Copyright (c) 2024 Ruhul Amin Bepari
This work is licensed under a Creative Commons Attribution 4.0 International License.
Theoretical Validation of Reversible Acidochromism of a Cinnamaldehyde based Scaffold with Experimental Investigations
Corresponding Author(s) : Ruhul Amin Bepari
Asian Journal of Chemistry,
Vol. 36 No. 4 (2024): Vol 36 Issue 4, 2024
Abstract
Present study explores the reversible acidochromism displayed by cinnamaldehyde derivative-based scaffold (P1), which is highly sensitive to variations in acidity and basicity. Upon exposing to an acidic environment, the solution containing P1 undergoes a vivid colour shift from yellow to a vibrant pink-fuchsia colour due to the conversion of imine within P1 into its quinonoid form. The color change can be completely reversed by adding a basic material, demonstrating the reversible acidochromic behavior of the P1 system. Moreover, the practical application of this acidochromic property is demonstrated through the development of a test kit utilizing paper strips. This kit effectively harnesses the acidochromic nature of P1 to detect even minute quantities of acidic or basic substances in solutions. The underlying mechanisms of the acid-base detection and corresponding colorimetric shifts in response to the acid-base interactions have meticulously been explored using density functional theoretical investigations.
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References
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S. Liu, Z. Zhang, Q. Liu, H. Luo and W. Zheng, J. Pharm. Biomed. Anal., 30, 685 (2002); https://doi.org/10.1016/S0731-7085(02)00356-4
K.-H. Kim, W.-C. Shin, Y.-S. Park and S.-S. Yoon, Food Sci. Biotechnol., 16, 99 (2007).
M.J. Kim, S.W. Jung, H.R. Park and S.J. Lee, J. Food Eng., 113, 471 (2012); https://doi.org/10.1016/j.jfoodeng.2012.06.018
A. Brandenburg, R. Edelhauser, T. Werner, H. He and O.S. Wolfbeis, Mikrochim. Acta, 121, 95 (1995); https://doi.org/10.1007/BF01248244
A. Markovics, G. Nagy and B. Kovacs, Sens. Actuators B Chem., 139, 252 (2009); https://doi.org/10.1016/j.snb.2009.02.075
P.T. Snee, R.C. Somers, G. Nair, J.P. Zimmer, M.G. Bawendi and D.G. Nocera, J. Am. Chem. Soc., 128, 13320 (2006); https://doi.org/10.1021/ja0618999
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K. Abe, K. Suzuki and D. Citterio, Anal. Chem., 80, 6928 (2008); https://doi.org/10.1021/ac800604v
S.T. Lee, J. Gin, V.P.N. Nampoori, C.P.G. Vallabhan, N.V. Unnikrishnan and P. Radhakrishnan, J. Opt. A, Pure Appl. Opt., 3, 355 (2001); https://doi.org/10.1088/1464-4258/3/5/307
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S. Jurmanovic, S. Kordic, M.D. Steinberg and I.M. Steinberg, Thin Solid Films, 518, 2234 (2010); https://doi.org/10.1016/j.tsf.2009.07.158
R. Makote and M.M. Collinson, Anal. Chim. Acta, 394, 195 (1999); https://doi.org/10.1016/S0003-2670(99)00305-0
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Y. Hiruta, N. Yoshizawa, D. Citterio and K. Suzuki, Anal. Chem., 84, 10650 (2012); https://doi.org/10.1021/ac302178z
O.S. Wolfbeis, Anal. Chem., 78, 3859 (2006); https://doi.org/10.1021/ac060490z
M.I.J. Stich, L.H. Fischer and O.S. Wolfbeis, Chem. Soc. Rev., 39, 3102 (2010); https://doi.org/10.1039/b909635n
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H.-S. Kim, T.D. Chung and H. Kim, J. Electroanal. Chem., 498, 209 (2001); https://doi.org/10.1016/S0022-0728(00)00413-7
W.C. Barrette, H.W. Johnson and D.T. Sawyer, Anal. Chem., 56, 1890 (1984); https://doi.org/10.1021/ac00275a030
C. Reichardt, Chem. Rev., 94, 2319 (1994); https://doi.org/10.1021/cr00032a005
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I.M. Kolthoff, M.K. Chantooni and S. Bhowmik, Anal. Chem., 39, 315 (1967); https://doi.org/10.1021/ac60247a047
S. Wakabayashi, Y. Kato, K. Mochizuki, R. Suzuki, M. Matsumoto, Y. Sugihara and M. Shimizu, J. Org. Chem., 72, 744 (2007); https://doi.org/10.1021/jo061684h
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S. Grimme, A. Hansen, J.G. Brandenburg and C. Bannwarth, Chem. Rev., 116, 5105 (2016); https://doi.org/10.1021/acs.chemrev.5b00533
B. Saha and P.K. Bhattacharyya, New J. Chem., 47, 12790 (2023); https://doi.org/10.1039/D3NJ01797D
J. Tomasi, B. Mennucci and R. Cammi, Chem. Rev., 105, 2999 (2005); https://doi.org/10.1021/cr9904009
T. Helgaker, S. Coriani, P. Jorgensen, K. Kristensen, J. Olsen and K. Ruud, Chem. Rev., 112, 543 (2012); https://doi.org/10.1021/cr2002239
A.E. Reed, L.A. Curtiss and F. Weinhold, Chem. Rev., 88, 899 (1988); https://doi.org/10.1021/cr00088a005