Abstract
Solutions of the zwitterionic betaine dye 2,6-diphenyl-4-(2,4,6-triphenylpyridinium-1-yl)phenolate (hereinafter called standard betaine dye) and its derivatives are solvatochromic, thermochromic, piezochromic, and halochromic. That is, the position of its longest-wavelength intramolecular charge-transfer (CT) absorption band depends on solvent polarity, solution temperature, external pressure, and the type and concentration of salts (ionophores) added to the betaine dye solution. The outstanding large negative solvatochromism of this standard betaine dye has been used to establish UV/vis spectroscopically a comprehensive set of empirical parameters of solvent polarity, called ET(30) resp. ETN values, now known for many molecular and ionic solvents as well as for a great variety of solvent mixtures. This report describes relevant physicochemical properties of this standard betaine dye as well as the definition and some more recent practical applications of these solvent polarity parameters, derived from the standard betaine dye and its derivatives. In particular, the perichromism of the standard betaine dye can be used to study the polarity of microheterogeneous solutions (e.g., micelles and other organized media), surfaces (e.g., silica, alumina, cellulose), glasses (e.g., sol-gel systems), and solids (e.g., polymers), and for the construction of chemical sensors. As extension to solvatochromism, the more general term perichromism describes UV/vis band shifts of chromophore-containing solutes which are caused not only by changes in the surrounding solvent sphere, but also by their embedding in other surroundings such as micelles, vesicles, glasses, polymers, solids, interfaces, and surfaces. Some representative examples for such extended applications of the perichromic standard betaine dye are given.
Conference
International Conference on Modern Physical Chemistry for Advanced Materials (MPC '07), Kharkiv, Ukraine, 2007-06-26–2007-06-30
References
1. (a) C. Reichardt. Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim (2003; first reprint 2004), particularly Chaps. 6 and 7;Search in Google Scholar
1. (b) doi:10.1021/op0680082, C. Reichardt. Org. Process Res. Dev. 11, 105 (2007).Search in Google Scholar
2. N. G. Bakshiev (Ed.). Solvatokhromiya: Problemy i Metody, Izdatelstvo Leningradskogo Universiteta, Leningrad (1989).Search in Google Scholar
3. P. Suppan, N. Ghoneim. Solvatochromism, Royal Society of Chemistry, Cambridge (1997).Search in Google Scholar
4. E. M. Kosower, Tel Aviv University, Tel Aviv/Israel; private communication to C. R.; see also ref. [12b].Search in Google Scholar
5. W. R. Fawcett. Liquids, Solutions, and Interfaces: From Classical Macroscopic Descriptions to Modern Microscopic Details, Oxford University Press, Oxford (2004).Search in Google Scholar
6. (a) Y. Marcus. The Properties of Solvents, John Wiley, Chichester (1998);Search in Google Scholar
6. (b) Y. Marcus. Solvent Mixtures: Properties and Selective Solvation, Marcel Dekker, New York (2002).Search in Google Scholar
7. (a) doi:10.1002/ange.19650770105, C. Reichardt. Angew. Chem. 77, 30 (1965);Search in Google Scholar
7. (b) doi:10.1002/anie.196500291, C. Reichardt. Angew. Chem., Int. Ed. Engl. 4, 29 (1965);Search in Google Scholar
7. (c) doi:10.1002/ange.19790910206, C. Reichardt. Angew. Chem. 91, 119 (1979);Search in Google Scholar
7. (d) doi:10.1002/anie.197900981, C. Reichardt. Angew. Chem., Int. Ed. Engl. 18, 98 (1979).Search in Google Scholar
8. P. Muller. Pure Appl. Chem. 66, 1077 (1994); particularly p. 1151.Search in Google Scholar
9. doi:10.1021/ja01182a117, E. Grunwald, S. Winstein. J. Am. Chem. Soc. 70, 846 (1948).Search in Google Scholar
10. doi:10.1021/ja01546a020, E. M. Kosower. J. Am. Chem. Soc. 80, 3253 (1958).Search in Google Scholar
11. (a) L. P. Hammett. Physical Organic Chemistry, 2nd ed., Chap. 11, McGraw-Hill, New York (1970);Search in Google Scholar
11. (b) L. P. Hammett. Physikalische Organische Chemie, Chap. 11, Verlag Chemie, Weinheim (1973);Search in Google Scholar
11. (c) doi:10.1002/ciuz.19850190604, J. Shorter. Chem. Unserer Zeit 19, 197 (1985).Search in Google Scholar
12. (a) C. Reichardt. Chem. Soc. Rev. (London) 21, 147 (1992);10.1039/cs9922100147Search in Google Scholar
12. (b) doi:10.1021/cr00032a005, C. Reichardt. Chem. Rev. 94, 2319 (1994).Search in Google Scholar
13. (a) doi:10.1002/jlac.19636610102, K. Dimroth, C. Reichardt, Th. Siepmann, F. Bohlmann. Justus Liebigs Ann. Chem. 661, 1 (1963);Search in Google Scholar
13. (b) doi:10.1002/jlac.198319830502, C. Reichardt, E. Harbusch-Gornert. Liebigs Ann. Chem. 721 (1983);Search in Google Scholar
13. (c) doi:10.1002/jlac.199019900109, C. Reichardt, M. Eschner, G. Schafer. Liebigs Ann. Chem. 57 (1990);Search in Google Scholar
13. (d) doi:10.1002/jlac.199119910156, S. Spange, M. Lauterbach, A.-K. Gyra, C. Reichardt. Liebigs Ann. Chem. 323 (1991);Search in Google Scholar
13. (e) C. Reichardt, G. Schafer. Liebigs Ann. Chem. 1579 (1995).10.1002/jlac.1995199508219Search in Google Scholar
14. (a) C. Reichardt. Chem. Soc. Rev. (London) 21, 147 (1992);10.1039/cs9922100147Search in Google Scholar
14. (b) C. Reichardt. Solvents and Solvent Effects in Organic Chemistry, 3rd ed., cover page, Wiley-VCH, Weinheim (2003; first reprint 2004);Search in Google Scholar
14. (c) H. Langhals. GIT Fachz. Lab. 35, 766 (1991);Search in Google Scholar
14. (d) A. Streitwieser, C. H. Heathcock, E. M. Kosower. Introduction to Organic Chemistry, 4th ed., Essay 4 between pp. 621 and 622, MacMillan, New York (1992);Search in Google Scholar
14. (e) P. Rao. Resonance (Indian Academy of Sciences, Bangalore) 2, 69 (1997), title page of the May issue;Search in Google Scholar
14. (f) doi:10.1039/b402886d, N. Asaad, M. J. den Otter, J. B. F. N. Engberts. Org. Biomol. Chem. 2, 1404 (2004), Abstract.Search in Google Scholar
15. (a) D. A. Johnson, R. Shaw, E. F. Silversmith. J. Chem. Educ. 71, 517 (1994);10.1021/ed071p517.1Search in Google Scholar
15. (b) B. R. Osterby, R. D. McKelvey. J. Chem. Educ. 73, 260 (1996);10.1021/ed073p260Search in Google Scholar
15. (c) B. R. Osterby, R. D. McKelvey. J. Chem. Educ. 73, 737 (1996);10.1021/ed073p737.1Search in Google Scholar
15. (d) T. Deng, W. E. Acree Jr. J. Chem. Educ. 76, 1555 (1999);10.1021/ed076p1555Search in Google Scholar
15. (e) M. F. Vitha. J. Chem. Educ. 78, 370 (2001);10.1021/ed078p370Search in Google Scholar
15. (f) C. Machado, V. G. Machado. J. Chem. Educ. 78, 649 (2001).Search in Google Scholar
16. (a) doi:10.1002/1099-0690(200106)2001:12<2343::AID-EJOC2343>3.0.CO;2-I, C. Reichardt, D. Che, G. Heckenkemper, G. Schafer. Eur. J. Org. Chem. 2343 (2001);Search in Google Scholar
16. (b) doi:10.1002/poc.656, K. Herodes, J. Koppel, C. Reichardt, I. A. Koppel. J. Phys. Org. Chem. 16, 626 (2003);Search in Google Scholar
16. (c) doi:10.1002/poc.958, K. Herodes, I. Leito, J. Koppel, C. Reichardt, I. A. Koppel. J. Phys. Org. Chem. 18, 1013 (2005).Search in Google Scholar
17. doi:10.1002/poc.427, C. Reichardt, M. Eschner, G. Schafer. J. Phys. Org. Chem. 14, 737 (2001).Search in Google Scholar
18. (a) doi:10.1016/0009-3084(89)90025-X, M. A. Kessler, O. S. Wolfbeis. Chem. Phys. Lipids 50, 51 (1989);Search in Google Scholar
18. (b) M. A. Kessler, O. S. Wolfbeis. Chem. Abstr. 111, 59537u (1989).Search in Google Scholar
19. (a) doi:10.1351/pac198254101867, C. Reichardt. Pure Appl. Chem. 54, 1867 (1982);Search in Google Scholar
19. (b) doi:10.1351/pac199365122593, C. Reichardt, S. Asharin-Fard, A. Blum, M. Eschner, A.-M. Mehranpour, P. Milart, Th. Niem, G. Schafer, M. Wilk. Pure Appl. Chem. 65, 2593 (1993);Search in Google Scholar
19. (c) doi:10.1351/pac200476101903, C. Reichardt. Pure Appl. Chem. 76, 1903 (2004).Search in Google Scholar
20. (a) R. Allmann. Z. Kristallogr. 128, 115 (1969);10.1524/zkri.1969.128.1-2.115Search in Google Scholar
20. (b) doi:10.1016/S0022-2860(01)00640-8, K. Stadnicka, P. Milart, A. Olech, P. K. Olszewski. J. Mol. Struct. 604, 9 (2002);Search in Google Scholar
20. (c) doi:10.1016/j.molstruc.2005.08.007, L. Wojtas, P. Milart, K. Stadnicka. J. Mol. Struct. 782 157 (2006);Search in Google Scholar
20. (d) doi:10.1016/j.molstruc.2005.09.023, L. Wojtas, D. Pawlica, K. Stadnicka. J. Mol. Struct. 785, 14 (2006).Search in Google Scholar
21. (a) doi:10.1080/00268970500417994, M. Caricato, B. Mennucci, J. Tomasi. Mol. Phys. 104, 875 (2006);Search in Google Scholar
21. (b) doi:10.1021/jp047098e, A. Masternak, G. Wenska, J. Milecki, B. Skalski, St. Franzen. J. Phys. Chem. A 109, 759 (2005), particularly the Supporting Information.Search in Google Scholar
22. (a) doi:10.1021/ja001581v, M. C. Beard, G. M. Turner, C. A. Schmuttenmaer. J. Am. Chem. Soc. 122, 11541 (2000);Search in Google Scholar
22. (b) doi:10.1021/jp013603l, M. C. Beard, G. M. Turner, C. A. Schmuttenmaer. J. Phys. Chem. A 116, 878 (2002);Search in Google Scholar
22. (c) doi:10.1021/jp020579i, M. C. Beard, G. M. Turner, C. A. Schmuttenmaer. J. Phys. Chem. B 106, 106 (2002).Search in Google Scholar
23. (a) doi:10.1021/je0601560, A. Sarkar, S. Pandey. J. Chem. Eng. Data 51, 2051 (2006);Search in Google Scholar
23. (b) C. P. Fredlake, M. J. Muldoon, S. N. V. K. Aki, T. Welton, J. Brennecke. Phys. Chem. Chem. Phys. 6, 3280 (2004): ET(30) = 0.9986?ET(33) - 8.6878.Search in Google Scholar
24. (a) doi:10.1039/b500106b, C. Reichardt. Green Chem. 7, 339 (2005);Search in Google Scholar
24. (b) doi:10.1002/poc.863, C. Chiappe, D. Pieraccini. J. Phys. Org. Chem. 18, 275 (2005).Search in Google Scholar
25. doi:10.1002/poc.882, Y. Marcus. J. Phys. Org. Chem. 18, 373 (2005).Search in Google Scholar
26. M. Wu, F. Wu, H.-L. Luan, R.-J. Chen. Huaxue Xuebao (Acta Chim. Sinica) 63, 787 (2005).Search in Google Scholar
27. doi:10.1039/b616806j, D. Vinci, M. Donaldson, J. P. Hallett, E. A. John, P. Pollet, C. A. Thomas, J. D. Grilly, P. G. Jessop, C. L. Liotta, C. A. Eckert. Chem. Commun. 1427 (2007).Search in Google Scholar
28. doi:10.1021/ja971665c, G. U. Bublitz, S. G. Boxer. J. Am. Chem. Soc. 120, 3988 (1998).Search in Google Scholar
29. (a) doi:10.1021/je990212f, A. F. Lagalante, M. Spadi, T. J. Bruno. J. Chem. Eng. Data 45, 382 (2000);Search in Google Scholar
29. (b) doi:10.1039/a605521d, A. S. Labban, Y. Marcus. J. Chem. Soc., Faraday Trans. 93, 77 (1997).Search in Google Scholar
30. doi:10.1021/jp0653353, B. R. Mellein, S. N. V. K. Aki, R. L. Ladewski, J. F. Brennecke. J. Phys. Chem. B 111, 131 (2007).Search in Google Scholar
31. doi:10.1039/b507805a, N. Matsumi, A. Mori, K. Sakamoto, H. Ohno. Chem. Commun. 4557 (2005).Search in Google Scholar
32. doi:10.1021/jp0602373, A. R. Harifi-Mood, A. Habibi-Yangjeh, M. R. Gholami. J. Phys. Chem. B 110, 7073 (2006).Search in Google Scholar
33. doi:10.1021/jp057236f, C. Chiappe, D. Pieraccini. J. Phys. Chem. A 110, 4937 (2006).Search in Google Scholar
34. (a) doi:10.1016/j.supflu.2005.03.009, V. T. Wyatt, D. Bush, J. Lu, J. P. Hallett. C. L. Liotta, C. A. Eckert. J. Supercrit. Fluids 36, 16 (2005);Search in Google Scholar
34. (b) R. Eberhardt, S. Lobbecke, B. Neidhart, C. Reichardt. Liebigs Ann./Recueil 1195 (1997).10.1002/jlac.199719970622Search in Google Scholar
35. Betaine dyes 1 and 4 are commercially available by Sigma-Aldrich (1: order no. 27,244-2) and Fluka (1: order no. 43358; 4: order no. 36567).Search in Google Scholar
36. (a) doi:10.1021/jp053946+, C. Wakai, A. Oleinikova, M. Ott, H. Weingartner. J. Phys. Chem. B 109, 17028 (2005);Search in Google Scholar
36. (b) I. Krossing, J. M. Slattery, C. Daguenet, P. J. Dyson, A. Oleinikova, H. Weingartner. J. Am. Chem. Soc. 128, 13427 (2006), see Table 2.10.1021/ja0619612Search in Google Scholar
37. doi:10.1021/ar0501424, J. P. Hallett, C. L. Kitchens, R. Hernandez, C. L. Liotta, C. A. Eckert. Acc. Chem. Res. 39, 531 (2006).Search in Google Scholar
38. doi:10.1039/b400815d, C. P. Fredlake, M. J. Muldoon, S. N. V. K. Aki, T. Welton, J. F. Brennecke. Phys. Chem. Chem. Phys. 6, 3280 (2004).Search in Google Scholar
39. (a) R. E. Leitao, F. Martins, M. C. Ventura, N. Nunes. J. Phys. Org. Chem. 15, 623 (2002): MeOH/CH3CN/2-PrOH;10.1002/poc.520Search in Google Scholar
39. (b) doi:10.1016/S0009-2614(03)00319-1, C. Diaz, L. Barrio, J. Catalan. Chem. Phys. Lett. 371, 645 (2003): MeOH/EtOH/acetone;Search in Google Scholar
39. (c) K. A. Fletcher, S. Pandey. J. Phys. Chem. B 107, 13532 (2003): EtOH/H2O/[BMIm]PF6;10.1021/jp0276754Search in Google Scholar
39. (d) N. Ray, S. Bagchi. J. Phys. Chem. A 109, 142 (2005): MeOH/EtOH/H2O, MeOH/Acetone/C6H6, MeOH/CHCl3/C6H6.Search in Google Scholar
40. (a) doi:10.1007/BF00510433, K. Dimroth, C. Reichardt. Fresenius' Z. Anal. Chem. 215, 344 (1966);Search in Google Scholar
40. (b) doi:10.1007/BF00434059, Z. B. Maksimovic, C. Reichardt, A. Spiric. Z. Anal. Chem. 270, 100 (1974);Search in Google Scholar
40. (c) C. Reichardt. In Molecular Interactions, Vol. 3, p. 241ff., Table 5.4, H. Ratajczak, W. J. Orville-Thomas (Eds.) Wiley-Interscience, Chichester (1982).Search in Google Scholar
41. (a) H. Langhals. Angew. Chem. 94, 739 (1982);10.1002/ange.19820941003Search in Google Scholar
41. (b) doi:10.1002/anie.198207241, H. Langhals. Angew. Chem., Int. Ed. Engl. 21, 724 (1982);Search in Google Scholar
41. (c) H. Langhals. Nouv. J. Chim. 5, 511 (1981).Search in Google Scholar
42. K. Herodes, I. Leito, I. Koppel, M. Roses. J. Phys. Org. Chem. 12, 109 (1999): alcohols/formamides (Part 8 of a series of papers dealing with the polarity of binary solvent mixtures).10.1002/(SICI)1099-1395(199902)12:2<109::AID-POC97>3.0.CO;2-LSearch in Google Scholar
43. A. K. Laha, P. K. Das, S. Bagchi. J. Phys. Chem. A 106, 3230 (2002): EtOH/THF, EtOH/CH3CN, CH3CN/THF.10.1021/jp0121116Search in Google Scholar
44. doi:10.1039/b408052c, T. W. Bentley, I. S. Koo. Org. Biomol. Chem. 2, 2376 (2004): water/alcohol mixtures.Search in Google Scholar
45. (a) doi:10.1002/(SICI)1099-1395(200004)13:4<221::AID-POC234>3.0.CO;2-1, P. M. Mancini, C. Adam, A. del C. Perez, L. R. Vottero. J. Phys. Org. Chem. 13, 221 (2000);Search in Google Scholar
45. (b) doi:10.1002/poc.993, P. M. Mancini, L. R. Vottero. J. Phys. Org. Chem. 19, 34 (2005).Search in Google Scholar
46. (a) doi:10.1021/jp062250t, E. L. Bastos, P. L. Silva, O. A. El Seoud. J. Phys. Chem. A 110, 10287 (2006): water/alcohol mixtures;Search in Google Scholar
46. (b) doi:10.1021/jp068596l, P. L. Silva, E. L. Bastos, O. A. El Seoud. J. Phys. Chem. B 111, 6173 (2007), and refs. cited therein.Search in Google Scholar
47. doi:10.1016/j.fuel.2005.12.023, R. Budag, L. A. Giusti, V. G. Machado, C. Machado. Fuel 85, 1494 (2006).Search in Google Scholar
48. (a) doi:10.1016/0927-7757(95)03331-9, J. Kriwanek, R. Miller. Colloids Surf., A 105, 233 (1995);Search in Google Scholar
48. (b) doi:10.1016/S1010-6030(97)00166-4, P. Bilski, R. N. Holt, C. F. Chignell. J. Photochem. Photobiol. A 110, 67 (1997);Search in Google Scholar
48. (c) doi:10.1039/b310946a, J. C. Micheau, G. V. Zakharova, A. K. Chibisov. Phys. Chem. Chem. Phys. 6, 2420 (2004);Search in Google Scholar
48. (d) doi:10.1016/j.saa.2004.11.009, R. V. Pereira, M. H. Gehlen. Spectrochim. Acta A 61, 2926 (2005).Search in Google Scholar
49. doi:10.1021/ja056042a, S. Basu, D. R. Vutukuri, S. Thayumanavan. J. Am. Chem. Soc. 127, 16794 (2005).Search in Google Scholar
50. (a) doi:10.1021/ja0347383, M. T. Morgan, M. A. Carnahan, C. E. Immoos, A. A. Ribeiro, S. Finkelstein, S. J. Lee, M. W. Grinstaff. J. Am. Chem. Soc. 125, 15485 (2003);Search in Google Scholar
50. (b) doi:10.1039/b502411k, M. T. Morgan, M. A. Carnahan, S. Finkelstein, C. A. H. Prata, L. Degoricija, S. J. Lee, M. W. Grinstaff. Chem. Commun. 4309 (2005).Search in Google Scholar
51. doi:10.1039/b707719j, R. W. Sinkeldam, Y. Tor. Org. Biomol. Chem. 5, 2523 (2007).Search in Google Scholar
52. doi:10.1016/S0040-4039(00)77589-7, R. Kanski, C. J. Murray. Tetrahedron Lett. 34, 2263 (1993).Search in Google Scholar
53. doi:10.1039/b419246j, C. G. Venturini, J. Andreaus, V. G. Machado, C. Machado. Org. Biomol. Chem. 3, 1751 (2005).Search in Google Scholar
54. (a) doi:10.1016/S0927-7757(02)00022-5, N. O. Mchedlov-Petrossyan, N. A. Vodolazkaya, C. Reichardt. Colloids Surf., A 205, 215 (2002);Search in Google Scholar
54. (b) doi:10.1021/la0401361, N. O. Mchedlov-Petrossyan, N. A. Vodolazkaya, A. A. Kornienko, E. L. Karyakina, C. Reichardt. Langmuir 21, 7090 (2005).Search in Google Scholar
55. E. B. Tada, L. P. Novaki, O. A. El Seoud. Langmuir 17, 652 (2001) and refs. cited therein.10.1021/la001135lSearch in Google Scholar
56. E. Fuguet, C. Rafols, E. Bosch, M. Roses. Langmuir 19, 55 (2003) and refs. cited therein.10.1021/la026307oSearch in Google Scholar
57. (a) A. R. Ibragimova, F. G. Valeeva, L. Ya. Zakharova, L. A. Kudryavtseva, N. M. Azancheev, S. N. Shtykov, L. S. Shtykova, I. V. Bogomolova. Zh. Fiz. Khim. 78, 1186 (2004);Search in Google Scholar
57. (b) A. R. Ibragimova, F. G. Valeeva, L. Ya. Zakharova, L. A. Kudryavtseva, N. M. Azancheev, S. N. Shtykov, L. S. Shtykova, I. V. Bogomolova. Russ. J. Phys. Chem. 78, 1027 (2004);Search in Google Scholar
57. (c) doi:10.1016/j.molliq.2004.07.079, L. Ya. Zakharova, A. R. Ibragimova, F. G. Valeeva, L. A. Kudryavtseva, A. I. Konovalov, S. N. Shtykov, L. S. Shtykova, I. V. Bogomolova. J. Mol. Liq. 116, 83 (2005).Search in Google Scholar
58. doi:10.1080/00319100500038686, M. O. Iwunze. Phys. Chem. Liq. 43, 195 (2005).Search in Google Scholar
59. (a) N. O. Mchedlov-Petrossyan, Yu. V. Isaenko, S. T. Goga. Zh. Obshch. Khim. 74, 1871 (2004);10.1007/s11176-005-0093-5Search in Google Scholar
59. (b) doi:10.1007/s11176-005-0093-5, N. O. Mchedlov-Petrossyan, Yu. V. Isaenko, S. T. Goga. Russ. J. Gen. Chem. 74, 1741 (2004).Search in Google Scholar
60. doi:10.1021/ja027772a, J. E. Klijn, J. B. F. N. Engberts. J. Am. Chem. Soc. 125, 1825 (2003).Search in Google Scholar
61. doi:10.1081/DIS-200049634, S. Pandey. J. Dispersion Sci. Technol. 26, 381 (2005).Search in Google Scholar
62. (a) doi:10.1021/jo0617971, E. V. Anslyn. J. Org. Chem. 72, 687 (2007);Search in Google Scholar
62. (b) P. Grundler. Chemical Sensors. An Introduction for Scientists and Engineers, Springer, Berlin (2007).Search in Google Scholar
63. (a) doi:10.1016/0039-9140(92)80202-O, Y. Sadaoka, Y. Sakai, Y. Murata. Talanta 39, 1675 (1992);Search in Google Scholar
63. (b) T. Sadaoka, M. Matsuguchi, Y. Sakai, Y. Murata. Chem. Lett. (Tokyo) 53 (1992).10.1246/cl.1992.53Search in Google Scholar
64. (a) doi:10.1002/adma.19950071109, C. Hubert, D. Fichou, F. Garnier. Adv. Mater. 7, 914 (1995);Search in Google Scholar
64. (b) doi:10.1016/0032-3861(95)91215-S, C. Hubert, D. Fichou, P. Valat, F. Garnier, B. Villeret. Polymer 36, 2663 (1995).Search in Google Scholar
65. doi:10.1039/c39950002445, D. Crowther, X. Liu. J. Chem. Soc., Chem. Commun. 2445 (1995).Search in Google Scholar
66. doi:10.1021/la960517h, C. Rottman, G. S. Grader, Y. De Hazan, D. Avnir. Langmuir 12, 5505 (1996).Search in Google Scholar
67. doi:10.1016/S0003-2670(96)00495-3, J. H. Krech, S. L. Rose-Pehrsson. Anal. Chim. Acta 341, 53 (1997).Search in Google Scholar
68. F. L. Dickert, U. Geiger, P. Lieberzeit, U. Reutner. Sens. Actuators, B 70, 263 (2000).10.1016/S0925-4005(00)00578-5Search in Google Scholar
69. doi:10.1016/S0003-2670(00)01363-5, P. Blum, G. J. Mohr, K. Matern, J. Reichert, U. E. Spichiger-Keller. Anal. Chim. Acta 432, 269 (2001).Search in Google Scholar
70. (a) S. Fiorilli, B. Onida, D. Macquarrie, E. Garrone. Sens. Actuators, B 100, 103 (2004);10.1016/j.snb.2003.12.031Search in Google Scholar
70. (b) doi:10.1021/la062829i, S. Fiorilli, B. Onida, C. Barolo, G. Viscardi, D. Brunel, E. Garrone. Langmuir 23, 2261 (2007).Search in Google Scholar
71. M. Kleemann, A. Suisalu, J. Kikas. Proc. SPIE-Opt. Mater. Appl. 5946, 59460N-1 (2005).Search in Google Scholar
72. M. C. Burt, B. C. Dave. Sens. Actuators, B 107, 552 (2005).10.1016/j.snb.2004.11.015Search in Google Scholar
73. (a) doi:10.1021/ja052606z, C. Zhang, K. S. Suslick. J. Am. Chem. Soc. 127, 11548 (2005);Search in Google Scholar
73. (b) K. S. Suslick, N. A. Rakow, A. Sen. Tetrahedron 60, 11133 (2004);10.1016/j.tet.2004.09.007Search in Google Scholar
73. (c) doi:10.1590/S0100-40422007000300029, K. S. Suslick, D. P. Bailey, C. K. Ingison, M. Janzen, M. E. Kosal, W. B. McNamara, N. R. Rakov, A. Sen, J. J. Weaver, J. B. Wilson, C. Zhang, S. Nakagaki. Quim. Nova 30, 677 (2007).Search in Google Scholar
74. doi:10.1016/j.tetlet.2006.10.109, D. C. Reis, C. Machado, V. G. Machado. Tetrahedron Lett. 47, 9339 (2006).Search in Google Scholar
75. doi:10.1021/ja068959v, C. Koopmans, H. Ritter. J. Am. Chem. Soc. 129, 3502 (2007); the polymer-bound solvatochromic pyridinium-phenolate dye described in this paper is in fact not "Reichardt's dye" but is rather "Brooker's merocyanine dye".Search in Google Scholar
76. doi:10.1002/jlac.19636690111, K. Dimroth, C. Reichardt, A. Schweig. Justus Liebigs Ann. Chem. 669, 95 (1963).Search in Google Scholar
77. doi:10.1021/jp012699g, X. H. Zhao, J. A. Burt, F. J. Knorr, J. L. McHale. J. Phys. Chem. A 105, 11110 (2001).Search in Google Scholar
78. (a) doi:10.1002/jlac.199319930106, C. Reichardt, S. Asharin-Fard, G. Schafer. Liebigs Ann. Chem. 23 (1993);Search in Google Scholar
78. (b) doi:10.1002/cber.19931260122, C. Reichardt, S. Asharin-Fard, G. Schafer. Chem. Ber. 126, 143 (1993).Search in Google Scholar
79. (a) V. G. Machado, C. Machado, M. G. Nascimento, M. C. Rezende. Quim. Nova 19, 523 (1996);Search in Google Scholar
79. (b) V. G. Machado, C. Machado, M. G. Nascimento, M. C. Rezende. Chem. Abstr. 126, 226509e (1997).Search in Google Scholar
80. C. Reichardt, A. Blum, K. Harms, G. Schafer. Liebigs Ann./Recueil 707 (1997).10.1002/jlac.199719970411Search in Google Scholar
81. K. Tamura, Y. Ogo, T. Imoto. Chem. Lett. (Tokyo) 625 (1973).10.1246/cl.1973.625Search in Google Scholar
82. doi:10.1021/j100346a025, W. S. Hammack, D. N. Hendrickson, H. G. Drickamer. J. Phys. Chem. 93, 3483 (1989).Search in Google Scholar
83. I. Jano. J. Chim. Phys. Phys.-Chim. Biol. 89, 1951 (1992).10.1051/jcp/1992891951Search in Google Scholar
84. C. Streck, R. Richert. Ber. Bunsenges. Phys. Chem. 98, 619 (1994).Search in Google Scholar
85. H. C. Andersen. Complete Fairy Tales and Stories, translated by E. Haugard, Gollantz, London (1974).Search in Google Scholar
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