Solid-State Synthesis and Thermochromism of Salicylidene Dinitrophenylhydrazine Derivatives

Jiayi Wang; Yuying Zhou; Biyu Yang; Wanqian Wu; Liyuan Luo; Yongjun Lv

doi:10.14233/ajchem.2016.19521

Issue

Vol. 28 No. 4 (2016): Vol 28 Issue 4

Issue Published : December 30, 2015

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

Solid-State Synthesis and Thermochromism of Salicylidene Dinitrophenylhydrazine Derivatives

https://doi.org/10.14233/ajchem.2016.19521

Jiayi Wang

College of Material and Chemical Engineering, Sichuan University of Science and Engineering, Zigong 643000, Sichuan Province, P.R. China

Yuying Zhou

College of Material and Chemical Engineering, Sichuan University of Science and Engineering, Zigong 643000, Sichuan Province, P.R. China

Biyu Yang

College of Material and Chemical Engineering, Sichuan University of Science and Engineering, Zigong 643000, Sichuan Province, P.R. China

Wanqian Wu

College of Material and Chemical Engineering, Sichuan University of Science and Engineering, Zigong 643000, Sichuan Province, P.R. China

Liyuan Luo

College of Material and Chemical Engineering, Sichuan University of Science and Engineering, Zigong 643000, Sichuan Province, P.R. China

Yongjun Lv

College of Material and Chemical Engineering, Sichuan University of Science and Engineering, Zigong 643000, Sichuan Province, P.R. China

Corresponding Author(s) : Yongjun Lv

yongjunlv@qq.com; lg@licp.cas.cn

Asian Journal of Chemistry, Vol. 28 No. 4 (2016): Vol 28 Issue 4
Article Published : December 30, 2015

Abstract

Two salicylidene dinitrophenylhydrazine compounds (1 and 2) were synthesized by solid-state reaction of (2,4-dinitrophenyl)hydrazine with 2-hydroxybenzaldehyde and 2-hydroxy-1-naphthaldehyde at room temperature, respectively. Their structures were characterized by elemental analysis, ESI-MS and IR and thermochromism properties were investigated by differential scanning calorimetry spectra. The results exhibited that both 1 and 2 displayed significant colour changes relying on temperature, which can be ascribed to the structural transformation between enol and keto forms in the solid state. This transformation may benefit from the intramolecular hydrogen bond and proton H-transfer.

Keywords

Solid-state reaction Thermochromism Schiff base Intramolecular hydrogen bond

Wang, J., Zhou, Y., Yang, B., Wu, W., Luo, L., & Lv, Y. (2015). Solid-State Synthesis and Thermochromism of Salicylidene Dinitrophenylhydrazine Derivatives. Asian Journal of Chemistry, 28(4), 935–936. https://doi.org/10.14233/ajchem.2016.19521

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References

M.C. García-López, B.M. Muñoz-Flores, V.M. Jiménez-Pérez, I. Moggio, E. Arias, R. Chan-Navarro and R. Santillan, Dyes Pigments, 106, 188 (2014); doi:10.1016/j.dyepig.2014.02.021.
Y. Sui, X.N. Fang, R.H. Hu, J. Li and D.S. Liu, Inorg. Chim. Acta, 423, 540 (2014); doi:10.1016/j.ica.2014.09.015.
E. Hadjoudis and I.M. Mavridis, Chem. Soc. Rev., 33, 579 (2004); doi:10.1039/B303644H.
E. Hadjoudis, S.D. Chatziefthimiou and I.M. Mavridis, Curr. Org. Chem., 13, 269 (2009); doi:10.2174/138527209787314797.
M. Xiao, D. Liang, H. Shen, J.Y. Liu and H.Y. Li, IEEE ICICTA, 7, 591 (2014).
S. Hara, H. Houjou, I. Yoshikawa, H. Sato, A. Yamano, Y. Namatame, T. Mutai and K. Araki, J. Phys. Chem. A, 118, 6979 (2014); doi:10.1021/jp5063034.
Z. Yuan, C. Lee and S. Lee, Angew. Chem., 116, 4293 (2004); doi:10.1002/ange.200453995.
S. Anguille, P. Brun and R. Guglielmetti, Appl. Organomet. Chem., 18, 68 (2004); doi:10.1002/aoc.570.
D.A. Safin and Y. Garcia, RSC Adv., 3, 6466 (2013); doi:10.1039/c3ra40705e.
F. Robert, A.D. Naik, B. Tinant, R. Robiette and Y. Garcia, Chem. Eur. J., 15, 4327 (2009); doi:10.1002/chem.200801932.
D.A. Safin, M. Bolte and Y. Garcia, CrystEngComm, 16, 8786 (2014); doi:10.1039/C4CE01325E.
P.U. Biedermann, J.J. Stezowski and I. Agranat, Chem. Eur. J., 12, 3345 (2006); doi:10.1002/chem.200501118.
S. Benard and P. Yu, Chem. Commun., 1, 65 (2000); doi:10.1039/a907675a.
P. Pan, W. Kai, B. Zhu, T. Dong and Y. Inoue, Macromolecules, 40, 6898 (2007); doi:10.1021/ma071258d.
J. Zhang, Y. Duan, H. Sato, H. Tsuji, I. Noda, S. Yan and Y. Ozaki, Macromolecules, 38, 8012 (2005); doi:10.1021/ma051232r.

References

M.C. García-López, B.M. Muñoz-Flores, V.M. Jiménez-Pérez, I. Moggio, E. Arias, R. Chan-Navarro and R. Santillan, Dyes Pigments, 106, 188 (2014); doi:10.1016/j.dyepig.2014.02.021.

Y. Sui, X.N. Fang, R.H. Hu, J. Li and D.S. Liu, Inorg. Chim. Acta, 423, 540 (2014); doi:10.1016/j.ica.2014.09.015.

E. Hadjoudis and I.M. Mavridis, Chem. Soc. Rev., 33, 579 (2004); doi:10.1039/B303644H.

E. Hadjoudis, S.D. Chatziefthimiou and I.M. Mavridis, Curr. Org. Chem., 13, 269 (2009); doi:10.2174/138527209787314797.

M. Xiao, D. Liang, H. Shen, J.Y. Liu and H.Y. Li, IEEE ICICTA, 7, 591 (2014).

S. Hara, H. Houjou, I. Yoshikawa, H. Sato, A. Yamano, Y. Namatame, T. Mutai and K. Araki, J. Phys. Chem. A, 118, 6979 (2014); doi:10.1021/jp5063034.

Z. Yuan, C. Lee and S. Lee, Angew. Chem., 116, 4293 (2004); doi:10.1002/ange.200453995.

S. Anguille, P. Brun and R. Guglielmetti, Appl. Organomet. Chem., 18, 68 (2004); doi:10.1002/aoc.570.

D.A. Safin and Y. Garcia, RSC Adv., 3, 6466 (2013); doi:10.1039/c3ra40705e.

F. Robert, A.D. Naik, B. Tinant, R. Robiette and Y. Garcia, Chem. Eur. J., 15, 4327 (2009); doi:10.1002/chem.200801932.

D.A. Safin, M. Bolte and Y. Garcia, CrystEngComm, 16, 8786 (2014); doi:10.1039/C4CE01325E.

P.U. Biedermann, J.J. Stezowski and I. Agranat, Chem. Eur. J., 12, 3345 (2006); doi:10.1002/chem.200501118.

S. Benard and P. Yu, Chem. Commun., 1, 65 (2000); doi:10.1039/a907675a.

P. Pan, W. Kai, B. Zhu, T. Dong and Y. Inoue, Macromolecules, 40, 6898 (2007); doi:10.1021/ma071258d.

J. Zhang, Y. Duan, H. Sato, H. Tsuji, I. Noda, S. Yan and Y. Ozaki, Macromolecules, 38, 8012 (2005); doi:10.1021/ma051232r.

Issue

Vol. 28 No. 4 (2016): Vol 28 Issue 4

Solid-State Synthesis and Thermochromism of Salicylidene Dinitrophenylhydrazine Derivatives

Corresponding Author(s) : Yongjun Lv

Abstract

Keywords

Full Article

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