Estimation of Ground-State and Singlet Excited-State Dipole Moments of Substituted Schiff Bases Containing Oxazolidin-2-one Moiety through Solvatochromic Methods
- Title
- Estimation of Ground-State and Singlet Excited-State Dipole Moments of Substituted Schiff Bases Containing Oxazolidin-2-one Moiety through Solvatochromic Methods
- Creator
- Kumari R.; Varghese A.; George L.
- Description
- Absorption and fluorescence studies on novel Schiff bases (E)-4-(4-(4-nitro benzylideneamino)benzyl)oxazolidin-2-one (NBOA) and (E)-4-(4-(4-chlorobenzylidene amino)benzyl)oxazolidin-2-one (CBOA) were recorded in a series of twelve solvents upon increasing polarity at room temperature. Large Stokes shift indicates bathochromic fluorescence band for both the molecules. The photoluminescence properties of Schiff bases containing electron withdrawing and donating substituents were analyzed. Intramolecular charge transfer behavior can be studied based on the influence of different substituents in Schiff bases. Changes in position and intensity of absorption and fluorescence spectra are responsible for the stabilization of singlet excited-states of Schiff base molecules with different substituents, in polar solvents. This is attributed to the Intramolecular charge transfer (ICT) mechanism. In case of electron donating (?Cl) substituent, ICT contributes largely to positive solvatochromism when compared to electron withdrawing (?NO2) substituent. Ground-state and singlet excited-state dipole moments of NBOA and CBOA were calculated experimentally using solvent polarity function approaches given by LippertMataga, Bakhshiev, Kawskii-Chamma-Viallet and Reichardt. Due to considerable ?- electron density redistribution, singlet excited-state dipole moment was found to be greater than ground-state dipole moment. Ground-state dipole moment value which was determined by quantum chemical method was used to estimate excited-state dipole moment using solvatochromic correlations. Kamlet-Abboud-Taft and Catalan multiple linear regression approaches were used to study non-specific solute-solvent interaction and hydrogen bonding interactions in detail. Optimized geometry and HOMO-LUMO energies of NBOA and CBOA have been determined by DFT and TD-DFT/PCM (B3LYP/6-311G (d, p)). Mulliken charges and molecular electrostatic potential have also been evaluated from DFT calculations. 2016, Springer Science+Business Media New York.
- Source
- Journal of Fluorescence, Vol-27, No. 1, pp. 151-165.
- Date
- 2017-01-01
- Publisher
- Springer New York LLC
- Subject
- ETN; Ground and excited state dipole moments; Kamlet and Catalan parameters; Solvatochromic method; Stokes shift
- Coverage
- Kumari R., Department of Chemistry, Christ University, Bengaluru, 560 029, India; Varghese A., Department of Chemistry, Christ University, Bengaluru, 560 029, India; George L., Department of Chemistry, Christ University, Bengaluru, 560 029, India
- Rights
- Restricted Access
- Relation
- ISSN: 10530509; PubMed ID: 27704234; CODEN: JOFLE
- Format
- Online
- Language
- English
- Type
- Article
Collection
Citation
Kumari R.; Varghese A.; George L., “Estimation of Ground-State and Singlet Excited-State Dipole Moments of Substituted Schiff Bases Containing Oxazolidin-2-one Moiety through Solvatochromic Methods,” CHRIST (Deemed To Be University) Institutional Repository, accessed February 24, 2025, https://archives.christuniversity.in/items/show/17185.