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

Authors:

Ghulam Abbas,

Karlsruhe Institute of Technology, DE
About Ghulam
Institut für Anorganische Chemie
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Ahmad Irfan ,

King Khalid University, SA
About Ahmad
Research Center for Advanced Materials Science (RCAMS)
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Shahid Hameed,

Quaid-i-Azam University, PK
About Shahid
Department of Chemistry
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Abdullah G. Al-Sehemi,

King Khalid University, SA
About Abdullah G.
Research Center for Advanced Materials Science (RCAMS)
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Ruifa Jin,

Chifeng University, CN
About Ruifa
College of Chemistry and Chemical Engineering
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Shanshan Tang

Jilin Agriculture University, CN
About Shanshan
College of Life Science
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Abstract

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.

How to Cite: Abbas, G., Irfan, A., Hameed, S., Al-Sehemi, A.G., Jin, R. and Tang, S., 2018. Synthesis, characterization of two new bicyclic oxazolidines and investigation of their optoelectronic properties using density functional theory. Journal of the National Science Foundation of Sri Lanka, 46(2), pp.197–204. DOI: http://doi.org/10.4038/jnsfsr.v46i2.8420
Published on 30 Jun 2018.
Peer Reviewed

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