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

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Abstract

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 P21. 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.

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Data Availability

Crystallographic data for structure FDEABA reported in this paper has been deposited with the Cambridge Crystallographic Data Center, CCDC No. 940431. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, fax: +44 1223 336 033, E-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk.

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Acknowledgements

Authors thank the Central Instrumentation Facility, Pondicherry University for extending the instrumentation facilities.

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Authors and Affiliations

  1. Department of Physics, Srimad Andavan Arts and Science College (Autonomous), Affiliated to Bharathidasan University, Tiruchirappalli, Tamil Nadu, 620005, India

    A. Subashini

  2. Crystal Growth and Thin Film Laboratory, Department of Physics, Bharathidasan University, Tiruchirappalli, Tamil Nadu, 620024, India

    A. Subashini, K. Ramamurthi & R. Ramesh Babu

  3. Ultrafast and Nonlinear Optics Laboratory Raman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore, 560 080, India

    Reji Philip

  4. Institute of Physics, University of Neuchâtel, Rue Emile-Argand 11, Neuchâtel, 2000, Switzerland

    Helen Stoeckli-Evans

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  1. A. Subashini
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  2. Reji Philip
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  4. K. Ramamurthi
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  5. R. Ramesh Babu
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Contributions

All authors have contributed to the preparation of the manuscript. AS: Conceptualization, methodology and writing of original draft of the manuscript. RP: Z scan measurement. HSE: Crystal structure determination. RR and KR: Supervision and approval of the final version of the manuscript.

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Correspondence to A. Subashini or K. Ramamurthi.

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Supplementary material 1 (JPG 414.0 kb)

Proton NMR spectrum of FDEABA.

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Subashini, A., Philip, R., Stoeckli-Evans, H. et al. Crystal Structure, Hirshfeld Analyses, Spectral, Thermal, Two-Photon Absorption Properties and Optical Limiting Applications of Novel 4-Fluoro-N-[4-(diethylamino)benzylidene]aniline (FDEABA). J Chem Crystallogr 53, 370–378 (2023). https://doi.org/10.1007/s10870-022-00975-9

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