Prediction of photophysical properties of pyrimidine chromophores using Taguchi method

Dyes and Pigments

Volumn 110, Issue , 2014, Pages 49-55

  Denneval, Charline ^a   Achelle, Sylvain ^b   Baudequin, Christine ^a   Robin Le Guen, Françoise ^b  

^a NORMANDIE UNIVERSITÉ   (France)

^b INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

Design of experiment; Dyes; Intramolecular charge transfer; Photophysical properties; Pyrimidine; Taguchi method

Indexed keywords

AROMATIC COMPOUNDS; CHARGE TRANSFER; DESIGN OF EXPERIMENTS; DYEING; ORGANIC POLYMERS; TAGUCHI METHODS;

ABSORPTION AND EMISSIONS; CONJUGATED LINKERS; ELECTRON-DONATING GROUP; INTRA-MOLECULAR CHARGE TRANSFER; PHOTOPHYSICAL PROPERTIES; PYRIMIDINE; TAGUCHI DESIGN OF EXPERIMENT; TAGUCHI METHODOLOGY;

CHROMOPHORES;

EID: 84905100576     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2014.05.030     Document Type: Article

References (55)

1. R. Gompper, and H.U. Wagner Donor-acceptor-substituted π-electron systems-probes for theories and building blocks for new materials Angew Chem Int Ed Engl 27 1988 1437 1455
2. Kivala M, Diederich F. Acetylene-derived strong organic acceptors for planar and nonplanar push-pull chromophores. Acc Chem Res;42:235-248.
3. J. Kulhánek, F. Bureš, J. Opršal, W. Kuznik, T. Mikysek, and A. Růžička 1,4-Phenylene and 2,5-thienylene π-linkers in charge-transfer chromophores Asian J Org Chem 2 2013 422 431
4. R. Guliyev, A. Coskun, and E.U. Akkaya Design strategies for ratiometric chemosensors: modulation of excitation energy transfer at the energy donor site J Am Chem Soc 131 2009 9007 9013
5. A.M. Costero, M. Parra, S. Gil, R. Gotor, P.M.E. Mancini, and R. Martínez-Máñez et al. Chromo-fluorogenic detection of nerve-agent mimics using triggered cyclization reactions in push-pull dyes Chem Asian J 5 2010 1573 1585
6. C. Hadad, S. Achelle, I. López-Solera, and J.C. García-Martínez Metal cation complexation studies of 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: effect on the optical properties Dyes Pigments 97 2013 230 237
7. M. Nepraš, N. Almonasy, F. Bureš, J. Kulhánek, M. Dvořák, and M. Michl Fluorescence and photophysical properties of D-π-A push-pull systems featuring a 4,5-dicyanoimidazole unit Dyes Pigments 91 2011 466 473
8. C. Denneval, O. Moldovan, C. Baudequin, S. Achelle, P. Baldeck, and N. Plé et al. Synthesis and photophysical properties of push-pull structures incorporating diazines as attracting part with a fluorene core Eur J Org Chem 2013 5591 5606
9. Y. Lin, Y. Li, and X. Zhan Small molecule semiconductors for high-efficiency organic photovoltaics Chem Soc Rev 41 2012 4245 4272
10. A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, and H. Pettersson Dye-sensitized solar cells Chem Rev 110 2010 6595 6663
11. S. Günes, H. Neugebauer, and N.S. Sariciftci Conjugated polymer-based organic solar cells Chem Rev 107 2007 1324 1338 (Pubitemid 46736541)
12. K. Walzer, B. Maennig, M. Pfeiffer, and K. Leo Highly efficient organic devices based on electrically doped transport layers Chem Rev 107 2007 1233 1271 (Pubitemid 46736538)
13. Y. Yang, Y. Zhou, Q.G. He, C. He, C.H. Yang, and F.L. Bai et al. Solution-processable red-emission organic materials containing triphenylamine and benzothiodiazole units: synthesis and applications in organic light-emitting diodes J Phys Chem B 113 2009 7745 7752
14. S. Barlow, and S.R. Marder Nonlinear optical properties of organic materials T.J.J. Müller, U.H.F. Bunz, Functional organic materials 2007 Wiley-VCH Weinheim, Germany 393 437
15. M. Szablewski, P.R. Thomas, A. Thornton, D. Bloor, G.H. Cross, and J.M. Cole et al. Highly dipolar, optically nonlinear adducts of tetracyano-p- quinodimethane: synthesis, physical characterization, and theoretical aspects J Am Chem Soc 119 1997 3144 3154 (Pubitemid 27204529)
16. R.R. Tykwinski, U. Gubler, R.E. Martin, F. Diederich, C. Bosshard, and P. Günter Structure-property relationships in third-order nonlinear optical chromophores J Phys Chem B 102 1998 4451 4465 (Pubitemid 128578308)
17. T. Taniuchi, S. Okada, and H. Nakanishi Widely tunable terahertz-wave generation in an organic crystal and its spectroscopic application J Appl Phys 95 2004 5984 5988
18. T. Taniuchi, S. Ikeda, Y. Mineno, S. Okada, and H. Nakanishi Terahertz properties of a new organic crystal, 4'-dimethylamino-N-methyl-4-stilbazolium p-chlorobenzenesulfonate Jpn J Appl Phys 44 2005 L932 L934
19. A. Schneider, M. Stillhart, and P. Günter High efficiency generation and detection of terahertz pulses using laser pulses at telecommunication wavelengths Opt Express 14 2006 5376 5384 (Pubitemid 43894210)
20. Z. Yang, L. Mutter, M. Stillhart, B. Ruiz, S. Aravazhi, and M. Jazbinsek et al. Large-size bulk and thin-film stilbazolium-salt single crystals for nonlinear optics and THz generation Adv Funct Mater 17 2007 2018 2023 (Pubitemid 47396184)
21. G.S. He, L.S. Tan, Q. Zheng, and P.N. Prasad Multiphoton absorbing materials: molecular designs, characterizations, and applications Chem Rev 108 2008 1245 1330 (Pubitemid 351638815)
22. J.P. Malval, M. Jin, F. Morlet-Savary, H. Chaumeil, A. Defoin, and O. Soppera et al. Enhancement of the two-photon initiating efficiency of a thioxanthone derivative through a chevron-shaped architecture Chem Mater 23 2011 3411 3420
23. K. Kobayashi, and S.S. Kano Multilayered optical storage with nonlinear read write Opt Rev 2 1995 20 23
24. M.S. Paley, J.M. Harris, H. Looser, J.C. Baumert, G.C. Bjorklund, and D. Jundt et al. A solvatochromic method for determining second-order polarizabilities of organic molecules J Org Chem 54 1989 3774 3778
25. S. Achelle, and N. Plé Pyrimidine ring as building block for the synthesis of functionalized Pi-conjugated materials Curr Org Synth 9 2012 163 187
26. S. Achelle, and C. Baudequin Recent advances in pyrimidine derivatives as luminescent, photovoltaic and non-linear optical materials Targets Heterocycl Syst 17 2013 [in press]
27. S. Achelle, Y. Ramondenc, F. Marsais, and N. Plé Star- and banana-shaped oligomers with a pyrimidine core: synthesis and light-emitting properties Eur J Org Chem 2008 3129 3140
28. K. Itami, D. Yamazaki, and Ji Yoshida Pyrimidine-core extended π-systems: general synthesis and interesting fluorescent properties J Am Chem Soc 126 2004 15396 15397 (Pubitemid 39577470)
29. M.C. Bagley, Z. Lin, and S.J.A. Pope Barium manganate in microwave-assisted oxidation reactions: synthesis of solvatochromic 2,4,6-triarylpyrimidines Tetrahedron Lett 50 2009 6818 6822
30. S. Tumkevičius, A. Voitechovičius, and P. Adomėnas Synthesis of novel 2,4,6-triarylpyrimidines Chemija 23 2012 61 67
31. B. Liu, X.L. Hu, J. Liu, Y.D. Zhao, and Z.L. Huang Synthesis and photophysical properties of novel pyrimidine-based two-photon absorption chromophores Tetrahedron Lett 48 2007 5958 5962 (Pubitemid 47088689)
32. L. Li, J. Ge, H. Wu, Q.H. Xu, and S.Q. Yao Organelle-specific detection of phosphatase activities with two-photon fluorogenic probes in cells and tissues J Am Chem Soc 134 2012 12157 12167
33. S. Achelle, J.P. Malval, S. Aloïse, A. Barsella, A. Spangenberg, and L. Mager et al. Synthesis, photophysics and nonlinear optical properties of stilbenoid pyrimidine-based dyes bearing methylenepyran donor groups ChemphysChem 14 2013 2725 2736
34. S. Achelle, A. Barsella, C. Baudequin, B. Caro, and F. Robin-le Guen Synthesis and photophysical investigation of a series of push-pull arylvinyldiazine chromophores J Org Chem 77 2012 4087 4096
35. F. Castet, A. Pic, and B. Champagne Linear and nonlinear optical properties of arylvinyldiazine dyes: a theoretical investigation Dyes Pigments 110 2014 256 260
36. F. Bureš, O. Pytela, and F. Diederich Solvent effects on electronic absorption spectra of donor-substituted 11,11,12,12-tetracyano-9,10- anthraquinodimethanes (TCAQs) J Phys Org Chem 22 2009 155 162
37. F. Bureš, O. Pytela, M. Kivala, and F. Diederich Solvatochromism as an efficient tool to study N,N-dimethylamino- and cyano-substituted π-conjugated molecules with an intramolecular charge-transfer absorption J Phys Org Chem 24 2011 274 281
38. R. Lartia, C. Allain, G. Bordeau, F. Schmidt, Fiorini-Debuisschert, and F. Charra et al. Synthetic strategies to derivatizable triphenylamines displaying high two-photon absorption J Org Chem 73 2008 1732 1744 (Pubitemid 351438888)
39. C. Katan, F. Terenziani, O. Mongin, M.H.V. Werts, L. Porrès, and T. Pons et al. Effects of (multi)branching of dipolar chromophores on photophysical properties and two-photon absorption J Phys Chem A 109 2005 3024 3037 (Pubitemid 40496866)
40. -synthesis and solvatochromism of the fluorescence J Phys Org Chem 17 2004 1051 1056
41. A.R. Katritzky, D.C. Fara, H. Yang, and K. Tämm Quantitative measures of solvent polarity Chem Rev 104 2004 175 198
42. P.M. Mancini, C.G. Adam, G.G. Fortunato, and L.R. Vottero A comparison of nonspecific solvent scales. Degree of agreement of microscopic polarity values obtained by different measurement methods Arkivoc xvi 2007 266 280
43. C. Reichardt Solvatochromic dyes as solvent polarity indicators Chem Rev 94 1994 2319 2358 (Pubitemid 24987870)
44. T(30) values for 84 organic solvents J Phys Org Chem 27 2014 512 518
45. G. Taguchi System of experimental design 1987 Quality Resources Press White Plains, NJ
46. G. Taguchi Taguchi methods: orthogonal arrays and linear graphs (softcover edn) 1987 American Supplier Inst Dearborn, Mich, USA
47. P.J. Ross Taguchi techniques for quality engineering (hardcover edn) 1996 McGraw-Hill City of New York, New York, USA
48. A. Pourjavadi, M. Ayyari, and M.S. Amini-Fazl Taguchi optimized synthesis of collagen-g-poly(acrylic acid)/kaolin composite superabsorbent hydrogel Eur Polym J 44 2008 1209 1216
49. H.R.F. Masoumi, A. Kassim, M. Basri, and D.K. Abdullah Determining optimum conditions for lipase-catalyzed synthesis of triethanolamine (TEA)-based esterquat cationic surfactant by a Taguchi robust design method Molecules 16 2011 4672 4680
50. N. Drogat, M. Barrière, R. Granet, V. Sol, and P. Krausz High yield preparation of purpurin-18 from Spirulina maxima Dyes Pigments 88 2011 125 127
51. J. Kulhánek, F. Bureš, O. Pytela, T. Mikysek, J. Ludvík, and A. Růžička Puh-pull molecules with a systematically extended π-conjugated system featuring 4,5-dicyanoimidazole Dyes Pigments 85 2010 57 65
52. L. Chen, C.I. Chu, K.J. Chen, P.Y. Chen, S.F. Hu, and R.S. Liu An intelligent approach to the discovery of luminescent materials using combinatorial approach combined with Taguchi methodology Luminescence 26 2011 229 238
53. X. Zheng, B. Song, and B. Xu Palladium-catalyzed regioselective C-H Bond ortho-acetoxylation of arylpyridines 2010 4376 4380
54. L. Pascal, J.J. Vanden Eynde, Y. Van Haverbeke, P. Dubois, A. Michel, and U. Rant et al. Synthesis and characterization of novel para- and meta-phenylenevinylene derivatives: fine tuning of the electronic and optical properties of conjugated materials J Phys Chem B 106 2002 6442 6450 (Pubitemid 35281777)
55. S. Achelle, I. Nouira, B. Pfaffinger, Y. Ramondenc, N. Plé, and J. Rodríguez-López V-shaped 4,6-bis(arylvinyl)pyrimidine oligomers: synthesis and optical properties J Org Chem 74 2009 3711 3717