Unsaturated oxazolones as nonlinear fluorophores

Dyes and Pigments

Volumn 99, Issue 3, 2013, Pages 642-652

  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; GFP analogue; Nonlinear; Oxazolone; Push pull; Two photon absorption

Indexed keywords

GFP ANALOGUE; NONLINEAR; OXAZOLONE; PUSH-PULL; TWO-PHOTON ABSORPTIONS;

FLUORESCENCE; FLUOROPHORES;

TWO PHOTON PROCESSES;

EID: 84882481300     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.06.012     Document Type: Article

References (33)

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 (Pubitemid 351638815)
2. A. Diaspro, G. Chirico, and M. Collini Two-photon fluorescence excitation and related techniques in biological microscopy Q Rev Biophys 38 02 2005 97 166 (Pubitemid 43872054)
3. M. Drobizhev, N.S. Makarov, S.E. Tillo, T.E. Hughes, and A. Rebane Two-photon absorption properties of fluorescent proteins Nat Methods 8 5 2011 393 399
4. 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
5. 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
6. 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
7. D. Uraguchi, Y. Ueki, and T. Ooi Chiral tetraaminophosphonium carboxylate-catalyzed direct Mannich-type reaction J Am Chem Soc 130 43 2008 14088 14089
8. 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
9. 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
10. 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
11. L.X. Wu, and K. Burgess Syntheses of highly fluorescent GFP-chromophore analogues J Am Chem Soc 130 12 2008 4089 4096 (Pubitemid 351429879)
12. J.T. Kang, G.Y. Zhao, J.W. Xu, and W. Yang A synthesized GFP analogue emits via a hydrogen-bonding system Chem Commun 46 16 2010 2868 2870
13. 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
14. 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 Dye Pigment 56 2 2003 125 133 (Pubitemid 36073235)
15. 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
16. 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
17. M. Blanco-Lomas, S. Samanta, P.J. Campos, G.A. Woolley, and D. Sampedro Reversible photocontrol of peptide conformation with a rhodopsin-like photoswitch J Am Chem Soc 134 16 2012 6960 6963
18. M. Blanco-Lomas, P.J. Campos, and D. Sampedro Benzylidene-oxazolones as molecular photoswitches Org Lett 14 17 2012 4334 4337
19. C.A.B. Rodrigues, I.F.A. Mariz, E.M.S. Macoas, C.A.M. Afonso, and J.M.G. Martinho Two-photon absorption properties of push-pull oxazolones derivatives Dye Pigment 95 3 2012 713 722
20. 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 (Pubitemid 35283641)
21. 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 (Pubitemid 351434377)
22. 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
23. A.W. Ingersoll, and S.H. Babcock Hippuric acid Org Synth 12 1932 40 42
24. B.M. Lienard, A. Conejo-Garcia, I. Stolze, C. Loenarz, N.J. Oldham, and P.J. Ratcliffe Evaluation of aspirin metabolites as inhibitors of hypoxia-inducible factor hydroxylases Chem Commun 47 2008 6393 6395
25. 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
26. R.M. Acheson, D.A. Booth, R. Brettle, and A.M. Harris The synthesis of some acylglycines and related oxazolones J Chem Soc 1960 Sep 3457 3461
27. 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
28. W.M. Mcclain Excited state symmetry assignment through polarized 2-photon absorption studies of fluids J Chem Phys 55 6 1971 2789 2796
29. P.R. Monson, and W.M. Mcclain Polarization dependence of 2-photon absorption of tumbling molecules with application to liquid 1-chloronaphthalene and benzene J Chem Phys 53 1 1970 29 37
30. Dalton Dalton, a molecular electronic structure program, release Dalton 2011 2011 see: http://daltonprogramorg
31. D. Döpp Reactions of aromatic nitro compounds via excited triplet states Top Curr Chem 55 1975 49 85
32. R. Hurley, and A.C. Testa Triplet-state yield of aromatic nitro compounds J Am Chem Soc 90 8 1968 1949 1952
33. Z.L. Huang, H. Lei, N. Li, Z.R. Qiu, H.Z. Wang, and J.D. Guo Novel heterocycle-based organic molecules with two-photon induced blue fluorescent emission J Mater Chem 13 2003 708 711