Azonium-ammonium tautomerism and inclusion complexation of 1-(2,4-diamino phenylazo) naphthalene and 4-aminoazobenzene

Journal of Fluorescence

Volumn 21, Issue 4, 2011, Pages 1485-1497

  Venkatesh, G ^a   Prabhu, A Antony Muthu ^a   Rajendiran, N ^a  

^a ANNAMALAI UNIVERSITY   (India)

Author keywords

cyclodextrin; Fat brown RR; Inclusion complex; pH effect; Solvent; Tautomerism

Indexed keywords

ACID SOLUTIONS; AMINO GROUP; AZO TAUTOMER; BATHOCHROMIC SHIFT; EMISSION MAXIMA; FAT BROWN RR; HYPSOCHROMIC SHIFTS; INCLUSION COMPLEX; INCLUSION COMPLEXATION; NAPHTHALENE RING; RED SHIFT; RED-SHIFTED; SPECTRAL CHARACTERISTICS; TAUTOMERISM; UV-VISIBLE;

AMMONIUM COMPOUNDS; HYDROGEN; PH EFFECTS; SOLVENTS;

NAPHTHALENE;

1 (2,4 DIAMINO PHENYLAZO)NAPHTHALENE; 1-(2,4-DIAMINO PHENYLAZO)NAPHTHALENE; 4 AMINOAZOBENZENE; AZO COMPOUND; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; NAPHTHALENE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CHEMISTRY; FLUORESCENCE; PH; QUANTUM THEORY; THERMODYNAMICS;

AZO COMPOUNDS; BETA-CYCLODEXTRINS; FLUORESCENCE; HYDROGEN-ION CONCENTRATION; NAPHTHALENES; P-AMINOAZOBENZENE; QUANTUM THEORY; QUATERNARY AMMONIUM COMPOUNDS; THERMODYNAMICS;

EID: 80053442054     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-011-0835-1     Document Type: Article

References (66)

1. Okada M, Harada A (2004) Org Lett 6:361
2. Terao J, Tang A, Michels JJ, Krivokapic A, Anderson HL (2004) Chem Commun 56
3. Look JS, May BL, Clements P, Lincoln SF, Easton CJ (2004) Org Biomol Chem 2:337
4. Liu Y, Zhao YL, Zhang HY, Li XY, Liang P, Zhang XZ, Xu JJ (2004) Macromolecules 37:6362
5. Wang QC, Qu DH, Ren J, Chen K, Tian H (2004) Angew Chem Int Ed 43:2661
6. Saito M, Shimomura T, Okumura Y, Ito J, Hayakawa R (2001) J Chem Phys 114:1
7. Liu Y, Zhao YL, Zhang HY, Song HB (2003) Angew Chem Int Ed 42:3260
8. Szejtli J, Osa T (1996) In: Atwood JL, Daves JE, MacNicol DD, Vogtle F (eds) Comprehensive supramolecular chemistry, vol III. Pergamon/Elsevier, Oxford
9. Liu Y, Wang H, Liang P, Zhang HY (2004) Angew Chem Int Ed 43:2690
10. Mulder A, Jukovic A, Huskens J, Reinhoudt DN (2004) Org Biomol Chem 2:1748
11. Meo PL, D'Anna F, Riela S, Gruttadauria M (2003) Org Biomol Chem 1:1584
12. Agbaria RA, Butterfield MT, Warner IM (1996) J Phys Chem 100:17133
13. Dyck ASM, Kisiel U, Bohne C (2003) J Phys Chem B 107:11652
14. Craig MR, Hutchings MG, Claridge TDW (2001) Angew Chem Int Ed 40:1071
15. Takei M, Yui H, Hirose Y, Sawada T (2001) J Phys Chem A 105:11395
16. Bortolus P, Monti S (1987) J Phys Chem 91:5046
17. Sanchez AM, de Rossi RH (1996) J Org Chem 61:3446
18. Abou-Hamdan A, Bugnon P, Saudan C, Lye PG, Merbach AE (2000) J Am Chem Soc 122:592
19. Harata K (2003) Carbohydr Res 338:353
20. Udachin KA, Wilson LD, Ripmeester JA (2000) J Am Chem Soc 122:12375
21. Kamitori S, Matsuzaka O, Kondo S, Muraoka S, Okuyama K, Nohuchi K, Okada M, Harada A (2000) Macromolecules 33:1500
22. Liu Y, Zhao YL, Zhang HY, Yang EC, Guan XD (2004) J Org Chem 69:3383
23. Fabian J, Hartmann H (1980) Light absorption of organic colorants, in reactivity and structure concepts in orgnic chemistry, vol. 12. Springer, Berlin
24. Mohr GJ, Wolfbeis OS (1994) Anal Chim Acta 292:41
25. Jorgenson MJ, Hartter DA (1963) J Am Chem Soc 85:878
26. Yagil G (1967) J Phys Chem 71:1045
27. Zollinger H (1991) Color chemistry: syntheses, properties and applications of organic dyes and pigments. VCH, Weinheim
28. Joshi H, Kamounah FS, van der Zwan G, Gooijer C, Antonov L (2001) J Chem Soc Perkin Trans 2:2303
29. Antonov L, Fabian WMF, Nedeltcheva D, Kamounah FS (2002) J Chem Soc Perkin Trans 2:1173
30. Antonov L, Stoyanov S, Stoyanova T (1994) Dyes Pigm 26:149
31. Antonov L, Stoyanov S (1995) Dyes Pigm 28:31
32. Smoluch M, Joshi H, Gerssen A, Gooijer C, van der Zwan G (2005) J Phys Chem A 109:535
33. Zhu A, Wang B, White JO, Drickamer HG (2004) J Phys Chem B 108:891
34. Alarcón SH, Olivieri AC, Labadie GR, Cravero RM, Gonzales- Sierra M (1995) Tetrahedron 51:4619
35. Reichardt C, Dimorth K (1968) Fortschr Chem Forsch 11:1
36. Biolet L, Kawaski A (1962) Z Naturforsch 179:621
37. Lippert E (1955) Z Naturforsch 18A:541
38. Rajendiran N, Swaminathan M (1996) Bull Chem Soc Jpn 69:2447
39. Rajendiran N, Swaminathan M (1995) J Photochem Photobiol A Chem 90:109
40. Rajendiran N, Swaminathan M (1996) Indian J Chem 35A:818
41. Hepworth DJ, Mason D, Hallas G, Marsden R (1985) Dyes Pigm 6:389
42. Krishnamoorthy G, Dogra SKJ (1999) Photochem Photobiol A Chem 123:109
43. Kim TH, Cho DW, Yoon M, Kim D (1996) J Phys Chem 160:15670
44. Jiang YB (1995) J Photochem Photobiol A Chem 88:109
45. Agbaria RA, Uzar B, Gill D (1989) J Phys Chem 93:3855
46. Stalin T, Rajendiran N (2006) Chem Phys 322:311
47. Stalin T, Rajendiran N (2006) J Photochem Photobiol A Chem 182:137
48. Stalin T, Rajendiran N (2006) J Photochem Photobiol A Chem 177:144
49. Balasubramanian T, Rajendiran N (2008) Spectrochim Acta 69A:822
50. Antony Muthu Prabhu A, Rajendiran N (2010) Indian J Chem 49A:407
51. Benesi HA, Hildebrand JH (1949) J Am Chem Soc 71:2703
52. Antony Muthu Prabhu A, Siva S, Sankaranarayanan RK, Rajendiran N (2010) J Fluoresc 20:43
53. Kano K, Tawiya Y, Hashimoto S (1992) J Incl Phenom 3:287
54. Tabushi I (1984) Tetrahedron 40:269
55. Guo Q-X, Luo S-H, Liu Y-C (1998) J Incl Phenom Mol Recognit Chem 30:173
56. Li S, Purdy WC (1992) Chem Rev 92:1457
57. Matsui Y, Mochida K (1979) Bull Chem Soc Jpn 52:2808
58. Connors KA, Lin SF, Wong AB (1982) J Pharm Sci 71:217
59. Davies DM, Savage JR (1993) J Chem Res (M):0663
60. Davies DM, Deary ME (1995) J Chem Soc Perkin Trans 2:1287
61. Kitagawa M, Hoshi H, Sakurai M, Inoue Y, Chujo R (1987) Carbohydr Res 163:c1
62. Sakurai M, Kitagawa M, Inoue Y, Chujo R (1990) Carbohydr Res 198:181
63. Delaage M (1991) In: Delaage M (ed) Molecular recognition mechanisms, Ch. 1. VCH Publishers, New York
64. Nemethy G (1967) Angew Chem Int Ed Engl 6:195
65. Sueishi Y, Kasahara M, Inoue M, Matsueda K (2003) J Incl Phenom Macrocycl Chem 4:71
66. Liu Y, Zhao YL, Chen Y, Guo DS (2005) Org Biomol Chem 3:584