Synthesis and characterization of novel Schiff base macrocyclic compounds containing thiophene

Abstract

Several novel Schiff base macrocyclic compounds containing thiophene were synthesized from diethyl 3,4-dialkoxythiophene-2,5-dicarboxylate, cyanuric chloride, diethylamine and p-nitrophenol by reduction, oxidation, substitution and cyclization, and their structures were characterized by IR, NMR and electrospray ionization-mass spectrometer(ESI-MS). The studies on their UV-Vis absorption spectra show that Schiff base macrocycles 6–10 have selective recognition for Fe³⁺.

Keywords

Ion recognition / Macrocyclic compound / Schiff base / Thiophene

References

[1] Du D M, Hua W T. Chem. J. Chinese Universities, 2003, 24(3): 442.

[2] Yang F, Zhang X J, Chen Q. Chem. J. Chinese Universities, 2011, 32(9): 2010.

[3] Sun Y L, Yang Y W, Wu W. Chem. J. Chinese Universities, 2012, 33(8): 1635.

[4] Stefano P, Carla B, Andrea B. J. Phys. Chem., 2013, 117: 3798.

[5] Daniel G R, Ludger A W. J. Am. Chem. Soc., 2009, 131(10): 3721.

[6] Terence K M L, Zhu N Y, Vivian W W Y. J. Am. Chem. Soc., 2010, 132: 17646.

[7] Lee E, Lee S. Inorg. Chem., 2011, 50: 5803.

[8] Chen L, Zhang H Y, Liu Y. Chem. J. Chinese Universities, 2011, 32(9): 2087.

[9] Yang Y A, Feng W, Yuan L H. Chem. J. Chinese Universities, 2011, 32(9): 1950.

[10] Pilkington N H, Robson R. Aust. J. Chem., 1970, 23: 2225.

[11] Ma C T L, MacLachlan M J. Angew. Chem. Int. Ed., 2005, 44: 4178.

[12] Fenton D F. Chem. Soc. Rev., 1999, 28: 159.

[13] Zheng X L, Jones C W, Weck M. J. Am. Chem. Soc., 2007, 129: 1105.

[14] He Y, Cai C. Catal. Commun., 2011, 12: 678.

[15] Li X A, Hua C W, Gou X F, Zhao J L, Chen B. Chin. J. Org. Chem., 2012, 32: 939.

[16] Song Y M, Zhang Y M, Ma X X, Zhu Z L, Xu J P, Liu J W. Acta Chim. Sinica., 2011, 69: 1347.

[17] Leung D H, Bergman R G, Raymond K N. J. Am. Chem. Soc., 2007, 129: 2746.

[18] Shomura R, Sugiyasu K, Yasuda T, Sato A, Takeuchi M. Macromolecules, 2012, 45: 3759.

[19] Jeong D C, Lee H, Yang K S. Macromolecules, 2012, 45: 9571.

[20] Berlicka A, Lechoslaw L G. Inorg. Chem., 2009, 48: 7922.

[21] Marsella M J, Reid R J, Estassi S, Wang L S. J. Am. Chem. Soc., 2002, 124: 12507.

[22] Trita A S, Roisnel T, Mongin F, Chevallier F. Org. Lett., 2013, 15(14): 3798.

[23] Ngo T H, Berndt H, Lentz D, Reissig H U. J. Org. Chem., 2012, 77: 9676.

[24] Sessler J L, Roznyatovskiy V, Pantos G D, Borisova N E, Reshetova M D, Lynch V M, Khrustalev V N, Ustynyuk Y A. Org. Lett., 2005, 7(23): 5227.

[25] Won D H, Lee C H. Tetrahedron Lett., 2001, 42(10): 1969.

[26] Coffey M, Mckellar B R, Reinhardt B A, Nijakowski T, Feld W A. Synthetic Commun., 1996, 26: 2205.

[27] Liu Y F, Hua C W, Gou X F, Zhao J L. Chin. J. Org. Chem., 2009, 29: 1419.

[28] Sadegh S, Mehdi B. Comput. Theor. Chem., 2011, 971: 30.

[29] Raj K, Iffat M, Nighat F. Spectrochim. Acta. A, 2013, 101: 100.

[30] Saeed M A, Amir A. Chin. Chem. Lett., 2011, 22: 439.

[31] Tanaka K, Shimoura R, Caira R M. Tetrahedron Lett., 2010, 51: 449.