Synthesis and properties of functionalized Schiff bases of 5α,10α-di(4-hydroxylphenyl)calix[4]pyrrole and 5α,15β-di(4-hydroxylphenyl)calix[4]pyrrole

Abstract

A series of calix[4]pyrrole meso-substituted Schiff bases was synthesized with 5α,10α-di(4-hydroxylphenyl)calix[4]pyrrole or 5α,15β-di(4-hydroxylphenyl)calix[4]pyrrole as starting material. The synthetic routes included alkylation with methyl α-chlroroaceate, ammonolysis with alkylene diamine, and condensation with salicylladehyde or 2-hydroxynaphthaldehyde. The crystal structures of the new calix[4]pyrroles and their Schiff bases were determined by X-ray diffraction. The coordination properties of the representative calix[4]pyrrole Schiff bases to transition metal ions were also investigated by UV-Vis spectra.

Keywords

Calix[4]pyrrole / Schiff base / Macrocycle / Crystal structure / UV-Vis spectroscopy

References

[1] Allen W E, Gale P A, Brown C T, Lynch V M, Sessler J L. J. Am. Chem. Soc., 1996, 118(49): 12471.

[2] Gale P A, Anzenbacher P, Sessler J L. Coord. Chem. Rev., 2001, 222(1): 57.

[3] Gale P A. Coord. Chem. Rev., 2003, 240(1/2): 191.

[4] Gale P A, Quesada R. Coord. Chem. Rev., 2006, 250(23/24): 3219.

[5] Gale P A, García-Garrido S E, Garric J. Chem. Soc. Rev., 2008, 37(1): 151.

[6] Matano Y, Imahori H. Acc. Chem. Res., 2009, 42(8): 1193.

[7] Gale P A. Acc. Chem. Res., 2011, 44(3): 216.

[8] Levitskaia T G, Marquez M, Sessler J L, Shriver J A, Vercouter T, Moyer B A. Chem. Commun., 2003, 2248.

[9] Ji X K, Black D St C, Colbran S B, Craig D C, Edbey K M, Harper J B, Willett G D. Tetrahedron, 2005, 61(45): 10705.

[10] Garg B, Bisht T, Chauhan S M S. J. Incl. Phenom. Macrocycl. Chem., 2011, 70(1/2): 249.

[11] Garg B, Ling Y C. Tetrahedron Lett., 2012, 53(42): 5674.

[12] Taner B. J. Incl. Phenom. Macrocycl. Chem., 2014, 79(1/2): 75.

[13] Miyaji H, Kim H K, Sim E K, Lee C K, Cho W S, Sessler J L, Lee C H. J. Am. Chem. Soc., 2005, 127(36): 12510.

[14] Taner B, Deveci P, Bereket S, Solak A S, Oecan E. Inorg. Chim. Acta, 2010, 363(14): 4017.

[15] Kim K J, Gross D E, Cho D G, Lynch V M, Sessler J L. J. Org. Chem., 2011, 76(4): 1005.

[16] Cafeo G, Kohnke F H, Parisi M F, Nascone R P, La Torre G L, Williams D J. Org. Lett., 2002, 4(16): 2695.

[17] Cafeo G, Kohnke F H, La Torre G L, Parisi M F, Nascone R P, White A J P, Williams D J. Chem. Eur. J., 2002, 8(14): 3148.

[18] Song M Y, Na H K, Kim E Y, Lee S J, Kim K I, Baek E M, Kim H S, An D K, Lee C H. Tetrahedron Lett., 2004, 45(2): 299.

[19] Sessler J L, An D, Cho W S, Lynch V, Yoon D W, Hong S J, Lee C H. J. Org. Chem., 2005, 70(5): 1511.

[20] Mokhtari B, Pourabdollah K. J. Incl. Phenom. Macrocycl. Chem., 2013, 77(1/4): 23.

[21] Taner B, Kursunlu A N, Güler E. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 11(824): 903.

[22] Bhatt K D, Vyas D J, Makwana B A, Darjee S M, Jain V K. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 121(5): 94.

[23] Lee C H, Lee J S, Na H K, Yoon D Y, Miyaji H, Cho W S, Sessler J L. J. Org. Chem., 2005, 70(6): 2067.

[24] Cafeo G, Colquhoun H M, Cuzzola A, Gattuso M, Kohnke F H, Valenti L, White A J P. J. Org. Chem., 2010, 75(18): 6263.

[25] Guchhait T, Mani G. J. Org. Chem., 2011, 76(24): 10114.

[26] Aydogan A, Akar A. Chem. A. Eurp. J., 2012, 18(7): 1999.

[27] Han Y, Wang G L, Sun J J, Sun J, Yan C G. Tetrahedron, 2013, 69(49): 10604.

[28] Farinha A S F, Fernandes M R C, Tomé A C. Sensors and Actuators B: Chemical, 2014, 200: 332.

[29] Yan C G, Chen W F, Chen J, Jiang T T, Yao Y. Tetrahedron, 2007, 63(39): 9614.

[30] Yan C G, Li L, Liu W L. J. Coord. Chem., 2009, 6213: 2118.

[31] Sun J, Liu D M, Wang J X, Yan C G. J. Coord. Chem., 2009, 62(14): 2337.

[32] Liu L, Huang K, Yan C G. J. Incl. Phenom Macrocycl. Chem., 2010, 66(3/4): 349.

[33] Huang K, Liu K, Yan C G. Chem. Res. Chinese Universities, 2014, 30(2): 245.

[34] Sun J, Zhang L L, Yao Y, Yan C G. J. Incl. Phenom. Macrocyclic. Chem., 2014, 79(3/4): 485.