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Paper | Regular issue | Vol 98, No. 12, 2019, pp.1707-1724
Published online, 7th January, 2020
DOI: 10.3987/COM-19-14184
Synthesis, Characterization, and Electronic and Structural Calculations of Some 1,4-Disubstituted Cyclopenta[d][1,2]oxazines

Nathan C. Tice,* Steven Wild, Christian Olmstead, Edwin D. Stevens, Bangbo Yan, Hannah Brooks, and Judith L. Jenkins

*Department of Physical Sciences, The University of Findlay, 1000 North Main Street, Findlay, OH 45840, U.S.A.

Abstract

Our current work focuses upon the formation and characterization of some 1,4-disubstituted cyclopenta[d][1,2]oxazines via ring closure with hydroxyl amine on a 1,2-diacyl cyclopentadiene precursor. Recently, we formed and characterized two fused-ring disubstituted oxazines (R = thienyl, 4-chlorophenyl) in high yield, which serve as precursors towards oxazine-based conducting polymers. X-ray crystallographic analysis of the thienyl oxazine did show favorable π-π stacking, critical to effective intermolecular charge transfer. To further evaluate its electronic and optical properties, theoretical calculations were performed on the thienyl oxazine, including Natural Bond Orbital analysis. Calculated values suggest a strong potential for Non-Linear Optical applications.