Synthesis of novel oxidizable polymerization sensitizers based on the dithiinoquinoxaline skeleton

Dyes and Pigments

Volumn 92, Issue 3, 2012, Pages 1300-1307

  Podsiadły, Radosław ^a   Sokołowska, Jolanta ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

DFT calculations; Dithiinoquinoxaline dyes; Free radical polymerization; Oxidizable sensitization; Photoinduced electron transfer; Synthesis

Indexed keywords

CHEMICAL IONIZATION; DFT CALCULATION; DITHIINOQUINOXALINE DYES; ELECTRON DONATING PROPERTIES; EMISSION SPECTRUMS; FREE ENERGY CHANGE; H NMR SPECTROSCOPY; INITIATOR SYSTEMS; INTERMOLECULAR ELECTRON TRANSFER; LIMITING STEP; MASS SPECTROSCOPY; OXIDIZABLE SENSITIZATION; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOINITIATORS; SPECTRAL PROPERTIES; TITLE COMPOUNDS;

ATOM TRANSFER RADICAL POLYMERIZATION; ELECTRON TRANSITIONS; EMISSION SPECTROSCOPY; FREE RADICALS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOPOLYMERIZATION; QUANTUM YIELD;

FREE RADICAL POLYMERIZATION;

EID: 80054070339     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.09.006     Document Type: Article

References (30)

1. W. Schnabel Polymers and light. Fundamentals and technical application 2007 Wiley-VCH Weinheim pp. 305-33
2. Y. Yagci, S. Jockusch, and J.N. Turro Photoinitiated polymerization: advances, challenges, and opportunities Macromolecules 43 2010 6245 6260
3. B. Przyjazna, Z. Kucybała, and J. Pczkowski Development of new dyeing photoinitiators based on 6H-indolo[2,3-b]quinoxaline skeleton Polymer 45 2004 2559 2566 (Pubitemid 38379606)
4. J. Kabatc Multicationic monomethine dyes as sensitizers in two- and three-component photoinitiating systems for multiacrylate monomers J Photochem Photobiol A Chem 214 2010 74 85
5. J. Kabatc, and J. Pczkowski Monomeric asymmetric two- and three-cationic monomethine cyanine dyes as novel photoinitiators for free-radical polymerization Dyes Pigm 86 2010 133 142
6. O.I. Tarzi, X. Allonas, C. Ley, and J.P. Fouassier Pyrromethene derivatives in three-component photoinitiating systems for free radical photopolymerization J Polym Sci Part A Polym Chem 48 2010 2594 2603
7. C. Grotzinger, D. Burget, P. Jacques, and J.P. Fouassier Photopolymerization reaction initiated by a visible light photoinitiating system: dye/amine/bis(trichloromethyl)-substituted-1,2,5-triazine Macromol Chem Phys 202 2001 3513 3522 (Pubitemid 135749149)
8. R. Podsiadły Photoreaction and photopolymerization studies on fluoflavin dye-pyridinium salt systems J Photochem Photobiol A Chem 198 2008 60 68
9. J. Kolińska, R. Podsiadły, and J. Sokołowska Naphthoylenebenzimidazolone sensitisers for photo-oxidisable free radical polymerisation with the aid of pyridinium salts Coloration Technol 124 2008 341 347
10. R. Podsiadły, A.M. Szymczak, and K. Podemska The synthesis of novel, visible-wavelength, oxidizable polymerization sensitizers based on the 8-halogeno-5,12-dihydroquinoxalino[2,3-b]quinoxaline skeleton Dyes Pigm 82 2009 365 371
11. R. Podsiadły The synthesis of novel, visible-wavelength oxidizable polymerization sensitizers based on the 5,12-dihydroquinoxalino[2,3-b] pyridopyrazine skeleton Dyes Pigm 80 2009 86 92
12. R. Podsiadły Synthesis and photochemical reaction of novel, visible-wavelength oxidizable polymerization sensitizer based on the 12H-quinoxalino[2,3-b][1,4]benzothiazine skeleton J Photochem Photobiol A Chem 202 2009 115 121
13. T. Nashinaga, A. Wakamiya, and K. Komatsu The first isolation of the hexafluoroantimonate salt of a 1,4-dithiin radical cation stabilized by bicyclo[2.2.2]octene annelation Tetrahedron Lett 40 1999 4375 4378 (Pubitemid 29251449)
14. S.R. Shin, and H.J. Shine Reactions of phenols with thianthrene cation radical J Org Chem 57 1992 2706 2710
15. K. Iwai, and H.J. Shine Ion radicals. 46. Reactions of the adducts of thianthrene and phenoxathiin cation radicals and cyclohexene with nucleophiles J Org Chem 46 1981 271 276
16. W. Zhao, and H.J. Shine Reaction of thianthrene cation radical with alcohols: isolation and chemistry of 5-cyclohexyloxythianthreniumyl perchlorate Tetrahedron Lett 37 1996 1749 1750 (Pubitemid 26088776)
17. A. Houmam, D. Shukla, H.B. Kraatz, and D.D.M. Wayner Electrosynthesis of mono- and bisthianthrenium salts J Org Chem 64 1999 3342 3345
18. P.J. Skabara, R. Berridge, K. Prescott, L.M. Goldenberg, E. Orti, and R. Viruela Experimental and theoretical studies into structural perturbation between neutral, oxidized and reduced forms of 1,4-dithiinoquinoxaline derivatives J Mater Chem 10 2000 2448 2457
19. Y.Z. Voloshin, A.S. Belov, A.Y. Lebedev, O.A. Varzatskii, M.Y. Antipin, and Z.A. Starikova Synthesis and structure of the first ribbed-functionalized quinoxaline clathronchelate: design of cage complexes for efficient intercalation into DNA structure Russ Chem Bull Int Ed 53 2004 1218 1222 (Pubitemid 39273673)
20. M. Matsuoka, A. Iwamoto, N. Furukawa, and T. Kitao Syntheses of polycyclic 1,4-dithiines and related heterocycles J Heterocyclic Chem 29 1992 439 443
21. W.B. Leighton, and G.S. Forbes Precision actinometry with uranyl oxalate J Am Chem Soc 52 1930 3139 3152
22. T. Karstens, and K. Kobs Rhodamine B and rhodamine 101 as reference substances for fluorescence quantum yield measurements J Phys Chem 84 1980 1871 1872
23. D. Avci, J. Nobles, and L.J. Mathias Synthesis and photopolymerization kinetics of new flexible diacrylate and dimethacrylate crosslinkers based on C18 diacid Polymer 44 2003 963 968 (Pubitemid 36133682)
24. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange J Chem Phys 98 1993 5648 5652
25. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys Rev B 37 1988 785 789
26. Gaussian 03, revision B.01 2003 Gaussian, Inc. Pittsburgh PA
27. D. Rehm, and A. Weller Kinetics of fluorescence quenching by electron and H-atom transfer Isr J Chem 8 1970 259 271
28. H. Spreitzer, and J. Daub Multi-mode switching based on dihydroazulene/vinylheptafulvene photochromism: synergism of photochromism and redox switching in heteroaryl-functionalized systems Chem Eur J 2 1996 1150 1158
29. L. Engman, J. Hellberg, C. Ishag, and S. Söderholm New alkoxylated dibenzo[1,4]dichalco-genines as donors for low-dimensinal materials: electrochemistry and cation-radical salts J Chem Soc Perkin Trans 1 8 1988 2095 2101
30. J. Pczkowski, and Z. Kucybała Generalization of the kinetic scheme for dye-photosensitized free-radical polymerization initiating system via an intermolecular electron-transfer process. Application of Marcus theory Macromolecules 28 1995 269 273