Synthesis, characterization of two new bicyclic oxazolidines and investigation of their optoelectronic properties using density functional theory

This paper presents a facile synthetic route to synthesise two new bicyclic oxazolidine compounds 3,5-bis(4- chlorophenyl)-7a-methyldihydro-1H-[1,3]oxazolo[3,4-c][1,3] oxazole (1) and 3,5-bis(2-methoxyphenyl)-7a-methyldihydro- 1H-[1,3]oxazolo[3,4-c][1,3]oxazole (2). The condensation reaction between 2-amino-2-methylpropane-1, 3-diol (ampdH2) and choloro- and methoxy- substituted aromatic aldehyde yielded the heterocyclic bicyclic compounds (1) and (2), respectively. The compounds are characterised by FT-IR and 1HNMR spectroscopy and structures are conclusively determined by single crystal X-ray diffraction analysis. The ground state geometries are optimised by using density functional theory (DFT) at B3LYP/6-31G** level of theory to compare the geometric parameters (bond lengths, bond angles and torsion angles) with the X-ray crystallographic data. The computed geometric parameters are in good agreement with the experimental data. To shed light on the electronic and photophysical properties, DFT/B3LYP/6-31G** and time dependent DFT have been applied, respectively. Intra-molecular charge transfer has been observed in both the compounds. The absorption wavelengths are calculated with and without the solvent (acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide and methanol) at TD-B3LYP/6-31G** level of theory.