Effect of alkali on methylene blue (C.I. Basic Blue 9) and other thiazine dyes

Dyes and Pigments

Volumn 88, Issue 2, 2011, Pages 149-155

  Mills, Andrew ^a   Hazafy, David ^a   Parkinson, John ^a   Tuttle, Tell ^a   Hutchings, Michael G ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

C.I. Basic Blue 9; DFT; Hydrolysis; Methylene blue; Methylene violet; Thiazine

Indexed keywords

C.I. BASIC BLUE; DFT; METHYLENE BLUE; METHYLENE VIOLET; THIAZINE;

CHROMATOGRAPHIC ANALYSIS; THIN LAYER CHROMATOGRAPHY;

HYDROLYSIS;

EID: 77956422353     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2010.05.015     Document Type: Article

References (49)

1. A.S. Travis The rainbow makers 1993 Associated University Presses London
2. The merck index 1989 Merck & Co., Inc. Rahway
3. http://en.wikipedia.org/wiki/Methylene-blue accessed 01 2010.
4. A.D. Murray, R.T. Stuff, T.S. Ahearn, P. Bentham, K.M. Seng, and C. Wischik Alzheimer's Demen 4 2008 T786
5. Wischik CM, Rickard JE, Harrington CR, Horsley D, Storey JMD, Marshall C, Sinclair JP, Tan HW. Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride, U.S. patent 2006/0287523 A1 published Dec 21st 2006.
6. http://www.examiner.com/x-11432-Pittsburgh-Medical-Technology- Examiner∼y2010m1d9-Mehtylene-blue-may-hold-the-cure-for-neurodegenerative- diseases-such-as-Alzheimers-disease?cid=edition-rss-Pittsburgh January 09 2010
7. S. Basu, S. Panigrahi, S. Praharaj, S.K. Ghosh, S. Pande, and S. Jana J Phys Chem A 111 2007 578
8. T.V. Thien [chapter 3] R. Muthyala, Chemistry and applications of leuco dyes 1997 Plenum Press New York 67
9. L. Adamcikova, K. Pavlikova, and P. Sevcik React Kinet Catal Lett 69 2000 91
10. W.C. Holmes, and R.W. French Stain Technol 1 1926 17
11. W.J. MacNeal, and J.A. Killian J Am Chem Soc 48 1926 740
12. A. Mills, D. Hazafy, J.A. Parkinson, T. Tuttle, and M.G. Hutchings J Phys Chem A 113 2009 9575 9576
13. T. Pal J Phys Chem A 113 2009 9577
14. M.J. Plater ARKIVOC 2003 37 42
15. P.N. Marshall, and S.M. Lewis Stain Technol 50 1976 375
16. V. Barone, and M. Cossi J Phys Chem A 102 1998 1995
17. M. Cossi, N. Rega, G. Scalmani, and V. Barone J Comput Chem 24 2003 669
18. A.D. Becke Phys Rev A 38 1988 3098
19. A.D. Becke J Chem Phys 98 1993 5648
20. R.H. Hertwig, and W. Koch Chem Phys Lett 268 1997 345
21. C.T. Lee, W.T. Yang, and R.G. Parr Phys Rev B 37 1988 785
22. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch J Phys Chem 98 1994 11623
23. S.H. Vosko, L. Wilk, and M. Nusair Can J Phys 58 1980 1200
24. P.C. Hariharan, and J.A. Pople Theor Chim Acta 28 1973 213
25. R. Krishnan, J.S. Binkley, R. Seeger, and J.A. Pople J Chem Phys 72 1980 650
26. R. Bauernschmitt, and R. Ahlrichs Chem Phys Lett 256 1996 454
27. M.E. Casida, C. Jamorski, K.C. Casida, and D.R. Salahub J Chem Phys 108 1998 4439
28. R.E. Stratmann, G.E. Scuseria, and M.J. Frisch J Chem Phys 109 1998 8218
29. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 03, revision E.04 2004 Gaussian, Inc. Wallingford CT
30. A. Reed, R.B. Weinstock, and F. Weinhold J Chem Phys 83 1985 735
31. D.C. Abbott Analyst 87 1962 286
32. W.C. Holmes, and E.F. Snyder Stain Technol 4 1929 7
33. R. Bonneau, J. Faure, and J. Joussot-Dubien Talanta 14 1967 121
34. The discoverer's name is frequently appended when naming the thiazine-based Methylene Violet, to distinguish it from other species with the same or similar name e.g. Methylene Violet 3RAX, which has an unrelated safranine structure, 3-amino-7-(diethylamino)-5-phenyl phenazinium chloride; see Aldrich Catalogue 307505.
35. S. Otsuki, and T. Taguchi Bull Chem Soc Jpn 69 1996 2525
36. Plater MJ. Private communication, February 2010.
37. Mills A, Hazafy D. unpublished results.
38. P.N. Marshall, and S.M. Lewis Biotech Histochem 50 1975 375 381
39. G.N. Lewis, O. Goldschmid, T.T. Magel, and J. Bigeleisen J Am Chem Soc 65 1953 1150
40. A recent paper examines the use TD DFT calculations of excitation energies of dyes, including MB Fabian J Dyes Pigm 84 2010 36 53
41. Beilstein database v.2008/04, via CrossFire Commander v.7.1, Elsevier Information Systems.
42. H. Nishikiori, S. Nagaya, N. Tanaka, A. Katsuki, and T. Fujii Bull Chem Soc Jpn 72 1999 915 921
43. G.N. Lewis, and J. Bigeleisen J Am Chem Soc 65 1943 1144 1150
44. D.E. Falvey J Phys Org Chem 12 1999 589 596
45. J. Griffiths, and R. Cox Dyes Pigm 42 1999 29 34
46. R. Möhlau Ber Deutschen Chem Ges 18 1884 2915
47. Unpublished results.
48. H. Zollinger Color chemistry [chapter 4] 3rd ed. 2003 Vhca and Wiley-VCH Zürich
49. V.E. Nicotra, M.F. Mora, R.A. Iglesias, and A.M. Baruzzi Dyes Pigm 76 2008 315