Copyright (c) 2024 Kilaru Padma Suhasini, Jayanthi Suresh Kumar, Voosala Christopher, Challa Gangu Naidu
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization of New Benzopyran Pyrimidines and Study of their Solvatochromic Behaviour
Corresponding Author(s) : Kilaru Padma Suhasini
Asian Journal of Chemistry,
Vol. 36 No. 4 (2024): Vol 36 Issue 4, 2024
Abstract
Five new benzopyran pyrimidines (5a-e) were synthesized in three steps by using silica-sulphuric acid as catalyst. All the synthesized benzopyran pyrimidines with various substituents were characterized by spectroscopic techniques such as 1H NMR, 13C NMR, IR and mass spectroscopy. The structural features of these molecules containing pyrimidine ring with π-conjugated systems and various functional groups on the aromatic rings greatly influence their photophysical properties. Thus, they behave as better candidates for developing the photoelectric materials. Thus, it is proposed to synthesize, characterize and study their solvatochromic behaviour in various polar and non-polar organic solvents viz. dichloromethane, tetrahydrofuran, ethyl acetate, acetonitile and ethanol. Interestingly, all the target molecules exhibited greater Stoke’s shift (λf-λa) in dichloromethane except for compound 5e, which exhibited greater value in tetrahydrofuran, possibly due to the moderately polar nature of the solvent. The synthesized benzopyran pyrimidines displayed solvatochromic characteristics due to the presence of multiple substituted functional groups on the rings in different organic solvents. Due to their remarkable properties, they could serve as potential candidate molecules for future investigations into photoelectric materials.
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References
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S. Achelle, Y. Ramondenc, G. Dupas and N. Plé, Tetrahedron, 64, 2783 (2008); https://doi.org/10.1016/j.tet.2008.01.037
G. Schull, L. Douillard, C. Fiorini-Debuisschert, F. Charra, F. Mathevet, D. Kreher and A.-J. Attias, Adv. Mater., 18, 2954 (2006); https://doi.org/10.1002/adma.200600683
S. Diring, P. Retailleau and R. Ziessel, Tetrahedron Lett., 48, 8069 (2007); https://doi.org/10.1016/j.tetlet.2007.09.011
J.-C.G. Bunzli and C. Piguet, Chem. Soc. Rev., 34, 1048 (2005); https://doi.org/10.1039/b406082m
H. Meier, E. Karpuk and H. Christof Holst, Eur. J. Org. Chem., 22, 2609 (2006); https://doi.org/10.1002/ejoc.200600066
Y. Yamaguchi, S. Kobayashi, T. Wakamiya, Y. Matsubara and Z. Yoshida, Angew. Chem. Int. Ed., 44, 7040 (2005); https://doi.org/10.1002/anie.200502214
J.Y. Jaung, Dyes Pigments, 71, 245 (2006); https://doi.org/10.1016/j.dyepig.2005.07.008
R. Cristiano, E. Westphal, I.H. Bechtold, A.J. Bortoluzzi and H. Gallardo, Tetrahedron, 63, 2851 (2007); https://doi.org/10.1016/j.tet.2007.01.045
K. Itami, D. Yamazaki and J. Yoshida, J. Am. Chem. Soc., 126, 15396 (2004); https://doi.org/10.1021/ja044923w
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E.V. Verbitskiy, A.A. Baranova, K.I. Lugovik, K.O. Khokhlov, E.M. Cheprakova, G.L. Rusinov, O.N. Chupakhin and V.N. Charushin, ARKIVOC, 360 (2016); https://doi.org/10.3998/ark.5550190.p009.470
M. Fecková, P. le Poul, F. Bureš, F. Robin-le Guen and S. Achelle, Dyes Pigments, 182, 108659 (2020); https://doi.org/10.1016/j.dyepig.2020.108659
D. Habibi, H. Nabavi and M. Nasrollahzadeh, J. Chem., 2013, 645313 (2013); https://doi.org/10.1155/2013/645313
M. Mamouei, K. Budidha, N. Baishya, M. Qassem and P.A. Kyriacou, Sci. Rep., 11, 13734 (2021); https://doi.org/10.1038/s41598-021-92850-4
A. Pathak and M. Kumar, The Scientific Temper, 13, 208 (2022).
J. Jana, T. Aditya, Y. Negishi and T. Pal, ACS Omega, 2, 8086 (2017); https://doi.org/10.1021/acsomega.7b01560
H. Detert, M. Lehmann and H. Meier, Materials, 3, 3218 (2010); https://doi.org/10.3390/ma3053218
M. Rajeshirke, M. Kadam and N. Sekar, Fibers Polym., 20, 320 (2019); https://doi.org/10.1007/s12221-019-8317-1
S.A. Sharber, R.N. Baral, F. Frausto, T.E. Haas, P. Muller and S.W. Thomas III, J. Am. Chem. Soc., 139, 5164 (2017); https://doi.org/10.1021/jacs.7b00878
C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim (1988).