteroaromatic Substituent Modification

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posted on 06.05.2015, 00:00 by Nathan J. Yutronkie, Alicea A. Leitch, Ilia Korobkov, Jaclyn L. Brusso
The functionalization of thiatriazinyl (TTA) radicals with pyridyl and thienyl moieties is described, and their influence at both the molecular and solid-state level has been investigated. Comparative electron paramagnetic resonance studies of 3,5-bis-(2-pyridyl)-1,2,4,6-thiatriazinyl (Py2TTA) and 3,5-bis-(2-thienyl)-1,2,4,6-thiatriazinyl (Th2TTA) reveal the impact of heteroaromatic substitution on the electronic structure, which is supported by density functional theory calculations. Single crystal X-ray analysis emphasizes the importance of intermolecular contacts on the crystal packing and demonstrates the potential for structural control through S---N′ and N---HC′ interactions, which are enhanced in Py2TTA and Th2TTA by the presence of the pyridyl and thienyl groups, respectively. This work represents a fundamental study of heterocyclic aromatic substitution in thiazyl-based radicals and investigates how varying these functional groups influences the molecular properties and long-range order within the supramolecular structure.