Synthesis, crystal structure and photophysical properties of (E)-4-(4-(2-hydroxybenzylideneamino)benzyl)oxazolidin-2-one
- Title
- Synthesis, crystal structure and photophysical properties of (E)-4-(4-(2-hydroxybenzylideneamino)benzyl)oxazolidin-2-one
- Creator
- Kumari R.; Varghese A.; George L.
- Description
- A new Schiff base, (4-(benzylideneamino)benzyl)oxazolidin-2-one has been synthesised from 4-(4-aminobenzyl)oxazolidin-2-one and salicylaldehyde by a simple condensation reaction. Single-crystal X-ray analysis of (E)-4-(4-(2-hydroxybenzylideneamino) benzyl)oxazolidin-2-one (HBOA) revealed that there is a 1-D, slipped, face-to-face motif with off-set, head-to-tail stacked columns. Detailed studies on photophysical properties of the synthesised compound in solutions indicate their potential applications in the field of organic light emitting devices and nonlinear optical materials. Absorption and fluorescence study of HBOA has been conducted in a series of solvents with increasing polarity at room temperature. Ground and excited state dipole moments have been determined experimentally by using LippertMataga polarity function, Bakhshiev solvent polarity parameter, KawskiiChammaViallet solvent polarity parameter and Richardt?s microscopic solvent polarity parameter. Due to the considerable ?-electron density redistribution, the excited state dipole moment was found to be larger than that of the ground state. The ground state dipole moment value was determined by quantum chemical method which was used to estimate excited state dipole moment through solvatochromic correlations. KamletTaft and Catalan methods were used to get the information of both non-specific solutesolvent interactions and hydrogen bonding interactions. TD-DFT (B3LYP/6-311G(d,p)) has been used for the determination of HOMOLUMO energies. Mulliken charges and Molecular electrostatic potential were also evaluated from DFT calculations. 2016 Elsevier B.V.
- Source
- Journal of Luminescence, Vol-179, pp. 518-526.
- Date
- 2016-01-01
- Publisher
- Elsevier B.V.
- Subject
- Crystal packing; Ground and excited state dipole moment; Solvatochromic effect; Stokes shift
- Coverage
- Kumari R., Department of Chemistry, Christ University, Bangalore, 560029, India; Varghese A., Department of Chemistry, Christ University, Bangalore, 560029, India; George L., Department of Chemistry, Christ University, Bangalore, 560029, India
- Rights
- Restricted Access
- Relation
- ISSN: 222313; CODEN: JLUMA
- Format
- Online
- Language
- English
- Type
- Article
Collection
Citation
Kumari R.; Varghese A.; George L., “Synthesis, crystal structure and photophysical properties of (E)-4-(4-(2-hydroxybenzylideneamino)benzyl)oxazolidin-2-one,” CHRIST (Deemed To Be University) Institutional Repository, accessed February 22, 2025, https://archives.christuniversity.in/items/show/17172.