Anion Recognition of Two Calix[4]pyrrole-BODIPY Sensors Containing Different Steric Groups

Yongjun Lv; Wei Wei; Yuntao Xie

doi:10.14233/ajchem.2014.17762

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Issue Published : November 6, 2014

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

Anion Recognition of Two Calix[4]pyrrole-BODIPY Sensors Containing Different Steric Groups

https://doi.org/10.14233/ajchem.2014.17762

Yongjun Lv

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

Wei Wei

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

Yuntao Xie

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

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22
Article Published : November 6, 2014

Abstract

The anion recognition properties of meso-octaethyl and meso-tetracyclohexyl calix[4]pyrrole-based boradiazaindacenes (BODIPY) sensors (compound 2 and 3) were investigated by absorption and fluorescence spectra. The results showed that both sensors effectively gave dual responses for F^– through color changes and fluorescence quenching. Compared with meso-octamethylcalix[4]pyrrole-BODIPY sensor compounds 1, 2 exhibited a higher selectivity for F^– and compound 3 showed rather weaker bonding interactions with tested anions, which can be ascribed to their steric hindrance effect of different meso-alkyl groups of calix[4]pyrrole.

Keywords

Anion recognition Calix[4]pyrrole BODIPY Steric

Lv, Y., Wei, W., & Xie, Y. (2014). Anion Recognition of Two Calix[4]pyrrole-BODIPY Sensors Containing Different Steric Groups. Asian Journal of Chemistry, 26(22), 7763–7765. https://doi.org/10.14233/ajchem.2014.17762

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References

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References

L.E. Santos-Figueroa, M.E. Moragues, E. Climent, A. Agostini, R. Martínez-Máñez and F. Sancenón, Chem. Soc. Rev., 42, 3489 (2013); doi:10.1039/c3cs35429f.

L. Fabbrizzi and A. Poggi, Chem. Soc. Rev., 42, 1681 (2013); doi:10.1039/c2cs35290g.

H.X. Ren, A.H. Zhang and Y.J. Wang, Asian J. Chem., 26, 273 (2014); doi:10.14233/ajchem.2014.15886.

M. Wenzel, J.R. Hiscock and P.A. Gale, Chem. Soc. Rev., 41, 480 (2011); doi:10.1039/c1cs15257b.

C. Caltagirone and P.A. Gale, Chem. Soc. Rev., 38, 520 (2009); doi:10.1039/b806422a.

S. Ashour, Asian J. Chem., 12, 32 (2000).

C.H. Lee, H. Miyaji, D.W. Yoon and J.L. Sessler, Chem. Commun., 24 (2007); doi:10.1039/b713183f.

P.A. Gale, J.P. Anzenbacher and J.L. Sessler, Coord. Chem. Rev., 222, 57 (2001); doi:10.1016/S0010-8545(01)00346-0.

P.A. Gale, J.L. Sessler and V. Král, Chem. Commun., 1 (1998); doi:10.1039/a706280j.

P.A. Gale, J.L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 118, 5140 (1996); doi:10.1021/ja960307r.

C.N. Warriner, P.A. Gale, M.E. Light and M.B. Hursthouse, Chem. Commun., 1810 (2003); doi:10.1039/b303959e.

G. Cafeo, F.H. Kohnke, G.L. La Torre, A.J.P. White and D.J. Williams, Chem. Commun., 1207 (2000); doi:10.1039/B002239J.

H. Miyaji, W. Sato and J.L. Sessler, Angew. Chem. Int. Ed., 39, 1777 (2000); doi:10.1002/(SICI)1521-3773(20000515)39:10<1777::AID-ANIE1777>3.0.CO;2-E.

H. Miyaji, J.P. Anzenbacher Jr., J.L. Sessler, E.R. Bleasdale and P.A. Gale, Chem. Commun., 1723 (1999); doi:10.1039/a905054j.

W.E. Allen, P.A. Gale, C.T. Brown, V.M. Lynch and J.L. Sessler, J. Am. Chem. Soc., 118, 12471 (1996); doi:10.1021/ja9632217.

K. Liu, J. Xu, Y. Sun, Y. Guo, S.X. Jiang and S.J. Shao, Spectrochim. Acta A, 69, 1201 (2008); doi:10.1016/j.saa.2007.06.027.

N. Boens, V. Leen and W. Dehaen, Chem. Soc. Rev., 41, 1130 (2012); doi:10.1039/c1cs15132k.

G. Ulrich, R. Ziessel and A. Harriman, Angew. Chem. Int. Ed., 47, 1184 (2008); doi:10.1002/anie.200702070.

Y.J. Lv, J. Xu, Y. Guo and S.J. Shao, J. Incl. Phenom. Macrocycl. Chem., 72, 95 (2012); doi:10.1007/s10847-011-9946-1.

M. Kollmannsberger, K. Rurack, U. Resch-Genger and J. Daub, J. Phys. Chem. A, 102, 10211 (1998); doi:10.1021/jp982701c.

K.A. Conners, Binding Constants: The Measurement of Molecular Complex Stability, John Wiley, New York, pp. 4/147-4/149 (1987).

P.A. Gale, J.L. Sessler, W.E. Allen, N.A. Tvermoes and V. Lynch, Chem. Commun., 665 (1997); doi:10.1039/a700685c.

R. Martínez-Máñez and F. Sancenón, Chem. Rev., 103, 4419 (2003); doi:10.1021/cr010421e.

B. Valeur, Molecular Fluorescence, Principles and Applications, Wiley-VCH, New York, USA, pp. 3/57-3/59 (2002).

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Anion Recognition of Two Calix[4]pyrrole-BODIPY Sensors Containing Different Steric Groups

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