Two-photon absorption properties of push-pull oxazolones derivatives

Dyes and Pigments

Volumn 95, Issue 3, 2012, Pages 713-722

  Rodrigues, Catarina A B ^a   Mariz, Inês F A ^b   MaçÔas, Ermelinda M S ^b   Afonso, Carlos A M ^a   Martinho, José M G ^b  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Fluorescence; Nonlinear emission; Oxazolone; Push pull; Solvatochromism; Two photon absorption

Indexed keywords

NONLINEAR EMISSIONS; OXAZOLONE; PUSH-PULL; SOLVATOCHROMISMS; TWO-PHOTON ABSORPTIONS;

CHARGE TRANSFER; COMPLEXATION; FLUORESCENCE; LIGHT ABSORPTION; QUANTUM YIELD; TWO PHOTON PROCESSES;

LUMINESCENCE OF ORGANIC SOLIDS;

EID: 84864482557     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.06.005     Document Type: Article

References (61)

1. G.S. He, L.-S. Tan, Q. Zheng, and P.N. Prasad Multiphoton absorbing materials: molecular designs, characterization, and applications Chem Rev 108 2008 1245 1330
2. M. Pawlicki, H.A. Collins, R.G. Denning, and H.L. Anderson Two-photon absorption and the design of two-photon dyes Angew Chem Int Ed 48 18 2009 3244 3266
3. J.S. Fisk, R.A. Mosey, and J.J. Tepe The diverse chemistry of oxazol-5-(4H)-ones Chem Soc Rev 36 9 2007 1432 1440
4. A.N.R. Alba, and R. Rios Oxazolones in organocatalysis, new tricks for an old reagent Chem Asian J 6 3 2011 720 734
5. R.A. Mosey, J.S. Fisk, and J.J. Tepe Stereoselective syntheses of quaternary substituted alpha-amino acids using oxazol-5-(4H)-ones Tetrahedron-Asymmetry 19 24 2008 2755 2762
6. J. Aleman, A. Milelli, S. Cabrera, E. Reyes, and K.A. Jorgensen Asymmetric 1,4-Addition of oxazolones to Nitroalkenes by Bifunctional cinchona Alkaloid Thiourea organocatalysts: synthesis of alpha, alpha-disubstituted alpha-amino acids Chem Eur J 14 35 2008 10958 10966
7. S. Cabrera, E. Reyes, J. Aleman, A. Milelli, S. Kobbelgaard, and K.A. Jorgensen Organocatalytic asymmetric synthesis of alpha, alpha-disubstituted alpha-amino acids and derivatives J Am Chem Soc 130 36 2008 12031 12037
8. D. Uraguchi, Y. Ueki, and T. Ooi Chiral Tetraaminophosphonium Carboxylate-catalyzed direct Mannich-type reaction J Am Chem Soc 130 43 2008 14088
9. S.X. Dong, X.H. Liu, X.H. Chen, F. Mei, Y.L. Zhang, and B. Gao Chiral Bisguanidine-catalyzed inverse-electron-demand Hetero-Diels-Alder reaction of Chalcones with azlactones J Am Chem Soc 132 31 2010 10650 10651
10. X.D. Liu, L.J. Deng, X.X. Jiang, W.J. Yan, C.L. Liu, and R. Wang Asymmetric Aza-Mannich addition of oxazolones to N-Tosyl Aldimines: synthesis of Chiral alpha-disubstituted alpha, beta-Diamino acids Org Lett 12 4 2010 876 879
11. M. Weber, S. Jautze, W. Frey, and R. Peters Bispalladacycle-catalyzed bronsted acid/base-promoted asymmetric Tandem azlactone formation-Michael addition J Am Chem Soc 132 35 2010 12222 12225
12. X. Yang, G.J. Lu, and V.B. Birman Benzotetramisole-catalyzed dynamic kinetic resolution of azlactones Org Lett 12 4 2010 892 895
13. A.N.R. Alba, T. Calbet, M. Font-Bardia, A. Moyano, and R. Rios Alkylation of oxazolones and related heterocycles through an S(N)1 reaction Eur J Org Chem 11 2011 2053 2056
14. C.K. De, N. Mittal, and D. Seidel A dual-catalysis approach to the asymmetric steglich rearrangement and catalytic enantioselective addition of o-acylated azlactones to isoquinolines J Am Chem Soc 133 42 2011 16802 16805
15. M. Di Giacomo, M. Serra, M. Brusasca, and L. Colombo Stereoselective Pd-catalyzed synthesis of quaternary alpha-D-C-Mannosyl-(S)-amino acids J Org Chem 76 13 2011 5247 5257
16. S.X. Dong, X.H. Liu, Y.L. Zhang, L.L. Lin, and X.M. Feng Asymmetric synthesis of 3, 4-Diaminochroman-2-ones promoted by guanidine and bisguanidium salt Org Lett 13 19 2011 5060 5063
17. G.J. Lu, and V.B. Birman Dynamic kinetic resolution of azlactones catalyzed by Chiral Bronsted acids Org Lett 13 3 2011 356 358
18. A.D. Melhado, G.W. Amarante, Z.J. Wang, M. Luparia, and F.D. Toste Gold(I)-Catalyzed Diastereo- and enantioselective 1,3-Dipolar cycloaddition and Mannich reactions of azlactones J Am Chem Soc 133 10 2011 3517 3527
19. M. Terada, and H. Nii Highly Stereoselective 4+2 cycloaddition of azlactones to beta, gamma-unsaturated alpha-Ketoesters catalyzed by an axially Chiral Guanidine base Chem Eur J 17 6 2011 1760 1763
20. M.D. Truppo, and G. Hughes Development of an improved immobilized CAL-B for the Enzymatic resolution of a key intermediate to Odanacatib Org Proc Res Dev 15 5 2011 1033 1035
21. Y. Ying, Z. Chai, H.F. Wang, P. Li, C.W. Zheng, and G. Zhao Bifunctional cinchona alkaloids-catalyzed asymmetric 4+2 cycloaddition reaction of beta, gamma-unsaturated alpha-keto esters with oxazolones Tetrahedron 67 19 2011 3337 3342
22. K. Ertekin, S. Alp, C. Karapire, B. Yenigül, E. Henden, and S. İçli Fluorescence emission studies of an azlactone derivative embedded in polymer films: an optical sensor for pH measurements J Photochem Photobiol A: Chem 137 2-3 2000 155 161
23. K. Ertekin, S. Alp, and I. Yalcin Determination of pK(a) values of azlactone dyes in non-aqueous media Dyes Pigment 65 1 2005 33 38
24. K. Ertekin, C. Karapire, S. Alp, B. Yenigül, and S. Içli Photophysical and photochemical characteristics of an azlactone dye in sol-gel matrix; a new fluorescent pH indicator Dyes Pigment 56 2 2003 125 133
25. L.X. Wu, and K. Burgess Syntheses of highly fluorescent GFP-chromophore analogues J Am Chem Soc 130 12 2008 4089 4096
26. N.C. Misra, and H. Ila 4-Bis(methylthio)methylene-2-phenyloxazol-5-one: versatile template for synthesis of 2-Phenyl-4,5-functionalized Oxazoles J Org Chem 75 15 2010 5195 5202
27. V. Amareshwar, N.C. Mishra, and H. Ila 2-Phenyl-4-bis(methylthio) methyleneoxazol-5-one: versatile template for diversity oriented synthesis of heterocycles Org & Biomol Chem. 9 16 2011 5793 5801
28. M.G.J. Baud, T. Leiser, F.J. Meyer-Almes, and M.J. Fuchter New synthetic strategies towards psammaplin A, access to natural product analogues for biological evaluation Org & Biomol Chem. 9 3 2011 659 662
29. A.R. Genady, and H. Nakamura Amphiphilic allylation of arylidene-1,3-oxazol-5(4H)-one using bis-pi-allylpalladium complexes: an approach to synthesis of cyclohexyl and cyclohexenyl alpha-amino acids Org Biomol Chem 9 20 2011 7180 7189
30. H. Jiang, B. Gschwend, L. Albrecht, S.G. Hansen, and K.A. Jorgensen Asymmetric Trienamine catalysis for the construction of structurally rigid cyclic alpha, alpha-disubstituted amino acid derivatives Chem Eur J 17 33 2011 9032 9036
31. H. Kaur, A.M. Heapy, and M.A. Brimble The synthesis of dehydrotryptophan and dehydrotryptophan-containing peptides Org Biomol Chem 9 17 2011 5897 5907
32. B.M. Trost, and P.J. Morris Palladium-catalyzed Diastereo- and enantioselective synthesis of substituted Cyclopentanes through a dynamic kinetic asymmetric formal 3+2 -Cycloaddition of Vinyl Cyclopropanes and Alkylidene azlactones Angew Chem Int Ed 50 27 2011 6167 6170
33. S.L. Wang, J. Ding, B. Jiang, Y. Gao, and S.J. Tu Microwave-assisted solvent-dependent reaction: chemoselective synthesis of Quinoxalin-2(1H)-ones, Benzo d imidazoles and Dipeptides Acs Comb Sci 13 5 2011 572 577
34. B.M. Krasovitskii, I.V. Lysova, and L.S. Afanasiadi Synthesis and spectral-Luminescence properties of 2-aryloxazole-5-ones Khimiya Geterotsiklicheskikh Soedinenii 2 1978 158 160
35. B.M. Krasovitskii, I.V. Lysova, and L.S. Afanasiadi Synthesis and spectral-lumine scence properties of 2- aryl- 4- benzylide ne-5-oxazolones Chem Heterocyc Comp 16 7 1980 701 703
36. B.M. Krasovitskii, I.V. Lysova, L.S. Afanasiadi, M.B. Stryukov, M.I. Knyazhanskii, and Y.M. Vinetskaya Luminescence properties of compounds containing both 2,5-diaryloxazole and 5-oxazole units J Appl Spectrosc 33 3 1980 930 933
37. B.M. Krasovitskii, I.V. Lysova, L.S. Afanasiadi, and Y.N. Surov Luminophores of the azlactone Series with Difluoromethylsulfonyl groups Khimiya Geterotsiklicheskikh Soedinenii 12 1981 1600 1603
38. M. Kitazawa, R. Higuchi, M. Takasashi, T. Wada, and H. Sasabe Novel molecular design for 2nd-Harmonic generation - Azlactone derivatives J Phys Chem 99 40 1995 14784 14792
39. J.L. Diaz, B. Villacampa, F. Lopez-Calahorra, and D. Velasco Experimental and theoretical study of a new class of acceptor group in chromophores for nonlinear optics: 2-substituted 4-methylene-4H-oxazol-5-ones Chem Mat 14 5 2002 2240 2251
40. H.C. Song, H. Wen, and W.M. Li Study on the second-order optical behavior of 4-(substituted-benzylidene)-2-phenyl-4H-oxazol-5-one Spectrochim Acta A-Mol Biomol Spectrosc 60 7 2004 1587 1591
41. V. Smokal, R. Czaplicki, B. Derkowska, O. Krupka, A. Kolendo, and B. Sahraoui Synthesis and study of nonlinear optical properties of oxazolone containing polymers Synth Met 157 18-20 2007 708 712
42. Y.L.N. Murthy, V. Christopher, U.V. Prasad, P.B. Bisht, D.V. Ramanaih, and B.S. Kalanoor Synthesis and study of nonlinear optical properties of 4-substituted benzylidene-2-phenyl oxazol-5-ones by Z-scan technique Synth Met 160 5-6 2010 535 539
43. B. Derkowska, O. Krupka, V. Smokal, and B. Sahraoui Optical properties of oxazalone derivatives with and without DNA-CTMA Opt Mater 33 9 2011 1429 1433
44. Y.F. Sun, and Y.P. Cui The synthesis, structure and spectroscopic properties of novel oxazolone-, pyrazolone- and pyrazoline-containing heterocycle chromophores Dyes Pigment 81 1 2009 27 34
45. J.S. Buck, and W.S. Ide Azlactone of alpha-benzoylamino-beta-(3,4- dimethoxyphenyl)-acrylic acid 2-phenyl-4-(3 ', 4 '-dimethoxybenzal)- oxazolone Org Synth 13 1933 8 9
46. R.M. Acheson, D.A. Booth, R. Brettle, and A.M. Harris The synthesis of some acylglycines and related Oxazolones J Chem Soc SEP 1960 3457 3461
47. K. König Multiphoton microscopy in life sciences J Microsc 200 2 2000 83 104
48. A. Diaspro, G. Chirico, and M. Collini Two-photon fluorescence excitation and related techniques in biological microscopy Quarter Rev Biophys 38 02 2005 97 166
49. Z.L. Huang, N. Li, H. Lei, Z.R. Qiu, H.Z. Wang, and Z.P. Zhong Two-photon induced blue fluorescent emission of heterocycle-based organic molecule Chem Commun 20 2002 2400 2401
50. N.S. Makarov, M. Drobizhev, and A. Rebane Two-photon absorption standards in the 550-1600 nm excitation wavelength range Opt Express 16 6 2008 4029 4047
51. C. Xu, and W.W. Webb Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm J Opt Soc Am B Opt Phys 13 3 1996 481 491
52. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 03 RC 2004 Gaussian, Inc. Wallingford CT
53. D. Magde, R. Wong, and P.G. Seybold Fluorescence quantum yields and their relation to lifetimes of rhodamine 6G and fluorescein in nine solvents: Improved absolute standards for quantum yields Photochem and Photology 75 4 2002 327 334
54. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, and R. Taylor Tables of bond lengths determined by X-ray and neutron-diffraction.1. Bond lengths in organic-compounds J Chem Soc-Perkin Trans 2 12 1987 S1 S19
55. A. Dreuw, and M. Head-Gordon Single-reference ab initio methods for the calculation of excited states of large molecules Chem Rev 105 11 2005 4009 4037
56. E.F. Ullman, and N. Baumann Unsaturated Lactone Photochemistry - Effect of wavelength and Sensitizer structure on selective population of specific excited states J Am Chem Soc 92 20 1970 5892
57. S. Icli, A.O. Doroshenko, S. Alp, N.A. Abmanova, S.I. Egorova, and S.T. Astley Structure and luminescent properties of the 4-arylidene-2-aryl-5- oxazolones(azlactones) in solution and crystalline state Spectrosc Lett 32 4 1999 553 569
58. Z.R. Grabowski, K. Rotkiewicz, and W. Rettig Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures Chem Rev 103 10 2003 3899 4031
59. J.R. Lakowicz Principles of fluorescence spectroscopy 3rd ed. 2006 Springer US Singapore
60. M. Drobizhev, F.Q. Meng, A. Rebane, Y. Stepanenko, E. Nickel, and C.W. Spangler Strong two-photon absorption in new asymmetrically substituted porphyrins: Interference between charge-transfer and intermediate-resonance pathways J Phys Chem B 110 20 2006 9802 9814
61. A. Rebane, M. Drobizhev, N.S. Makarov, E. Beuerman, J.E. Haley, and M.K. Douglas Relation between two-photon absorption and dipolar properties in a series of Fluorenyl-based chromophores with electron donating or electron withdrawing substituents J Phys Chem A 115 17 2011 4255 4262