Photochromic and molecular switching behaviour of Schiff base-containing pyrazolone ring
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Abstract
A new Schiff base compound, 4-[[(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylidene] amino]-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one (I ), was synthesised and characterised by elemental analysis and LC-MS, FTIR and 1H NMR spectra. The photochromic property of the synthesised compound investigated under 365 nm UV irradiation can be observed by solid state absorption and fluorescence spectra. The kinetic study showed that the photochromic reaction was of the pseudo-first-order. The photo-isomerisation was due to photo-induced intermolecular hydrogen bonding, which resulted in enol to keto transformation. The molecular switching behaviour was studied in solution with two inputs in three different systems (OH− and Ag+), (OH− and Cd2+) and (OH− and Th4+) based on the UV absorption spectra. It exhibited the logic behaviour of XNOR, AND and NOR for Ag+, Cd2+ and Th4+ in alkaline media, respectively.
References
Ballardini, R., Ceroni, P., Credi, A., Gandolfi, M. T., Maestri, M., Semararo, M., Venturi, M., & Balzani, V. (2007). Molecular photochemionics. Advanced Functional Materials, 17, 740-750. DOI: 10.1002/adfm.200600992.10.1002/adfm.200600992Search in Google Scholar
Budyka, M. F., Potashova, N. I., Gavrishova, T. N., & Lee, V. M. (2008). Molecular logic gates based on 2-tyrylquinoline derivatives. Russian Chemical Bulletin, 57, 2586-2591. DOI: 10.1007/s11172-008-0372-5.10.1007/s11172-008-0372-5Search in Google Scholar
Budyka, M. F. (2010). Molecular photonic logic gates. High Energy Chemistry, 44, 121-126. DOI: 10.1134/s0018143910020 062.Search in Google Scholar
Chai, H., Liu, G., Liu, L., & Jia, D. (2005). Synthesis and spectroscopic study on photochromism of a new thiosemicarbazone compound containing pyrazolone. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 61, 2590-2594. DOI: 10.1016/j.saa.2004.09.027.10.1016/j.saa.2004.09.027Search in Google Scholar
Denisov, G. S., Golubev, N. S., Schreiber, V.M., Shajakhmedov, S. S., & Shurukhina, A. V. (1997). Effect of intermolecular hydrogen bonding and proton transfer on fluorescence of salicylic acid. Journal of Molecular Structure, 436-437, 153-160. DOI: 10.1016/s0022-2860(97)00136-1.10.1016/S0022-2860(97)00136-1Search in Google Scholar
Ding, H., Liu, G., Pu, S., & Zheng, C. (2014). Multi-addressable fluorescent switch based on a photochromic diarylethene with triazole-bridged methylquinoline group. Dyes and Pigments, 103, 82-88. DOI: 10.1016/j.dyepig.2013.11.022.10.1016/j.dyepig.2013.11.022Search in Google Scholar
Guo, X., Zhang, D., & Zhu, D. (2004). Logic control of the fluorescence of a new dyad, spiropyran-perylene diimidespiropyran, with light, ferric ion, and proton: Construction of a new three-input “AND” logic gate. Advanced Materials, 16, 125-130. DOI: 10.1002/adma.200306102.10.1002/adma.200306102Search in Google Scholar
Guo, J., Jia, D., Liu, L., Yuan, H., Guo, M., Wu, D., & Li, F. (2011). Photochromism and mechanism of pyrazolones in crystals: structural variations directly observed by Xray diffraction. Journal of Materials Chemistry, 21, 12202-12205. DOI: 10.1039/c1jm12267c.10.1039/c1jm12267cSearch in Google Scholar
Kawato, T., Koyama, H., Kanatomi, H., & Isshiki, M. (1985). Photoisomerization and thermoisomerization I: Unusual photochromism of N-(3,5-di-tert-butyl-salicylidene) amines. Journal of Photochemistry, 28, 103-110. DOI: 10.1016/0047-2670(85)87020-9.10.1016/0047-2670(85)87020-9Search in Google Scholar
Lee, C. W., Song, Y. H., Lee, Y., Ryu, K. S., & Chi, K. W. (2009). Reversible photochromic switch ensemble and its photoimaging using H+ transfer between spiropyran and fluorescein in a polymer matrix. Chemical Communications, 2009, 6282-6284. DOI: 10.1039/b913096a.10.1039/b913096aSearch in Google Scholar
Liu, L., Jia, D. Z., Ji, Y. L., & Yu, K. B. (2003). Synthesis, structure and photochromic properties of 4-acyl pyrazolone derivants. Journal of Photochemistry and Photobiology A: Chemistry, 154, 117-122. DOI: 10.1016/s1010-6030(02)00321-0.10.1016/S1010-6030(02)00321-0Search in Google Scholar
Natali, M., Soldi, L., & Giordani, S. (2010). A photoswitchable Zn (II) selective spiropyran-based sensor. Tetrahedron, 66, 7612-7617. DOI: 10.1016/j.tet.2010.07.035.10.1016/j.tet.2010.07.035Search in Google Scholar
Park, I. S., Heo, E., Nam, Y. S., Lee, C. W., & Kim, J. M. (2012). Colorimetric detection of aliphatic primary amines and a molecular logic gate based on a photochromic phenoxyquinone derivative. Journal of Photochemistry and Photobiology A: Chemistry, 238, 1-6. DOI: 10.1016/j. jphotochem.2012.04.003.Search in Google Scholar
Peng, B., Liu, G., Liu, L., Jia, D., & Yu, K. (2004). Crystal structure and spectroscopic study on photochromism of 1- phenyl-3-methyl-4-benzal-5-pyrazolone 4-ethylthiosemicarbazone. Journal of Molecular Structure, 692, 217-222. DOI: 10.1016/j.molstruc.2004.02.001.10.1016/j.molstruc.2004.02.001Search in Google Scholar
Peng, B., Liu, G., Liu, L., & Jia, D. (2005). Studies on solidstate proton transfer along hydrogen bond of pyrazolone-ring. Tetrahedron, 61, 5926-5932. DOI: 10.1016/j.tet.2005.03.096.10.1016/j.tet.2005.03.096Search in Google Scholar
Piao, X., Zou, Y., Wu, J., Li, C., & Yi, T. (2009). Multiresponsive switchable diarylethene and its application in bioimaging. Organic Letters, 11, 3818-3821. DOI: 10.1021/ol9014267.10.1021/ol9014267Search in Google Scholar
Pu, S., Jiang, D., Liu, W., Liu, G., & Cui, S. (2012). Multiaddressable molecular switches based on photochromic diarylethenes bearing a rhodamine unit. Journal of Materials Chemistry, 22, 3517-3526. DOI: 10.1039/c2jm15262b.10.1039/c2jm15262bSearch in Google Scholar
Pu, S., Tong, Z., Liu, G., & Wang, R. (2013). Multi-addressable molecular switches based on a new diarylethene salicylal Schiff base derivative. Journal of Materials Chemistry C, 1, 4726-4739. DOI: 10.1039/c3tc30804a.10.1039/c3tc30804aSearch in Google Scholar
Saleh, A. A., Pleune, B., Fettinger, J. C., & Poli, R. (1997). Hydrotris( pyrazolyl)borate molybdenum chemistry: spin triplet 16-electron carbonyl derivatives of molybdenum(II), and the X-ray structure of the Mo(V) oxo compound {HB(3,5- Me2C3N2H)3}MoOI2. Polyhedron, 16, 1391-1397. DOI: 10. 1016/s0277-5387(96)00392-0.10.1016/S0277-5387(96)00392-0Search in Google Scholar
Shah, B. A., Surati, P. R., & Shah, A. V. (2013). Chemionics study of newly synthesized photochromic Schiff base compound. Molecular Crystals and Liquid Crystals, 575, 115-127. DOI: 10.1080/15421406.2013.766918.10.1080/15421406.2013.766918Search in Google Scholar
Singh, P., & Kumar, S. (2006). Photonic logic gates based on metal ion and proton induced multiple outputs in 5-chloro-8-hydroxyquinoline based tetrapod. New Journal of Chemistry, 30, 1553-1556. DOI: 10.1039/b607524j.10.1039/b607524jSearch in Google Scholar
Tian, H., & Wang, S. (2007). Photochromic bisthienylethene as multi-function switches. Chemical Communications, 2007, 781-792. DOI: 10.1039/b610004j.10.1039/B610004JSearch in Google Scholar PubMed
Xie, X., Liu, L., Jia, D., Guo, J., Wu, D., & Xie, X. (2009). Photo-switch and INHIBIT logic gate based on two pyrazolone thiosemicarbazone derivatives. New Journal of Chemistry, 33, 2232-2240. DOI: 10.1039/b908326j.10.1039/b908326jSearch in Google Scholar
Zhang, J. F., Zhou, Y., Yoon, J., & Kim, J. S. (2011). Recent progress in fluorescent and colorimetric chemosensors for detection of precious metal ions (silver, gold and platinum ions). Chemical Society Reviews, 40, 3416-3429. DOI: 10.1039/c1cs15028f. 10.1039/c1cs15028fSearch in Google Scholar PubMed
© 2015 Institute of Chemistry, Slovak Academy of Sciences
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- Self-penetrating and interpenetrating 3D metal–organic frameworks constructed from 4-(4-carboxyphenoxy)-phthalic acid and N-donor auxiliary ligands
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- Promoting effect of group VI metals on Ni/MgO for catalytic growth of carbon nanotubes by ethylene chemical vapour deposition
- Microwave-assisted solvent-free synthesis and luminescence properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles
- Synthesis of potential inhibitors of glycosyltransferases representing UDP-GlcNAc
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