Photophysics of 2-(4′-N,N-Dimethylaminophenyl)imidazo[4,5-b]pyridine in Micelles: Selective dual fluorescence in sodium dodecylsulphate and Triton X-100

Journal of Fluorescence

Volumn 20, Issue 1, 2010, Pages 135-142

  Dash, Nihar ^a   Krishnamoorthy, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Fluorescent probe; Hydrogen bonding; Prototropic equilibrium; TICT

Indexed keywords

CETYLTRIMETHYLAMMONIUM BROMIDE; DFT CALCULATION; DUAL FLUORESCENCE; FLUORESCENT PROBES; HYDROGEN BONDINGS; MONOCATIONS; NONIONIC; PHOTOPHYSICAL BEHAVIOR; PHOTOPHYSICS; PYRIDINE RINGS; SODIUM DODECYL SULFATE; SODIUM DODECYL SULPHATE; STEADY STATE; TIME-RESOLVED FLUORESCENCE; TRITON X-100;

AMMONIUM COMPOUNDS; DIFFUSERS (OPTICAL); DYES; FLUORESCENCE; HYDROGEN; MICELLES; NITROGEN; PROBES; PROTONATION; PYRIDINE; SULFUR COMPOUNDS;

HYDROGEN BONDS;

2 (4' N,N DIMETHYLAMINOPHENYL)IMIDAZO(4,5 B)PYRIDINE; 2-(4'-N,N-DIMETHYLAMINOPHENYL)IMIDAZO(4,5-B)PYRIDINE; CETRIMIDE; DODECYL SULFATE SODIUM; FLUORESCENT DYE; IMIDAZOLE DERIVATIVE; OCTOXINOL; PYRIDINE DERIVATIVE;

ABSORPTION; ARTICLE; BINDING SITE; CHEMISTRY; ELECTRON TRANSPORT; MICELLE; PH; SPECTROFLUOROMETRY; TIME;

ABSORPTION; BINDING SITES; CETRIMONIUM COMPOUNDS; ELECTRON TRANSPORT; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; IMIDAZOLES; MICELLES; OCTOXYNOL; PYRIDINES; SODIUM DODECYL SULFATE; SPECTROMETRY, FLUORESCENCE; TIME FACTORS;

EID: 77951023564     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-009-0531-6     Document Type: Article

References (37)

1. W Rettig 1986 Charge separation in excited-states of decoupled systems-TICT compounds and implications regarding the development of new lasers-dyes and the primary processes of vision and photosynthesis Angew Chem Int Ed Engl 25 971 988 10.1002/anie.198609711
2. ZR Grabowski K Rotkiewicz W Rettig 2003 Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures Chem Rev 103 10 3899 4031 10.1021/cr940745l 14531716
3. K Bhattacharyya M Chowdhury 1993 Environmental and magnetic field effects on exciplex and twisted charge transfer emission Chem Rev 93 1 507 535 10.1021/cr00017a022 1:CAS:528:DyaK3sXotVahtg%3D%3D
4. Rettig W, Lapouyade R (1994) Fluorescence probes based on twisted intramolecular charge transfer states and other adiabatic photoreactions. In: Lakowicz JR (ed) Topics in fluorescence spectroscopy, probe design and chemical sensing, vol 4. Plenum Press, New York, pp 109-149
5. N Dash FAS Chipem R Swaminathan G Krishnamoorthy 2008 Hydrogen bond induced twisted intramolecular charge transfer in 2-(4′-N, N-dimethylamino) phenylimidazo[4, 5-b]pyridine Chem Phys Lett 460 119 124 10.1016/j.cplett.2008.05.092 1:CAS:528:DC%2BD1cXovVCmt74%3D
6. Fendler JH (1982) Membrane mimetic chemistry. Wiley-Interscience, New York
7. Ramamurthy V (1991) Photochemistry in organized and constrained media. VCH, New York
8. F Lopez F Cuomo A Ceglie L Ambrosone G Palazzo 2008 Quenching and dequenching of pyrene fluorescence by Nucleotide Monophosphates in cationic micelles J Phys Chem B 112 24 7338 7344 10.1021/jp8003344 1:CAS:528: DC%2BD1cXmt1ygurk%3D 18503268
9. AK Singh M Darshi 2002 Fluorescence probe properties of intramolecular charge transfer diphenylbutadienes in micelles and vesicles Biochim Biophys Acta 1563 35 44 10.1016/S0005-2736(02)00372-3 1:CAS:528:DC%2BD38XjsVSksrk%3D 12007623 (Pubitemid 34455041)
10. M Almgren F Grieser JK Thomas 1979 Dynamic and static aspects of solubilization of neutral arenes in ionic micellar solutions J Am Chem Soc 101 2 279 291 10.1021/ja00496a001 1:CAS:528:DyaE1MXhsVantrg%3D
11. G Saroja B Ramachandan S Saha A Samanta 1999 The fluorescence response of a structurally modified 4-aminophthalimide derivative covalently attached to a fatty acid in homogeneous and micellar environments J Phys Chem B 103 15 2906 2911 10.1021/jp983676d 1:CAS:528:DyaK1MXitVagu70%3D
12. A Mohr P Talbiersky HG Korth R Sustmann R Boese D Bläser H Rehage 2007 A new pyrene-based fluorescent probe for the determination of critical micelle concentrations J Phys Chem B 111 45 12985 12992 10.1021/jp0731497 1:CAS:528:DC%2BD2sXht1WmtLnE 17958349 (Pubitemid 350199433)
13. Dash N, Chipem FAS, Krishnamoorthy G Unpublished results
14. P Banerjee S Pramanik A Sarkar SC Bhattacharya 2008 Modulated photophysics of 3-pyrazolyl-2-pyrazoline derivative entrapped in micellar assembly J Phys Chem B 112 24 7211 7219 10.1021/jp800200v 1:CAS:528: DC%2BD1cXmt1yns7Y%3D 18503274
15. A Chakrabarty P Das A Mallick N Chattopadhyay 2008 Effect of surfactant chain length on the binding interaction of a biological photosensitizer with cationic micelles J Phys Chem B 112 12 3684 3692 10.1021/jp709818d 1:CAS:528:DC%2BD1cXisFWktLs%3D 18307338
16. Kosower EM (1968) An introduction to physical organic chemistry. Wiley, New York
17. S Kundu S Maity SC Bera N Chattopadhyay 1997 Twisted intramolecular charge transfer of dimethylaminobenzonitrile in micellar environments-a way to look at the orientation of the probe within the apolar microenvironment J Mol Struct 405 2-3 231 238 10.1016/S0022-2860(96)09596-8 1:CAS:528: DyaK2sXislylsLs%3D (Pubitemid 27195344)
18. SS Jaffer M Sowmiya SK Saha P Purkayastha 2008 Defining the different phases of premicellar aggregation using the photophysical changes of a surface-probing compound J Colloid Interface Sci 325 1 236 242 10.1016/j.jcis.2008.05.013 1:CAS:528:DC%2BD1cXovFOqtrk%3D 18538335
19. G Krishnamoorthy SK Dogra 2000 Twisted intramolecular charge transfer of 2-(4′-N, N-dimethylaminophenyl)pyrido[3, 4-d]imidazole in cyclodextrins: Effect of pH J Phys Chem A 104 12 2542 2551 10.1021/jp992792t 1:CAS:528:DC%2BD3cXht1GqurY%3D
20. M Shannigrahi S Bagchi 2004 Use of fluorescence probes for characterization of solvation properties of micelles: a linear solvation energy relationship study J Phys Chem B 108 46 17703 17708 10.1021/jp048696w 1:CAS:528:DC%2BD2cXosVSmu7g%3D
21. N Deb M Shannigrahi S Bagchi 2008 Use of fluorescence probes for studying kamlet-taft solvatochromic parameters of micellar system formed by binary mixture of sodium dodecyl sulfate and Triton-X 100 J Phys Chem B 112 10 2868 2873 10.1021/jp710299t 1:CAS:528:DC%2BD1cXitVantr0%3D 18278903
22. G Krishnamoorthy SK Dogra 1999 Twisted intramolecular charge transfer emission of 2-(4′-N, N-dimethylaminophenyl)benzimidazole in micelles J Colloid Interface Sci 213 1 53 61 10.1006/jcis.1999.6091 1:CAS:528: DyaK1MXitFOnsb8%3D 10191006 (Pubitemid 29394401)
23. M Gaber SA El-Daly YS El-Sayed 2008 Spectral properties and inclusion of 3-(4′-dimethylaminophenyl)-1-(2-furanyl)prop-2-en-1-one in organized media of micellar solutions, beta-cyclodextrin and viscous medium Colloid Surf B 66 1 103 109 10.1016/j.colsurfb.2008.05.015 1:CAS:528:DC%2BD1cXoslOgs7s%3D
24. YH Kim DW Cho M Yoon D Kim 1996 Observation of hydrogen-bonding effects on twisted intramolecular charge transfer of p-(N, N-diethylamino)benzoic acid in aqueous cyclodextrin solutions J Phys Chem 100 39 15670 15676 10.1021/jp9613652 1:CAS:528:DyaK28XlsVWitbg%3D (Pubitemid 126838007)
25. G Krishnamoorthy SK Dogra 2000 Effect of micelles on the prototropic equilibrium of 2-(4′-N, N-dimethylaminophenyl)pyrido[3, 4-d]imidazole Phys Chem Chem Phys 2 11 2521 2528 10.1039/b001284j
26. G Krishnamoorthy SK Dogra 1999 Spectral characteristics of the various prototropic species of 2-(4′-N, N-dimethylaminophenyl)pyrido[3, 4-d]imidazole J Org Chem 64 18 6566 6574 10.1021/jo9822986 1:CAS:528: DyaK1MXkvF2ru7g%3D 11674658 (Pubitemid 29426989)
27. W Kohn LJ Sham 1965 Self-consistent equations including exchange and correlation effects Phys Rev A 140 1133 1138 10.1103/PhysRev.140.A1133
28. AD Becke 1993 Density-functional thermochemistry.3. the role of exact exchange J Chem Phys 98 7 5648 5652 10.1063/1.464913 1:CAS:528: DyaK3sXisVWgtrw%3D
29. CT Lee W Yang RG Parr 1988 Development of the Colle-Savetti correlation-energy formula into a functional of the electron-density Phys Rev B 37 2 785 789 10.1103/PhysRevB.37.785 1:CAS:528:DyaL1cXktFWrtbw%3D
30. Casida ME (1995) In: Chong DP (ed) Recent Advances in Density Functional Methods, Part I. World Scientific, Singapore, p 155
31. E Gross J Dobson M Petersilka 1996 Top Curr Chem 181 81 172 10.1007/BFb0016643 1:CAS:528:DyaK2sXjslGrtA%3D%3D
32. A Dreuw JL Weisman MJ Head-Gordon 2003 Chem Phys 119 2943 2946 1:CAS:528:DC%2BD3sXlvVWltbg%3D
33. AL Sobolewski W Domcke 2003 Chem Phys 294 73 83 10.1016/S0301-0104(03) 00388-4 1:CAS:528:DC%2BD3sXnsVahsrY%3D
34. SK Das SK Dogra 1998 Excited state intramolecular proton transfer of 2-(2′-hydroxyphenyl)benzimidazole in non-ionic micelles: Brijs J Chem Soc Faraday Trans I 94 1 139 145 10.1039/a703656f 1:CAS:528:DyaK1cXhtVegtA%3D%3D (Pubitemid 128758311)
35. S Pandey RS Sarpal SK Dogra 1995 Luminescence characteristics of 5-aminoindazole in cationic and anionic micelles at various pH J Colloid Interface Sci 172 2 407 414 10.1006/jcis.1995.1271 1:CAS:528:DyaK2MXlvFSrtbk%3D
36. CJ Drummond F Grieser TW Healy 1989 Acid-base equilibria in aqueous micellar solutions. 1. Simple weak acids and bases J Chem Soc Faraday Trans 1 85 3 521 535 10.1039/f19898500521 1:CAS:528:DyaL1MXhsVagu7s%3D
37. LS Romsted D Zanethe 1988 Quantitative treatment of indicator equilibria in micellar solutions of sodium decyl phosphate and sodium lauryl sulfate J Phys Chem 92 16 4690 4698 10.1021/j100327a027 1:CAS:528:DyaL1cXkvVShtb8%3D