Colorimetric "naked eye" detection of CN-, F-, CH3COO- and H2PO4- ions by highly nonplanar electron deficient perhaloporphyrins

RSC Advances

Volumn 5, Issue 5, 2015, Pages 3269-3275

  Chaudhri, Nivedita ^a   Sankar, Muniappan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COLORIMETRY;

ACID TREATMENTS; ELECTROCHEMICAL REDOX; ELECTROCHEMICAL STUDIES; ELECTRON-DEFICIENT; HOST GUEST COMPLEXES; NANOMOLAR CONCENTRATION; SENSING ABILITIES; SPECTROSCOPIC TECHNIQUE;

NEGATIVE IONS;

EID: 84918819356     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra11368c     Document Type: Article

References (67)

1. (a) L. R. Milgrom, The Colours of Life: An Introduction to the Chemistry of Porphyrins and Related Compounds, Oxford University Press, New York, 1997;
2. (b) J. A. Shelnutt, X.-Z. Song, J.-G. Ma, S.-L. Jia, W. Jentzen and C. J. Medforth, Chem. Soc. Rev., 1998, 27, 31;
3. (c) M. O. Senge, The Porphyrin Handbook, ed. K. M. Kadish, K. M. Smith and R. Guilard, Academic Press, San Diego, 2000, vol. 1, p. 239;
4. (d) M. O. Senge, Chem. Commun., 2006, 243.
5. (a) D. S. Kim and J. L. Sessler, Chem. Soc. Rev., 2014, DOI: 10.1039/c4cs00157e;
6. (b) V. V. Roznyatovskiy, C.-H. Lee and J. L. Sessler, Chem. Soc. Rev., 2013, 42, 1921;
7. (c) P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed., 2001, 40, 486;
8. (d) E. Matthews and P. D. Beer, Supramol. Chem., 2005, 17, 411.
9. (a) A. Bianchi, K. Bowman-James and E. Garcia-Espana, Supra-molecular Chemistry of Anions, Wiley-VCH, New York, 1997;
10. (b) J. L. Sessler, P. A. Gale and W.-S. Cho, Anion Receptor Chemistry, RSC Publishing, Cambridge, UK, 2006;
11. (c) L. C. Gilday, N. G. White and P. D. Beer, Dalton Trans., 2012, 41, 7092.
12. (a) P. D. Beer and P. A. Gale, Angew. Chem., 2001, 113, 502;
13. (b) E. Matthews and P. D. Beer, Supramol. Chem., 2005, 17, 411.
14. (a) B. Vennesland, E. E. Comm, C. J. Knownles, J. Westly and F. Wissing, Cyanide in Biology, Academic press, London, 1981;
15. (b) M. S. Frant and J. Ross, Science, 1966, 154, 1533;
16. (c) D. Briancon, Rev. Rheum., 1997, 64, 78.
17. (a) R. L. P. Adams, J. T. Knowler and D. P. Leader, The Biochemistry of the Nucleic Acids, ed. Chapman and Hall, New York, 11th edn, 1992;
18. (b) X. F. Shang and X. F. Xu, BioSystems, 2009, 96, 165.
19. (a) C.-H. Lee, H. Miyaji, D.-W. Yoon and J. L. Sessler, Chem. Commun., 2008, 24;
20. (b) S. K. Kim and J. L. Sessler, Acc. Chem. Res., 2014, 47, 2525;
21. (c) P. Anzenbacher, R. Nishiyabu and M. A. Palacois, Coord. Chem. Rev., 2006, 250, 2929;
22. (d) P. A. Gale and C.-H. Lee, Top. Heterocycl. Chem., 2010, 24, 39.
23. (a) A. J. Pistner, D. A. Lutterman, M. J. Ghidiu, Y.-Z. Ma and J. Rosenthal, J. Am. Chem. Soc., 2013, 135, 6601;
24. (b) C. I. M. Santos, E. Oliveira, J. F. B. Barata, M. A. F. Faustino, J. A. S. Cavaleiro, M. G. Neves and C. Lodeiro, J. Mater. Chem., 2012, 22, 13811;
25. (c) P. Yadav and M. Sankar, Dalton Trans., 2014, 43, 14680;
26. (d) J. L. Sessler and J. M. Davis, Acc. Chem. Res., 2001, 34, 989;
27. (e) D. G. Cho, Syntheses and studies of sapphyrins and anion receptors, Umi Dissertation Publishing, 2012;
28. (f) D. H. Won, M. Toganoh, H. Uno and H. Furuta, Dalton Trans., 2009, 6151;
29. (g) Y. Xie, T. Marimoto and H. Furuta, Angew. Chem., Int. Ed., 2006, 45, 6907;
30. (h) F. D'Souza, N. K. Subbaiyan, Y. Xie, J. P. Hill, K. Ariga, K. Ohkubo and S. Fukuzumi, J. Am. Chem. Soc., 2009, 131, 16138;
31. (i) J. P. Hill, A. L. Schumacher, F. D'Souza, J. Labuta, C. Redshaw, M. R. J. Elsegood, M. Aoyagi, T. Nakanishi and K. Ariga, Inorg. Chem., 2006, 45, 8288;
32. (j) M. Takeuci, T. Shioya and T. M. Swager, Angew. Chem., Int. Ed., 2001, 40, 3372.
33. (a) D. P. Cormode, M. G. B. Drew, R. Jagessar and P. D. Beer, Dalton Trans., 2008, 6732;
34. (b) P. D. Beer, D. P. Cormode and J. J. Davis, Chem. Commun., 2004, 414;
35. (c) J. M. M. Rodrigues, A. S. Farinha, P. V. Muteto, S. M. Woranovicz-Barreira, F. A. A. Paz, M. G. Neves, J. A. S. Cavaleiro, A. C. Tome, M. T. Gomes, J. L. Sessler and J. P. C. Tome, Chem. Commun., 2014, 50, 1359.
36. (a) R. Harada and T. Kojima, Chem. Commun., 2005, 716;
37. (b) T. Honda, T. Kojima and S. Fukuzumi, Chem. Commun., 2009, 4994;
38. (c) M. M. Kruk, A. S. Starukhina, N. Zh. Mamardashvilib, G. M. Mamardashvilib, Y. B. Ivanovab and O. V. Maltsevab, J. Porphyrins Phthalocyanines, 2009, 13, 1148.
39. (a) N. Agarwal and M. Ravikanth, Tetrahedron, 2004, 60, 4739;
40. (b) M. O. Senge, T. P. Forsyth, L. T. Nguyen and K. M. Smith, Angew. Chem., Int. Ed. Engl., 1994, 30, 2485;
41. (c) N. Agarwal, C.-H. Hung and M. Ravikanth, Tetrahedron, 2004, 60, 10671.
42. (a) S.-J. Hong, J. Yoo, S.-H. Kim, J. S. Kim, J. Yoon and C.-H. Lee, Chem. Commun., 2009, 189;
43. (b) M. G. D. Holaday, G. Tarafdar, B. Adinarayana, M. L. P. Reddy and A. Srinivasan, Chem. Commun., 2014, 50, 10834;
44. (c) E. Palomares, M. V. Martinez-Diaz, T. Torres and E. Coronado, Adv. Funct. Mater., 2006, 16, 1166;
45. (d) Y.-H. Kim and J.-I. Hong, Chem. Commun., 2002, 512;
46. (e) L. D. Chen, X. U. Zou and P. Bühlmann, Anal. Chem., 2012, 84, 9192.
47. (a) V. Amendola, D. Esteban-Gomez, L. Fabbrizzi and M. Licchelli, Acc. Chem. Res., 2006, 39, 343;
48. (b) A. Basu, S. K. Dey and G. Das, RSC Adv., 2013, 3, 6596;
49. (c) Q. Wang, Y. Xie, Y. Ding, X. Li and W. Zhu, Chem. Commun., 2010, 46, 3669;
50. (d) G. Lu, X. Zhang, X. Cal, Y. Fang, M. Zhu, W. Zhu, Z. Ou and K. M. Kadish, J. Porphyrins Phthalocyanines, 2013, 17, 941;
51. (e) Y. Fang, P. Bhyrappa, Z. Ou and K. M. Kadish, Chem.-Eur. J., 2014, 20, 524.
52. (a) P. Bhyrappa and V. Krishnan, Inorg. Chem., 1991, 30, 239;
53. (b) P. Bhyrappa and P. Bhavana, J. Chem. Soc., Perkin Trans. 2, 2001, 238.
54. (a) M. O. Senge, V. Gerstung, K. Ruhlandt-Senge, S. Runge and I. Lehmann, J. Chem. Soc., Dalton Trans., 1998, 4187;
55. (b) L. Jaquinod, R. G. Khoury, K. M. Shea and K. M. Smith, Tetrahedron, 1999, 5, 13151;
56. (c) P. Bhyrappa, M. Sankar and B. Varghese, Inorg. Chem., 2006, 45, 4136.
57. (a) T. Wijesekera, A. Matsumoto, D. Dolphin and D. Lexa, Angew. Chem., Int. Ed. Engl., 1990, 29, 1028;
58. (b) P. Bhyrappa and V. Krishnan, Chem. Lett., 1993, 869.
59. K. M. Kadish, G. Royal, E. V. Caemelbecke and L. Gueletti, The Porphyrin Handbook, ed. K. M. Kadish, K. M. Smith and R. Guilard, Academic Press, San Diego, 2000, vol. 9, p. 1.
60. (a) A. V. Hill, J. Physiol., 1910, 40, IV-VII;
61. (b) A. Pfeil and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1992, 838.
62. (a) P. Bhyrappa and P. Bhavana, Chem. Phys. Lett., 2001, 342, 39;
63. (b) P. Bhyrappa and P. Bhavana, Chem. Phys. Lett., 2002, 357, 108.
64. A. S. F. Farinha, M. J. F. Calvete, F. A. A. Paz, A. C. Tome, J. A. S. Cavaleiro, J. L. Sessler and J. P. C. Tome, Sens. Actuators, B, 2014, 201, 387.
65. V. M. Patel, J. A. Patel, S. S. Havele and S. R. Dhaneshwar, Int. J. ChemTech Res., 2010, 2, 756-761.
66. A. Giraudeau, H. J. Callot and M. Gross, Inorg. Chem., 1979, 18, 201.
67. G. A. Spyroulias, A. P. Despotopoulos, C. P. Raptopoulou, A. Terzis, D. de Montauzon, R. Poilblanc and A. G. Coutsolelos, Inorg. Chem., 2002, 41, 2648.