Crystal Structure, Hirshfeld Analyses, Spectral, Thermal, Two-Photon Absorption Properties and Optical Limiting Applications of Novel 4-Fluoro-N-[4-(diethylamino)benzylidene]aniline (FDEABA)

The novel third-order nonlinear optical organic material 4-fluoro- N -[4-(diethylamino)benzylidene]aniline (FDEABA) is synthesized and single crystals of FDEABA are grown using the slow evaporation method. The placement of the protons is confirmed by nuclear magnetic resonance spectral analysis. Emp...

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Bibliographic Details
Published in:Journal of chemical crystallography 2023-09, Vol.53 (3), p.370-378
Main Authors: Subashini, A., Philip, Reji, Stoeckli-Evans, Helen, Ramamurthi, K., Ramesh Babu, R.
Format: Article
Language:English
Subjects:
Aniline
Chemistry
Chemistry and Materials Science
Constraining
Crystal growth
Crystal structure
Crystallization
Crystallography and Scattering Methods
Differential thermal analysis
Fourier transforms
Functional groups
Infrared analysis
Inorganic Chemistry
Melting points
NMR
Nonlinear optics
Nuclear magnetic resonance
Optical properties
Organometallic Chemistry
Original Paper
Photon absorption
Physical Chemistry
Single crystals
Spectrum analysis
Stability analysis
Surface analysis (chemical)
Synthesis
Thermal stability
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Summary:The novel third-order nonlinear optical organic material 4-fluoro- N -[4-(diethylamino)benzylidene]aniline (FDEABA) is synthesized and single crystals of FDEABA are grown using the slow evaporation method. The placement of the protons is confirmed by nuclear magnetic resonance spectral analysis. Employing Fourier transform infrared spectral analysis, vibrational frequencies of various functional groups of the FDEABA compound are identified. The three-dimensional crystal structure of the grown crystal is elucidated using single crystal X-ray diffraction studies, which reveal that the compound FDEABA crystallized in the monoclinic non-centrosymmetric space group P2 1 . Intermolecular interactions are studied using Hirshfeld surface analysis and compared with similar structures of halogen-substituted benzylideneaniline derivatives. Thermal stability of FDEABA is measured using thermogravimetric and differential thermal analyses and the melting point of the synthesized FDEABA compound is 51 °C. Open aperture Z-scan measurements carried out at 532 nm using 5 ns laser pulses reveal nonlinear optical absorption leading to strong optical limiting behaviour, which can be useful in the protection of eyes and sensitive optical detectors from harmful laser radiation. Graphical Abstract
ISSN:1074-1542
1572-8854
DOI:10.1007/s10870-022-00975-9