European Journal of Chemistry

Synthesis, photochromic, and electrochromic properties of a Schiff-base pyrazolone: An experimental and theoretical study

Crossmark


Main Article Content

Pratima Surati

Abstract

Schiff-base pyrazolone derivatives have garnered significant attention due to their intriguing photochromic and electrochromic properties, which hold promise for applications in molecular switches, sensors, and advanced optical materials. Schiff base, 5-methyl-2-phenyl-4-(phenyl-o-tolylamino-methylene)-2,4-dihydropyrazol-3-one (PMBP-2A1MB), was synthesized and characterized by means of NMR, IR, LC-MS, and UV-Vis absorption spectra. This research paper aims to dive into the synthesis and photochromic and electrochromic properties of Schiff base pyrazolone derivative. The photochromic study was investigated using 365 and 430 nm light and shows good results. The electrochromic study was conducted using a cyclic voltammetry study, which demonstrates quasi-reversibility in nature. Theoretical calculations were performed using geometries optimized at the B3LYP/6-31G(d,p) level of theory. By integrating these aspects, we seek to enhance the understanding of photoisomerization and structure-property relationships.


icon graph This Abstract was viewed 5 times | icon graph Article PDF downloaded 1 times

How to Cite
(1)
Surati, P. Synthesis, Photochromic, and Electrochromic Properties of a Schiff-Base Pyrazolone: An Experimental and Theoretical Study. Eur. J. Chem. 2026, 17, 138-145.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Irie, M. Diarylethenes for Memories and Switches. Chem. Rev. 2000, 100 (5), 1685-1716.
https://doi.org/10.1021/cr980069d

[2]. Nitschke, P.; Jarząbek, B.; Damaceanu, M.; Bejan, A.; Chaber, P. Spectroscopic and electrochemical properties of thiophene-phenylene based Shiff-bases with alkoxy side groups, towards photovoltaic applications. Spectrochim. Acta A: Mol. Biomol. Spec. 2021, 248, 119242.
https://doi.org/10.1016/j.saa.2020.119242

[3]. Cozzi, P. G. Metal-Salen Schiff base complexes in catalysis: practical aspects. Chem. Soc. Rev. 2004, 33 (7), 410-421.
https://doi.org/10.1039/B307853C

[4]. Ko, C.; Yam, V. W. Coordination Compounds with Photochromic Ligands: Ready Tunability and Visible Light-Sensitized Photochromism Acc. Chem. Res. 2017, 51 (1), 149-159.
https://doi.org/10.1021/acs.accounts.7b00426

[5]. Chemes, D. M.; Alonso de Armiño, D. J.; Cutin, E. H.; Oberhammer, H.; Robles, N. L. Synthesis, characterization and vibrational studies of p-chlorosulfinylaniline. J. Mol. Struct. 2017, 1127, 191-198.
https://doi.org/10.1016/j.molstruc.2016.06.067

[6]. Ru, Y.; Shi, Z.; Zhang, J.; Wang, J.; Chen, B.; Huang, R.; Liu, G.; Yu, T. Recent progress of photochromic materials towards photocontrollable devices. Mater. Chem. Front. 2021, 5 (21), 7737-7758.
https://doi.org/10.1039/D1QM00790D

[7]. Gentili, P. L. Chemical AI in the Limelight: The Contribution of Photochromic Materials and Oscillatory Chemical Reactions. Advanced Optical Materials 2025, 13 (15), https://doi.org/10.1002/adom.202500016.
https://doi.org/10.1002/adom.202500016

[8]. Gu, C.; Jia, A.; Zhang, Y.; Zhang, S. X. Emerging Electrochromic Materials and Devices for Future Displays. Chem. Rev. 2022, 122 (18), 14679-14721.
https://doi.org/10.1021/acs.chemrev.1c01055

[9]. Monk, P.; Mortimer, R.; Rosseinsky, D. Electrochromism and Electrochromic Devices. Cambridge University Press, 2007.
https://doi.org/10.1017/CBO9780511550959

[10]. Singh, R. K.; Singh, A. K. Synthesis, molecular structure, spectral analysis, natural bond order and intramolecular interactions of 2-acetylpyridine thiosemicarbazone: A combined DFT and AIM approach. J. Mol. Struct. 2015, 1094, 61-72.
https://doi.org/10.1016/j.molstruc.2015.03.064

[11]. Hariharan, P. C.; Pople, J. A. The influence of polarization functions on molecular orbital hydrogenation energies. Theoret. Chim. Acta 1973, 28 (3), 213-222.
https://doi.org/10.1007/BF00533485

[12]. Liu, G.; Liu, L.; Jia, D.; Yu, K. Synthesis, Structure and Photochromic Properties of 1-Phenyl-3-Methyl-4-(4-Bromobenzal)-Pyrazolone-5 Thiosemicarbazone. Struct. Chem. 2005, 16 (2), 135-140.
https://doi.org/10.1007/s11224-005-2837-6

[13]. Wang, J.; Liu, L.; Liu, G.; Guo, J.; Jia, D. Three novel photoisomeric compounds of the 4-acyl pyrazolone derivants: Crystal structures and substituent effects on photo-isomerism in solid state. Sci. China. Ser. B-Chem. 2008, 51 (7), 661-668.
https://doi.org/10.1007/s11426-008-0025-4

[14]. Peng, B.; Liu, G.; Liu, L.; Jia, D.; Yu, K. Crystal structure and spectroscopic study on photochromism of 1-phenyl-3-methyl-4-benzal-5-pyrazolone 4-ethylthiosemicarbazone. J. Mol. Struct. 2004, 692 (1-3), 217-222.
https://doi.org/10.1016/j.molstruc.2004.02.001

[15]. Liu, L.; Jia, D.-Z.; Ji, Y.-L.; Yu, K.-B. Crystal structure and photochromism of 1-phenyl-3-methyl-4-benzyl-5-one-pyrazole S-methyl thiosemicarbazone. J. Mol. Struct. 2003, 655, 221-227.
https://doi.org/10.1016/S0022-2860(03)00251-5

[16]. Saha Halder, S.; Roy, S.; Kumar Mondal, T.; Saha, R.; Sinha, C. 1‐Alkyl‐2‐{(O‐Thioalkyl)Phenylazo}Imidazole Complexes of PbII and Their Photochromic Property. Zeitschrift. Anorg. Allge. Chemie 2013, 639 (10), 1861-1870.
https://doi.org/10.1002/zaac.201300173

[17]. Surati, P. R. Photochromic and Photoswitchable Study of Pyrazolone-Based Compound and Its Ni(II) ion Sensing Ability. J. Anal. Chem. 2022, 77 (8), 1010-1014.
https://doi.org/10.1134/S106193482208010X

[18]. Irie, M.; Fukaminato, T.; Matsuda, K.; Kobatake, S. Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators. Chem. Rev. 2014, 114 (24), 12174-12277.
https://doi.org/10.1021/cr500249p

[19]. Bléger, D.; Hecht, S. Visible‐Light‐Activated Molecular Switches. Angew. Chem. Int. Ed. 2015, 54 (39), 11338-11349.
https://doi.org/10.1002/anie.201500628

[20]. Altun, Y.; Köseoğlu, F. Solute-Solvent Interaction Effects on Protonation Equilibrium of Substituted N-Benzylidene-2-hydroxyanilines in Aqueous Ethanol: The Application of Factor Analysis to Solvatochromic Parameters and Protonation Equilibria. Monatsh. Chem. 2006, 137 (6), 703-716.
https://doi.org/10.1007/s00706-005-0477-6

[21]. Shah, B. A.; Surati, P. R.; Shah, A. V. Chemionics Study of Newly Synthesized Photochromic Schiff Base Compound. Molecular. Crystals. and. Liquid. Crystals. 2013, 575 (1), 115-127.
https://doi.org/10.1080/15421406.2013.766918

[22]. Chong, D. P. Recent Advances in Density Functional Methods. Recent. Advances. in. Computational. Chemistry. 1995, https://doi.org/10.1142/2914.
https://doi.org/10.1142/2914

[23]. Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Principles of molecular photochemistry: An introduction; University Science Books: Sausalito, CA, 2009.

[24]. Mortimer, R. J. Electrochromic materials. Chem. Soc. Rev. 1997, 26 (3), 147-156.
https://doi.org/10.1039/cs9972600147

[25]. Onur, E.; Lee, J.; Aymerich-Armengol, R.; Lim, J.; Dai, Y.; Tüysüz, H.; Scheu, C.; Weidenthaler, C. Exploring the Effects of the Photochromic Response and Crystallization on the Local Structure of Noncrystalline Niobium Oxide. ACS. Appl. Mater. Interfaces. 2024, 16 (19), 25136-25147.
https://doi.org/10.1021/acsami.4c04038

[26]. Algi, M. P.; Cihaner, A.; Algi, F. Design, synthesis, photochromism and electrochemistry of a novel material with pendant photochromic units. Tetrahedron 2014, 70 (34), 5064-5072.
https://doi.org/10.1016/j.tet.2014.06.005

[27]. Zhang, J.; Zou, Q.; Tian, H. Photochromic Materials: More Than Meets The Eye. Advanced Materials 2012, 25 (3), 378-399.
https://doi.org/10.1002/adma.201201521

[28]. Duan, C.; Cai, W.; Huang, F.; Zhang, J.; Wang, M.; Yang, T.; Zhong, C.; Gong, X.; Cao, Y. Novel Silafluorene-Based Conjugated Polymers with Pendant Acceptor Groups for High Performance Solar Cells. Macromolecules 2010, 43 (12), 5262-5268.
https://doi.org/10.1021/ma100616f

[29]. Wu, X.; Wang, W.; Li, B.; Hou, Y.; Niu, H.; Zhang, Y.; Wang, S.; Bai, X. Synthesis and electrochromic, acidochromic properties of Schiff bases containing triphenylamine and thiophene units. Spectrochim Acta A: Mol. Biomol. Spectr. 2015, 140, 398-406.
https://doi.org/10.1016/j.saa.2015.01.007

[30]. Areephong, J.; Browne, W. R.; Katsonis, N.; Feringa, B. L. Photo- and electro-chromism of diarylethene modified ITO electrodes-towards molecular based read-write-erase information storage. Chem. Commun. 2006, 3930-3932.
https://doi.org/10.1039/B608502D

[31]. Castro, M. R.; Schellenberg, P.; Belsley, M.; Fonseca, A. C.; Fernandes, S. S.; Raposo, M. M. Design, synthesis and evaluation of redox, second order nonlinear optical properties and theoretical DFT studies of novel bithiophene azo dyes functionalized with thiadiazole acceptor groups. Dyes Pigments 2012, 95 (2), 392-399.
https://doi.org/10.1016/j.dyepig.2012.05.014

[32]. Guo, J.; Ren, T.; Zhang, J.; Li, G.; Li, W.; Yang, L. Crystal structure characterization as well as theoretical study of spectroscopic properties of novel Schiff bases containing pyrazole group. Spectrochim. Acta A: Mol. Biomol. Spectr. 2012, 95, 135-142.
https://doi.org/10.1016/j.saa.2012.04.065

[33]. Jacquemin, D.; Wathelet, V.; Perpète, E. A.; Adamo, C. Extensive TD-DFT Benchmark: Singlet-Excited States of Organic Molecules. J. Chem. Theory. Comput. 2009, 5 (9), 2420-2435.
https://doi.org/10.1021/ct900298e

[34]. Chai, H.; Liu, G.; Liu, L.; Jia, D. Synthesis and spectroscopic study on photochromism of a new thiosemicarbazone compound containing pyrazolone. Spectrochim. Acta A: Mol. Biomol. Spectr. 2005, 61 (11-12), 2590-2594.
https://doi.org/10.1016/j.saa.2004.09.027

[35]. Liu, H.; Guo, J.; Jia, D.; Guo, M.; Liu, L.; Wu, D. Fluorescence modulation of a pyrazolone dye in the solid state based on energy transfer. New. J. Chem. 2015, 39 (12), 9866-9871.
https://doi.org/10.1039/C5NJ01781E

[36]. Surati, P. R.; Shah, B. A. Photochromic and molecular switching behaviour of Schiff base-containing pyrazolone ring. Chemical Papers 2015, 69 (2), https://doi.org/10.1515/chempap-2015-0021.
https://doi.org/10.1515/chempap-2015-0021

[37]. Guo, Y.; Liu, G.; Liu, L.; Jia, D. A theoretical study of the photochromic mechanism of a novel photochromic compound: 1-phenyl-3-methyl-4-(4-bromobenzal) pyrazolone-5 thiosemicarbazone. J. Mol. Struct: THEOCHEM 2004, 712 (1-3), 223-231.
https://doi.org/10.1016/j.theochem.2004.10.031

[38]. Hadjoudis, E.; Mavridis, I. M. Photochromism and thermochromism of Schiff bases in the solid state: structural aspects. Chem. Soc. Rev. 2004, 33 (9), 579-588.
https://doi.org/10.1039/b303644h

[39]. Amimoto, K.; Kawato, T. Photochromism of organic compounds in the crystal state. J. Photochem. Photobio. C: Photochem. Rev. 2005, 6 (4), 207-226.
https://doi.org/10.1016/j.jphotochemrev.2005.12.002

[40]. Surati, P. R. Photochromic and Electrochromic Study of Schiff Bases Containing Pyrazolone and Anthracene Unit. J. Struct. Chem. 2023, 64 (6), 984-994.
https://doi.org/10.1134/S0022476623060033

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms
Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

License Terms

by-nc

Copyright © 2026 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).