Synthesis, crystal structure of bis-terpyridinyl-calix[4]arene derivatives and fluorescent sensor for Zn²⁺

Abstract

The calix[4]arene-based podands which incorporates two terpyridinyl functional groups derived from the alkylation reactions of 4-(ω-chloroalkoxyphenyl)-2,2′:6′,2″-terpyridine in 1,3-alternate position at lower rim have been prepared in moderate yields. The structures of four pyridyl compounds were determined by X-ray single crystal diffraction method. The complexing properties of bis-terpyridinyl-calix[4]arenes for transition metal ions were investigated by fluorescence spectra. Bis-terpyridinyl-calix[4]arenes gave a more efficient fluorescent sensing ability to Zn²⁺.

Keywords

Calixarene / Terpyridine / Ionic recognition / Crystal structure

References

[1] Bohmer B. Angew. Chem. Int. Ed. Engl., 1995, 34: 713.

[2] Leininger S, Olenyuk B, Stang P J. Chem. Rev., 2000, 100: 853.

[3] Biros S M, Rebek J Jr. Chem. Soc. Rev., 2007, 36: 93.

[4] Pluth M D, Raymond K N. Chem. Soc. Rev., 2007, 36: 161.

[5] Wieser C, Dielman C, Matt D. Coord. Chem. Rev., 1997, 165: 93.

[6] Harvey P D. Coord. Chem. Rev., 2002, 233/234: 289.

[7] Atwood J L, Barbour L J, Hardie M J, Raston C L. Coord. Chem. Rev., 2001, 222: 3.

[8] Redshaw C. Coord. Chem. Rev., 2003, 244: 45.

[9] Creaven B S, Donlon D F, McGinley J. Coord. Chem. Rev., 2009, 253: 893.

[10] Mokhtari B, Pourabdollah K J. Coord. Chem., 2011, 64: 4079.

[11] Li L, Gu W W, Yan C G. Chem. Res. Chinese Universities, 2010, 26(1): 38.

[12] Sun J, Liu D M, Wang J X, Yan C G. Chem. Res. Chinese Universities, 2010, 26(4): 572.

[13] Sauvage J P, Collin J P, Chambron J C, Guillerez S, Coudret C, Balzani V, Barigelleti L, De Cola L, Flamigni L. Chem. Rev., 1994, 94: 993.

[14] Cargill Thompson A M W. Coord. Chem. Rev., 1997, 160: 1.

[15] Kaes C, Katz A, Hosseini M W. Chem. Rev., 2000, 100: 3553.

[16] Bazzicalupi C, Bencini A, Bianchi A, Danesi A, Faggi E, Giorgi C, Santarelli S, Valtancoli B. Coord. Chem. Rev., 2008, 252: 1052.

[17] Cummings S D. Coord. Chem. Rev., 2009, 253: 1495.

[18] Song P, Sun S G, Zhou P W, Liu J Y, Xu Y Q, Peng X J. Chem. Res. Chinese Universities, 2011, 27(1): 127.

[19] Molard Y, Parrot-Lopez H. Tetrahedron Lett., 2002, 43: 6355.

[20] Pan D, Wu L Z, Tong Z H, Zhang L P. Acta Chim. Sinica, 2006, 64: 1479.

[21] Schröder T, Brodbeck R, Letzel M C, Mix A, Schnatwinkel B, Tonogold M, Volkmer D, Mattay J. Tetrahedron Lett., 2008, 49: 5938.

[22] Liu J M, Tonigold M, Bredenköter B, Schröder T, Mattay J, Volkmer D. Tetrahedron Lett., 2009, 50: 1303.

[23] Lo H S, Yip S K, Wong K M C, Zhu N Y, Yam V W W. Organometallics, 2006, 25: 3537.

[24] Lo H S, Yip S K, Zhu N Y, Yam V W W. Dalton Trans., 2007, 4386.

[25] Zheng G L, Fan W Q, Song S Y, Guo H D, Zhang H J. J. Solid State Chem., 2010, 183: 1457.

[26] Sun J, Xia E Y, Yan C G. J. Coord. Chem., 2012, 6(5): 3086.

[27] Han J, Cai Y H, Liu L, Yan C G, Li Q. Tetrahedron, 2007, 63: 2275.

[28] Sun J, Liu D M, Wang J X, Yan C G. J. Incl. Phenom Macrocycl. Chem., 2009, 64: 317.

[29] Yan C G, Li L, Liu W L. J. Coord. Chem., 2009, 62: 2118.

[30] Sun J, Liu D M, Yan C G. J. Coord. Chem., 2009, 62: 2337.

[31] Gutsche C D, Dhawan B, Leonis M, Stewart H. Org. Synth., 1990, 68: 238.

[32] Winter A, van den Berg A, Hoogenboom R, Kickelbick G, Schubert U. Synthesis, 2006, 2873.