Fluorescent coumarin derivatives with large stokes shift, dual emission and solid state luminescent properties: An experimental and theoretical study

Dyes and Pigments

Volumn 92, Issue 3, 2012, Pages 1361-1369

  Xie, Lijuan ^a,b   Chen, Yinghui ^a,b   Wu, Wenting ^b   Guo, Huimin ^b   Zhao, Jianzhang ^b   Yu, Xuerong ^b  

^a HUAQIAO UNIVERSITY   (China)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Coumarin; Density functional theory; ESIPT; Fluorescence; Photochemistry; Photophysics

Indexed keywords

COUMARIN; COUMARIN DERIVATIVES; DENSITY FUNCTIONALS; DUAL EMISSIONS; ESIPT; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; FRONTIER MOLECULAR ORBITALS; LUMINESCENT PROPERTY; PHOTOPHYSICS; POTENTIAL ENERGY CURVES; RE-DISTRIBUTION; ROTAMERS; STOKES SHIFT; THEORETICAL STUDY;

CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; FLUORESCENCE; MOLECULAR ORBITALS; POTENTIAL ENERGY;

EXCITED STATES;

EID: 80054713276     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.09.023     Document Type: Article

References (39)

1. W.Y. Lin, L.L. Long, and W. Tan A highly sensitive fluorescent probe for detection of benzenethiols in environmental samples and living cells Chem Commun 46 2010 1503 1505
2. S. Park, J.E. Kwon, S.H. Kim, J. Seo, K. Chung, and S.Y. Park A white-light-emitting molecule: frustrated energy transfer between constituent emitting centers J Am Chem Soc 131 2009 14043 14049
3. W.Y. Lin, L.L. Long, J.B. Feng, B. Wang, and C.C. Guo Synthesis of meso-coumarin-conjugated porphyrins and investigation of their luminescence properties Eur J Org Chem 2007 4301 4304
4. H.Q. Li, L. Cai, J.X. Li, Y.X. Hu, P.P. Zhou, and J.M. Zhang Novel coumarin fluorescent dyes: synthesis, structural characterization and recognition behavior towards Cu (II) and Ni (II) Dyes Pigments 91 2011 309 316
5. K.D. Seo, H.M. Song, M.J. Lee, M. Pastore, C. Anselmi, and A.F. De Coumarin dyes containing low-band-gap chromophores for dye-sensitised solar cells Dyes Pigments 90 2011 304 310
6. Z.W. Xu, G.H. Ding, G.Y. Zhong, G.C. Xing, F.Y. Li, and W. Huang Color tunable organic light-emitting diodes using coumarin dopants Res Chem Intermed 34 2008 249 256 (Pubitemid 351270030)
7. N.C. Lim, J.V. Schuster, M.C. Porto, M.A. Tanudra, L.L. Yao, and H.C. Freake Coumarin-based chemosensors for zinc (II): toward the determination of the design algorithm for CHEF-type and ratiometric probes Inorg Chem 44 2005 2018 2030 (Pubitemid 40431492)
8. M.S. Schiedel, C.A. Briehn, and P. Bäuerle Single-compound libraries of organic materials: parallel synthesis and screening of fluorescent dyes Angew Chem Int Ed 40 2001 4677 4680 (Pubitemid 34032205)
9. A.R. Jagtap, V.S. Satam, R.N. Rajule, and V.R. Kanetkar The synthesis and characterization of novel coumarin dyes derived from 1,4-diethyl-1,2,3,4- tetrahydro-7-hydroxyquinoxalin-6-carboxaldehyde Dyes Pigments 82 2009 84 89
10. S.H. Zhou, J.H. Jia, J.R. Gao, L. Han, Y.J. Li, and W.J. Sheng The one-pot synthesis and fluorimetric study of 3-(2′-benzothiazolyl) coumarins Dyes Pigments 86 2010 123 128
11. J.R. Lakowicz Principles of fluorescence spectroscopy 2nd ed 1999 Kluwer Academic/Plenum Publishers New York p. 75
12. 2-chelated fluorophores based on 2-(2′-hydroxyphenyl) benzoxazole and 2-(2′-hydroxyphenyl) benzothiazole Bull Kor Chem Soc 30 2009 2865 2866
13. R.V. Sonia, M. Crr, M. Manuel, and R.P. Flor Excited-state intramolecular proton transfer in 2-(3′-Hydroxy-2′-pyridyl)benzoxazole. Evidence of coupled proton and charge transfer in the excited state of some o-hydroxyarylbenzazoles J Phys Chem A 111 2007 1814 1826
14. I. Toshiyuki, M. Atsuya, S. Yoshihiro, S. Tomoo, N. Yoshinobu, and A. Tatsuo Excited-state intramolecular proton transfer of naphthalene-fused 2-(2′-hydroxyaryl)benzazole family J Phys Chem A 114 2010 1603 1609
15. K. Ajaykumar, A.P. Sangamesh, and S.B. Prema Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La(III), Th(IV) and VO(IV) complexes with Schiff bases of coumarin derivatives Eur J Med Chem 44 2009 2904 2912
16. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 09, revision D.01 2009 Gaussian Inc. Wallingford, CT
17. W.H. Sun, S.Y. Li, R. Hu, Y. Qian, S.Q. Wang, and G.Q. Yang Understanding solvent effects on luminescent properties of a triple fluorescent ESIPT compound and application for white light emission J Phys Chem A 113 2009 5888 5895
18. G. Signore, R. Nifosi, L. Albertazzi, B. Storti, and R. Bizzarri Polarity-sensitive coumarins tailored to live cell imaging J Am Chem Soc 132 2010 1276 1288
19. S.T. Huang, J.L. Jian, H.Z. Peng, K.L. Wang, C.M. Lin, and C.H. Huang The synthesis and optical characterization of novel iminocoumarin derivatives Dyes Pigments 86 2010 6 14
20. F. Han, L.N. Chi, W.T. Wu, X.F. Liang, M.Y. Fu, and J.Z. Zhao J Photoch Photobiol A 196 2008 10 23
21. S.Y. Park, M. Ebihara, Y. Kubota, K. Funabiki, and M. Matsui Dyes Pigments 82 2009 258 267
22. T. Kowalczyk, Z.L. Lin, and T.V. Voorhis J Phys Chem A 114 2010 10427 10434
23. G.J. Zhao, J.Y. Liu, L.C. Zhou, and K.L. Han Site-selective photoinduced electron transfer from alcoholic solvents to the chromophore facilitated by hydrogen bonding: a new fluorescence quenching mechanism J Phys Chem B 111 2007 8940 8945
24. F. Han, L. Chi, X. Liang, S. Ji, S. Liu, and F. Zhou 3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid J Org Chem 74 2009 1333 1336
25. S. Ji, J. Yang, Q. Yang, S. Liu, M. Chen, and J. Zhao Tuning the intramolecular charge transfer of alkynylpyrenes: effect on photophysical properties and its application in design of OFF-ON fluorescent thiol probes J Org Chem 74 2009 4855 4865
26. X. Zhang, L.N. Chi, S.M. Ji, Y.B. Wu, P. Song, and K.L. Han Rational design of d-PeT phenylethynylated-carbazole monoboronic acid fluorescent sensors for the selective detection of α-hydroxyl carboxylic acids and monosaccharides J Am Chem Soc 131 2009 17452 17463
27. J. Shao, H. Guo, S. Ji, and J. Zhao Styryl-BODIPY based red-emitting fluorescent OFF-ON molecular probe for specific detection of cysteine Biosens Bioelectron 26 2011 3012 3017
28. H. Guo, Y. Jing, X.L. Yuan, S.M. Jia, J.Z. Zhao, and X.H. Li Highly selective fluorescent OFF-ON thiol probes based on dyads of BODIPY and potent intramolecular electron sink 2,4-dinitrobenzenesulfonyl subunits Org Biomol Chem 9 2011 3844 3853
29. S. Ji, W. Wu, W. Wu, P. Song, K. Han, and Z. Wang Tuning the luminescence lifetimes of ruthenium(II) polypyridine complexes and its application in luminescent oxygen sensing J Mater Chem 20 2010 1953 1963
30. W. Wu, W. Wu, S. Ji, H. Guo, X. Wang, and J. Zhao The synthesis of 5,10,15,20-tetraarylporphyrins and their platinum(II) complexes as luminescent oxygen sensing materials Dyes Pigments 89 2011 199 211
31. S. Ji, H. Guo, X. Yuan, X. Li, H. Ding, and P. Gao A highly selective OFF-ON red-emitting phosphorescent thiol probe with large Stokes shift and long luminescent lifetime Org Lett 12 2010 2876 2879
32. W. Wu, W. Wu, S. Ji, H. Guo, and J. Zhao Observation of room-temperature deep-red/near-IR phosphorescence of pyrene with cycloplatinated complexes: an experimental and theoretical study Eur J Inorg Chem 2010 4470 4482
33. W. Wu, C. Cheng, W. Wu, H. Guo, S. Ji, and P. Song Tuning the emission colour of triphenylamine-capped cyclometallated platinum(ii) complexes and their application in luminescent oxygen sensing and organic light-emitting diodes Eur J Inorg Chem 2010 4683 4696
34. W. Wu, W. Wu, S. Ji, H. Guo, P. Song, and K. Han Tuning the emission properties of cyclometalated platinum(II) complexes by intramolecular electron-sink/arylethynylated ligands and its application for enhanced luminescent oxygen sensing J Mater Chem 20 2010 9775 9786
35. H. Sun, H. Guo, W. Wu, X. Liu, and J. Zhao Coumarin phosphorescence observed with N^ N Pt(II) bisacetylide complex and its applications for luminescent oxygen sensing and triplet-triplet-annihilation based upconversion Dalton Trans 40 2011 7834 7841
36. 3il excited states and their application in triplet-triplet-annihilation based upconversion Eur J Inorg Chem 2011 3165 3173
37. T. Iijima, A. Momotake, Y. Shinohara, T. Sato, Y. Nishimura, and T. Arai Excited-state intramolecular proton transfer of naphthalene-fused 2-(2′-hydroxyaryl)benzazole family J Phys Chem A 114 2010 1603 1609
38. M. Ikegami, and T. Arai Photoinduced intramolecular hydrogen atom transfer in 2-(hydroxyphenyl)benzoxazole and 2-(2-hydroxyphenyl)benzothiazole studied by laser flash photolysis J Chem Soc Perkin Trans 2 2002 1296 1301 (Pubitemid 35188115)
39. G.J. Zhao, R.K. Chen, M.T. Sun, J.Y. Liu, G.Y. Li, and Y.L. Gao Photoinduced intramolecular charge transfer and S2 fluorescence in thiophene-π-conjugated donor-acceptor systems: experimental and TDDFT studies Chem Eur J 14 2008 6935 6947