Excited state lactim to lactam type tautomerization reaction in 5-(4-fluorophenyl)-2-hydroxypyridine: Spectroscopic study and quantum chemical calculation

Journal of Fluorescence

Volumn 21, Issue 1, 2011, Pages 95-104

  Samanta, Anuva ^a   Paul, Bijan Kumar ^a   Kar, Samiran ^a   Guchhait, Nikhil ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

5 (4 fluorophenyl) 2 hydroxypyridine; Density Functional Theory (DFT); Fluorescence; Tautomerization; Time Dependent Density Functional Theory (TDDFT)

Indexed keywords

2-HYDROXYPYRIDINE; BARRIER ENERGY; DIFFERENT SOLVENTS; FREE ENERGY CHANGE; HARTREE-FOCK; ISOMERISATION; LOCAL EMISSIONS; PHOTOPHYSICAL PROPERTIES; POLARIZED CONTINUUM MODELS; PROTIC SOLVENTS; QUANTUM CHEMICAL CALCULATIONS; RED-SHIFTED EMISSION; SPECTROSCOPIC STUDIES; STEADY STATE; STRUCTURAL CALCULATIONS; TAUTOMERIC EQUILIBRIA; TAUTOMERIZATIONS; TIME DEPENDENT DENSITY FUNCTIONAL THEORY (TDDFT); TIME-RESOLVED SPECTROSCOPY;

CONTINUUM MECHANICS; EQUILIBRIUM CONSTANTS; EXCITED STATES; FLUORESCENCE; ISOMERS; QUANTUM CHEMISTRY; QUANTUM THEORY; SPECTROSCOPIC ANALYSIS;

DENSITY FUNCTIONAL THEORY;

EID: 79951514525     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-010-0692-3     Document Type: Article

References (37)

1. F Parsapour DF Kelley 1996 Torsional and proton transfer dynamics in substituted 3-hydroxyflavones J Phys Chem 100 2791 2798 1:CAS:528: DyaK28XotlWnsw%3D%3D 10.1021/jp9520106 (Pubitemid 126789081)
2. A Sytnik M Kasha 1994 Excited-state intramolecular proton transfer as a fluorescence probe for protein binding-site static polarity Proc Natl Acad Sci USA 91 8627 8630 1:CAS:528:DyaK2cXmvFKgtrg%3D 10.1073/pnas.91.18.8627 8078934 (Pubitemid 24273717)
3. S Kim SY Park 2003 Photochemically gated protonation effected by intramolecular hydrogen bonding: towards stable fluorescence imaging in polymer films Adv Mater 15 1341 1344 1:CAS:528:DC%2BD3sXntFyjur4%3D 10.1002/adma. 200305050
4. J Catalán JC del Valle RM Claramunt D Sanz J Dotor 1996 Photophysics of the 2-(2′-hydroxyphenyl)perimidine: on the fluorescence of the enol form J Lumin 68 165 170 10.1016/0022-2313(96)00005-1 (Pubitemid 126359458)
5. PT Chou D McMorrow TJ Aartsma M Kasha 1984 The proton-transfer laser. Gain spectrum and amplification of spontaneous emission of 3-hydroxyflavone J Phys Chem 88 4596 4599 1:CAS:528:DyaL2cXlsVSlu78%3D 10.1021/j150664a032
6. AV Acuna F Amat-Guerri J Catalán A Costella J Figuera J Munoz 1986 Pulsed liquid lasers from proton transfer in the excited state Chem Phys Lett 132 567 569 1:CAS:528:DyaL2sXptlWrsg%3D%3D 10.1016/0009-2614(86)87126-3
7. KI Sakai T Tsuzuki Y Itoh M Ichikawa Y Taniguchi 2003 Using proton-transfer laser dyes for organic laser diodes Appl Phys Lett 86 081103 10.1063/1.1868885
8. AD Roshal AV Grigorovich AO Doroshenko VG Pivovarenko 1998 Flavonols and crown-flavonols as metal cation chelators. The different nature of Ba2+ and Mg2+ complexes J Phys Chem A 102 5907 5914 1:CAS:528:DyaK1cXktVygsbY%3D 10.1021/jp972519w (Pubitemid 128604894)
9. CL Renschler LA Harrah 1985 Reduction of reabsorption effects in scintillators by employing solutes with large stokes shifts Nucl Instrum Methods Phys Res Sect A 235 41 45 10.1016/0168-9002(85)90243-8
10. S Kim J Seo HK Jung JJ Kim SY Park 2005 White luminescence from polymer thin films containing excited-state intramolecular proton-transfer dyes Adv Mater 17 2077 2082 1:CAS:528:DC%2BD2MXhtVaksbbK 10.1002/adma.200401739 (Pubitemid 41288225)
11. A Weisstuch P Neidig AC Testa 1975 Fluorescence study of hydroxypyridines J Lumin 10 137 144 1:CAS:528:DyaE2MXlsVKlurs%3D 10.1016/0022-2313(75)90042-3
12. OK Abou-Zied OIK Al-Shihi 2008 Characterization of subdomain IIA binding site of human serum albumin in its native, unfolded, and refolded states using small molecular probes J Am Chem Soc 130 10793 10801 1:CAS:528: DC%2BD1cXos12qs7g%3D 10.1021/ja8031289 18642807
13. MR Nimlos DF Kelly ER Bernstein 1989 Spectroscopy, structure, and proton dynamics of 2-hydroxypyridine and its clusters with water and ammonia J Phys Chem 93 643 651 1:CAS:528:DyaL1MXls12kuw%3D%3D 10.1021/j100339a030
14. A Held DW Pratt 1993 Ammonia as a hydrogen bond donor and acceptor in the gas phase. Structures of 2-Pyridone-NH3 and 2-Pyridone-(NH& in Their SO and S1 Electronic States J Am Chem Soc 115 9718 9723 1:CAS:528:DyaK2cXotFai 10.1021/ja00074a043
15. Y Matsuda T Ebata N Mikami 2001 IR-UV double-resonance spectroscopic study of 2-Hydroxypyridine and its hydrogen-bonded clusters in supersonic jets J Phys Chem A 105 3475 3480 1:CAS:528:DC%2BD3MXhslCksr4%3D 10.1021/jp003272x (Pubitemid 35377887)
16. JD Watson FHC Crick 1953 Genetical implications of the structure of deoxyribonucleic acid Nature 171 964 967 1:CAS:528:DyaG3sXlsFWgtQ%3D%3D 10.1038/171964b0 13063483
17. MD Topal JR Fresco 1976 Complementary base pairing and the origin of substitution mutations Nature 263 285 289 1:CAS:528:DyaE2sXltFOisw%3D%3D 10.1038/263285a0 958482
18. Mehler HR, Cordes EH (1971) Biological chemistry, 2nd edn. Harper and Row, New York
19. B Pullman A Oullman 1971 Electronic aspects of purine tautomerism Adv Heterocycl Chem 13 77 159 10.1016/S0065-2725(08)60349-9
20. MJ Scanlan IH Hillier 1984 On the mechanism of proton transfer in the 2-hydroxypyridine α 2-pyridone tautomeric equilibrium Chem Phys Lett 107 330 332 1:CAS:528:DyaL2cXltFShtLo%3D 10.1016/0009-2614(84)85138-6
21. M Moreno WH Miller 1990 On the tautomerization reaction 2-pyridone 2-hydroxypyridine: an ab initio study Chem Phys Lett 171 475 479 1:CAS:528:DyaK3cXlvFSmsr0%3D 10.1016/0009-2614(90)85249-C
22. AL Sobolewski 1993 The mechanism of excited-state hydrogen transfer in 2-hydroxypyridine Chem Phys Lett 211 293 299 1:CAS:528:DyaK3sXmt1Gms78%3D 10.1016/0009-2614(93)87062-8
23. V Barone C Adamo 1994 A theoretical investigation of potential energy surfaces governing the photochemical tautomerization of 2-pyridone Chem Phys Lett 226 399 404 1:CAS:528:DyaK2cXmvV2gtb8%3D 10.1016/0009-2614(94)00744-6
24. MJ Nowak L Lapinski J Fulara A Les L Adamowicz 1992 Matrix isolation IR spectroscopy of tautomeric systems and its theoretical interpretation. 2-Hydroxypyridine/2(1 H)-Pyridinone J Phys Chem 96 1562 1569 1:CAS:528:DyaK38XhtVGntbk%3D 10.1021/j100183a015
25. Kuzuya M, Noguchi A, Okuda T (1984) Fluorescence spectroscopic detection of the pyridinol form in tautomeric 2(1H)-pyridones. J Chem Soc Chem Commun 435-436
26. AL Sobolewski L Adamowicz 1996 Photophysics of 2-Hydroxypyridine: an ab initio study J Phys Chem 100 3933 3941 1:CAS:528:DyaK28XhtVKktr8%3D 10.1021/jp950852z (Pubitemid 126793322)
27. R Church R Trust JD Albright D Powell 1995 New synthetic routes to 3-, 5-, and 6-Aryl-2-chloropyridines J Org Chem 60 3750 3758 1:CAS:528: DyaK2MXlvFWruro%3D 10.1021/jo00117a029
28. A Mahata D Sarkar D Bose D Ghosh A Girigoswami P Das N Chattopadhyay 2009 Photophysics and rotational dynamics of a β-Carboline analogue in nonionic micelles: effect of variation of length of the headgroup and the tail of the surfactant J Phys Chem B 113 7517 7526 1:CAS:528:DC%2BD1MXltl2ht7w%3D 10.1021/jp900575e 19413359
29. Frisch MJ et al (2003) Gaussian 03, Revision B.03, Gaussian, Inc. Pittsburgh, PA
30. S Mahanta RB Singh S Kar N Guchhait 2006 Excited state intramolecular proton transfer in 3-hydroxy-2-naphthaldehyde: a combined study by absorption and emission spectroscopy and quantum chemical calculation Chem Phys 324 742 752 1:CAS:528:DC%2BD28XkvFKqu78%3D 10.1016/j.chemphys.2006.01.036
31. RB Singh S Mahanta S Kar N Guchhait 2007 Photo-physical properties of 1-hydroxy-2-naphthaldehyde: a combined fluorescence spectroscopy and quantum chemical calculations Chem Phys 331 373 384 1:CAS:528:DC%2BD28XhtlCrurvM 10.1016/j.chemphys.2006.11.007
32. AAM Prabhu S Siva RK Sankaranarayanan N Rajendiran 2010 Intramolecular proton transfer effects on 2, 6-diaminopyridine J Fluoresc 20 43 54 1:CAS:528:DC%2BC3cXhslegs7g%3D 10.1007/s10895-009-0520-9 19669393
33. n (n = 0 - 2) in the ground and excited states J Phys Chem A 109 3983 3990 1:CAS:528:DC%2BD2MXjtFSju7c%3D 10.1021/jp044498t 16833720 (Pubitemid 40680413)
34. BK Paul S Mahanta RB Singh N Guchhait 2010 A DFT-based theoretical study on the photophysics of 4-hydroxyacridine: single-water-mediated excited state proton transfer J Phys Chem A 114 2618 2627 1:CAS:528:DC%2BC3cXhtlWlt7k%3D 10.1021/jp909029c 20121061
35. SJ Formosinho LG Arnaut 1993 Excited-state proton transfer reactions II. Intramolecular reactions J Photochem Photobiol A Chem 75 21 48 1:CAS:528:DyaK2cXnvV2j 10.1016/1010-6030(93)80158-6
36. K Justin Y Wu J Bredas VS Batista 2009 Quantum dynamics of the excited-state intramolecular proton transfer in 2-(2′-Hydroxyphenyl) benzothiazole Isr J Chem 49 187 197 10.1560/IJC.49.2.187
37. C Schriever M Barbatti K Stock AJA Aquino D Tunega S Lochbrunner E Riedle R de Vivie-Riedle H Lischka 2008 The interplay of skeletal deformations and ultrafast excited-state intramolecular proton transfer: experimental and theoretical investigation of 10-hydroxybenzo[h]quinoline Chem Phys 347 446 461 1:CAS:528:DC%2BD1cXlslKmt7s%3D 10.1016/j.chemphys.2007.10.021