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Tautomeric influence on the photoinduced birefringence of 4-substituted phthalimide 2-hydroxy Schiff bases in PMMA matrix

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Abstract

The photoinduced birefringence of two 4-substituted phthalimide 2-hydroxy Schiff bases, containing salicylic (4) and 2-hydroxy-1-naphthyl (5) moieties has been investigated in PMMA matrix. Their optical behaviour as nanocomposite films was revealed by combined use of DFT quantum chemical calculations (in ground and excited state) and experimental optical spectroscopy (UV–Vis and fluorescence). The results have shown that solid-state reversible switching takes place by enol/keto tautomerization and Z/E isomerization. Birefringence study was performed in the PMMA nanocomposite films using pump lasers at λrec = 355 nm and λrec = 442 nm. Fast response time and high stability of anisotropy up to 58% for (4) and 95% for (5) after turning off the excitation laser, was observed, which makes these materials appropriate candidates for cutting-edge optical information technology materials. The possibility for multiple cycles of recording, reading and optical erasure of the photoinduced birefringence at λrec = 442 nm in 5 has been demonstrated. The obtained results have shown that the maximum value of the measured birefringence is close to the anisotropic characteristics of the most frequently used azo materials.

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Acknowledgements

This work was financial supported by the Bulgarian National Science Fund under project ДH 18/5 “Novel azo materials and application of their photophysical properties as reversible optical optical storage devices”. Research equipment of Distributed Research Infrastructure INFRAMAT, part of Bulgarian National Roadmap for Research Infrastructures, supported by Bulgarian Ministry of Education and Science was used in this investigation.

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  1. Institute of Optical Materials and Technologies, Bulgarian Academy of Science, Acad. G. Bonchev avenue, bldg. 109, Sofia, 1113, Bulgaria

    Blaga Blagoeva, Ani Stoilova, Deyan Dimov, Dimana Nazarova & Anton Georgiev

  2. University of Chemical Technology and Metallurgy, 8 St. Kliment Ohridski Avenue, Sofia, 1756, Bulgaria

    Ani Stoilova & Anton Georgiev

  3. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Science, Acad. G. Bonchev avenue, bldg. 9, Sofia, 1113, Bulgaria

    Dancho Yordanov

  4. Institute of Electronics, Bulgarian Academy of Sciences, 1784, Sofia, Bulgaria

    Liudmil Antonov

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  1. Blaga Blagoeva
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Blagoeva, B., Stoilova, A., Dimov, D. et al. Tautomeric influence on the photoinduced birefringence of 4-substituted phthalimide 2-hydroxy Schiff bases in PMMA matrix. Photochem Photobiol Sci 20, 687–697 (2021). https://doi.org/10.1007/s43630-021-00056-4

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