Highly selective fluoride recognition by a simple carbazole-based hydrozone derivative

Abstract

A simple carbazole hydrozone derivative(1) was synthesized and used as an optical probe for fluoride recognition in CH₃CN. Receptor 1 exhibited colorimetric and fluorescent dual-channel response to fluoride anions. Addition of fluoride to a receptor 1 solution in CH3CN induced a distinct color change from yellow to magenta, the solution also displayed significant fluorescence blue shift. Thus receptor 1 exhibited dual-channel responses to fluoride with a high selectivity and sensitivity.

Keywords

Fluoride ion / Carbazole / Colorimetric / Fluorescent

References

[1] Beer P. D., Gale P. A. Angew. Chem. Int. Ed., 2001, 40: 486.

[2] Schmidtchen F. P., Berger M. Chem. Rev., 1997, 97: 1609.

[3] Wenzel M., Hiscock J. R., Gale P. A. Chem. Soc. Rev., 2012, 41: 480.

[4] Moragues M. E., Martínez M. R., Sancenón F. Chem. Soc. Rev., 2011, 40: 2593.

[5] Fu T. M., Wu C. Y., Cheng C. C., Yang C. R., Yen Y. P. Sens. Actuators B, 2010, 146: 171.

[6] Li A. F., Wang J. H., Wang F., Jiang Y. B. Chem. Soc. Rev., 2010, 39: 3729.

[7] Caltagirone C., Hiscock J. R., Hursthouse M. B., Light M. E., Gale P. A. Chem. Eur. J., 2008, 14: 10236.

[8] Costero A. M., Sanchis J., Gil S. J. Mat. Chem., 2005, 15: 2848.

[9] Li Q., Guo Y., Xu J., Shao S. J. Sens. Actuators B, 2011, 158: 427.

[10] Bao X., Zhou Y. Sens. Actuators B, 2010, 147: 434.

[11] Anzenbacher P., Jursíková K., Sessler J. L. J. Am. Chem. Soc., 2000, 122: 9350.

[12] Qiao Y. H., Lin H., Lin H. K. Chem. Res. Chinese Universities, 2011, 27(4): 574.

[13] Matsuo S., Kiyomiya K. I., Kurebe M. Arch. Toxicol., 1998, 72: 798.

[14] Zhang S. W., Swager T. M. J. Am. Chem. Soc., 2003, 125: 3420.

[15] Cametti M., Rissanen K. Chem. Commun., 2009, 45: 2809.

[16] Wade C. R., Broomsgrove A. E. J., Aldridge S., Gabbai F. P. Chem. Rev., 2010, 110: 3958.

[17] Peng X. J., Wu Y. K., Fan J. L., Tian M. Z., Han K. J. Org. Chem., 2005, 70: 10524.

[18] Li Y., Lin H., Lin H. J. Fluores., 2010, 20: 1299.

[19] Huang W., Lin H., Cai Z. Talanta, 2010, 81: 967.

[20] Dong M., Peng Y., Dong Y. M., Tang N., Wang Y. W. Org. Lett., 2012, 14: 130.

[21] Mashraqui S. H., Ghorpade S. S., Tripathi S., Britto S. Tetrahedron Lett., 2012, 53: 765.

[22] Xu Z. C., Kim S., Kim H. N., Han S. J., Lee C., Kim J. S., Qian X. H., Yoon J. Tetrahedron Lett., 2007, 48: 9151.

[23] Nie L., Hu L., Fu X. C. Chem. J. Chinese Universities, 2011, 32(1): 56.

[24] Mahapatra A. K., Hazra G., Sahoo P. Beilstein J. Org. Chem., 2010, 6: 12.

[25] Xu D. F., Liu X. L., Lu R., Xue P. C., Zhang X. F., Zhou H. P., Jia J. H. J. Org. Biomol. Chem., 2011, 9: 1523.

[26] Fuentes de Arriba Á. L. F. L. F., Turiel M. G., Simón L., Sanz F., Boyero J. F., Muñiz F. M., Morán J. R., Alcázar V. Org. Biomol. Chem., 2011, 9: 8321.

[27] Song S. M., Ju D., Li J. F., Li D. X., Wei Y. L., Dong C., Lin P. H., Shuang S. M. Talanta, 2009, 77: 1707.

[28] Zhuang X. Q., Liu W. M., Wu J. S., Zhang H. Y., Wang P. F. Spectrochimi. Acta A, 2011, 79: 1352.

[29] Das P., Kesharwani M. K., Mandal A. K., Suresh E., Ganguly B., Das A. Org. Biomol. Chem., 2012, 10: 2263.

[30] Sun Y., Liu Y., Guo W. Sens. Actuators B, 2009, 143: 171.