Extended mechanistic aspects on photoinitiated polymerization of 1,6-hexanediol diacrylate by hexaarylbisimidazoles and heterocyclic mercapto compounds

Photochemical and Photobiological Sciences

Volumn 13, Issue 5, 2014, Pages 789-798

  Berdzinski, Stefan ^a   Strehmel, Nadine ^b   Lindauer, Heike ^c   Strehmel, Veronika ^a   Strehmel, Bernd ^a  

^a NIEDERRHEIN UNIVERSITY OF APPLIED SCIENCES   (Germany)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^c Thuringian Institute for Textile and Plastics Research   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,6-HEXANEDIOL DIACRYLATE; ACRYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; THIOL DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; PHOTOCHEMISTRY; PHOTOLYSIS; POLYMERIZATION; SYNTHESIS; ULTRAVIOLET RADIATION;

ACRYLATES; ELECTROCHEMICAL TECHNIQUES; HETEROCYCLIC COMPOUNDS; IMIDAZOLES; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; PHOTOLYSIS; POLYMERIZATION; SULFHYDRYL COMPOUNDS; ULTRAVIOLET RAYS;

EID: 84898791214     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c3pp50379h     Document Type: Article

References (53)

1. R. Dessauer, Photochemistry, History and Commercial Applications of Hexaarylbiimidazoles: All about HABIs, Elsevier, 2006
2. R. Dessauer The invention of Dylux instant-access imaging materials and the development of HABI chemistry-a personal history Adv. Photochem. 2005 28 129 261
3. B. M. Monroe G. C. Weed Photoinitiators for free-radical-initiated photoimaging systems Chem. Rev. 1993 93 435 448
4. V. Strehmel J. V. Whishart D. A. Polyansky B. Strehmel Recombination of Photogenerated Lophyl Radicals in Imidazolium-Based Ionic Liquids ChemPhysChem 2009 10 3112 3118
5. S. Berdzinski J. Horst P. Strassburg V. Strehmel Recombination of Lophyl Radicals in Pyrrolidinium-Based Ionic Liquids ChemPhysChem 2013 24 1751 1760
6. V. Strehmel Radicals in ionic liquids ChemPhysChem 2012 13 1649 1663
7. K. Mutoh M. Sliwa J. Abe Rapid Fluorescence Switching by Using a Fast Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimer J. Phys. Chem. C 2013 117 4808 4814
8. S. Hatano T. Horino A. Tokita T. Oshima J. Abe Unusual Negative Photochromism via a Short-Lived Imidazolyl Radical of 1,1′-Binaphthyl- Bridged Imidazole Dimer J. Am. Chem. Soc. 2013 135 3164 3172
9. K. Fujita S. Hatano D. Kato J. Abe Photochromism of a radical diffusion-inhibited hexaarylbiimidazole derivative with intense coloration and fast decoloration performance Org. Lett. 2008 10 3105 3108
10. K. Mutoh E. Nakano J. Abe Spectroelectrochemistry of a Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimer: Clarification of the Electrochemical Behavior of HABI J. Phys. Chem. A 2012 116 6792 6797
11. A. Kikuchi T. Iyoda J. Abe Electronic structure of light-induced lophyl radical derived from a novel hexaarylbiimidazole with pi-conjugated chromophore Chem. Commun. 2002 1484 1485
12. H. Sato K. Kasatani S. Murakami Magnetic field effects on the photochromism of hexaphenylbiimidazolyl Chem. Phys. Lett. 1988 151 97 101
13. Y. Sakaino Structures and chromotropic properties of imidazole derivatives produced from 3,6-bis(4,5-diphenyl-2H-imidazol-2-ylidene)cyclohexa- 1,4-diene J. Chem. Soc., Perkin Trans. 1 1983 1063 1066
14. Y. Sakaino H. Kakisawa T. Kusumi Synthesis of new photochromic compounds from the dimer of arylphenanthroimidazoles J. Heterocycl. Chem. 1975 12 953 956
15. K. Maeda T. Hayashi Mechanism of photochromism, thermochromism, and piezochromism of dimers of triarylimidazolyl Bull. Chem. Soc. Jpn. 1970 43 429 438
16. T. Shida K. Maeda T. Hayashi Optical and E.S.R. studies on triphenylimidazolyl radicals produced by photolysis and radiolysis at low temperatures Bull. Chem. Soc. Jpn. 1969 42 3044
17. M. A. J. Wilks M. R. Willis Kinetics of the photochromic decay reaction of 2,2′,4,4′,5,5′-hexaphenylbiimidazolyl J. Chem. Soc. B 1968 1526 1529
18. T. Hayashi K. Maeda T. Kanaji The mechanism of the photochromism and thermochromism of 2,2′,4,4′,5,5′-hexaphenyl-1,1′- biimidazolyl in a solid state Bull. Chem. Soc. Jpn. 1965 38 857
19. J. V. Caspar I. V. Khudyakov N. J. Turro G. C. Weed ESR Study of Lophyl Free Radicals in Dry Films Macromolecules 1995 28 636 641
20. X. Z. Qin A. Liu A. D. Trifunac V. V. Krongauz Photodissociation of hexaarylbiimidazole. 1. Triplet-state formation J. Phys. Chem. 1991 95 5822 5826
21. A. D. Liu A. D. Trifunac V. V. Krongauz Photodissociation of hexaarylbiimidazole. 2. Direct and sensitized dissociation J. Phys. Chem. 1992 96 207 211
22. T. Matsuura Y. Ito I. Saito Photoinduced reactions. LXVIII. Photochemical dehydrogenation of imidazolines to imidazoles Bull. Chem. Soc. Jpn. 1973 46 3805 3809
23. T. Hayashi K. Maeda Mechanism of reversible photochemical color change of bis(triphenylimidazolyl) at low temperature Bull. Chem. Soc. Jpn. 1967 40 2990
24. J. Abe T. Sano M. Kawano Y. Ohashi M. M. Matsushita T. Iyoda EPR and density functional studies of light-induced radical pairs in a single crystal of a hexaarylbiimidazolyl derivative Angew. Chem., Int. Ed. 2001 40 580 582
25. M. Schrödner H. Schache H. Lindauer R. Schrödner A. Konkin Oscillations of the lophyl radical concentration during the photo-decomposition of o-Cl-hexaarylbisimidazole J. Photochem. Photobiol., A 2012 233 60 64
26. A. Ibrahim C. Ley X. Allonas O. I. Tarzi A. Chan Yong C. Carre R. Chevallier Optimization of a photopolymerizable material based on a photocyclic initiating system using holographic recording Photochem. Photobiol. Sci. 2012 11 1682 1690
27. X. Hu H. Zhang G. Zhang Y. Sheng Y. Wang R. Zhao Water-resisting compound red-sensitive photopolymer: mechanism and optimization of components Proc. SPIE-Int. Soc. Opt. Eng. 2005 5636 635 645
28. C. Zhang J. Zhao J. He L. Li Y. Yang Photoinitiating systems and photopolymer materials for holography Proc. SPIE-Int. Soc. Opt. Eng. 1998 3559 81 87
29. D. F. Eaton A. G. Horgan J. P. Horgan Mechanism of coinitiation of photopolymerization of methyl methacrylate by hexaarylbiimidazole-hydrogen atom donor combinations. The role of electron transfer versus direct hydrogen atom abstraction J. Photochem. Photobiol., A 1991 58 373 391
30. X. Li Y. Zhao J. Wu M. Shi F. Wu Two-photon photopolymerization using novel asymmetric ketocoumarin derivatives J. Photochem. Photobiol., A 2007 190 22 28
31. J. Xue Y. Zhao J. Wu F. Wu Novel benzylidene cyclopentanone dyes for two-photon photopolymerization J. Photochem. Photobiol., A 2008 195 261 266
32. J. Lalevee F. Morlet-Savary R. M. El X. Allonas J. P. Fouassier Thiyl radical generation in thiol or disulfide containing photosensitive systems Macromol. Chem. Phys. 2009 210 311 319
33. S. Suzuki P. Emilie T. Urano S. Takahara T. Yamaoka Three-component photoradical initiating system-the effect of 2-mercaptobenzothiazole as a coinitiator in polymer matrix Polymer 2005 46 2238 2243
34. S. Suzuki T. Urano K. Ito T. Murayama I. Hotta S. Takahara T. Yamaoka Pyrromethene dye sensitized photopolymer and the application to visible laser direct imaging J. Photopolym. Sci. Technol. 2004 17 125 130
35. S. Suzuki T. Urano N. Miyagawa S. Takahara T. Yamaoka Three-component radical photoinitiating systems-the effect of the accelerator J. Photopolym. Sci. Technol. 2001 14 259 262
36. T. Urano H. Ito K. Takahama T. Yamaoka Photopolymerization mechanisms of acrylates in poly(methyl methacrylate) films Polym. Adv. Technol. 1999 10 201 205
37. T. Urano, H. Ito, K. Takahama and T. Yamaoka, Double-amplified photoinitiator systems, RadTech'98 North America UV/EB Conference Proceedings, Chicago, April 19-22, 1998, 1998, 734 745
38. Q. Q. Zhu M. Fink F. Seitz S. Schneider W. Schnabel On the photolysis of bis[2-(o-chlorophenyl)-4,5-diphenylimidazole] sensitized by 2- isopropylthioxanthone or Michler's ketone J. Photochem. Photobiol., A 1991 59 255 263
39. M. Jin J.-P. Malval D.-L. Versace F. Morlet-Savary H. Chaumeil A. Defoin X. Allonas J.-P. Fouassier Two-photon absorption and polymerization ability of intramolecular energy transfer based photoinitiating systems Chem. Commun. 2008 6540 6542
40. X. Allonas J. P. Fouassier M. Kaji Y. Murakami Excited state processes in a four-component photosensitive system based on a bisimidazole derivative Photochem. Photobiol. Sci. 2003 2 224 229
41. X. Allonas J. P. Fouassier M. Kaji M. Miyasaka T. Hidaka Two and three component photoinitiating systems based on coumarin derivatives Polymer 2001 42 7627 7634
42. X. Allonas J. P. Fouassier M. Kaji M. Miyasaka On the ability of coumarin derivatives to interact with photoinitiators J. Photopolym. Sci. Technol. 2000 13 237 242
43. T. Urano Sensitizer dyes and sensitization mechanisms in photopolymer coating layer Proc. SPIE-Int. Soc. Opt. Eng. 2002 4659 420 427
44. T. Urano M. Ishikawa Y. Sato H. Itoh Sensitizer dyes and sensitization mechanisms in photopolymer coating layer II J. Photopolym. Sci. Technol. 1999 12 711 716
45. T. Urano E. Hino H. Ito M. Shimizu T. Yamaoka Study of radical generated from coumarin dye-sensitized photoinitiator systems in high-speed photopolymer coating layers using laser flash photolysis Polym. Adv. Technol. 1998 9 825 830
46. T. Urano H. Nagasaka S. Shimizu H. Ito M. Shimizu S. Takahara T. Yamaoka Laser-flash photolysis in high-speed photopolymer coating layers containing carbonylbiscoumarin dyes and 2,2′-bis(2-chlorophenyl)-4,4′,5, 5′-tetraphenyl-1,1′-bi-1H-imidazole Bull. Chem. Soc. Jpn. 1997 70 1659 1664
47. T. Urano H. Nagasaka M. Shimizu S. Takahara T. Yamaoka Laser flash photolysis in high-speed photopolymer coating layers: effects of incorporating dimethyl phthalate as a plasticizer into coating formulation Bull. Chem. Soc. Jpn. 1996 69 693 700
48. T. Urano H. Nagasaka M. Tsuchiyama S. Shimizu K. Kawazoe M. Shimizu T. Yamaoka Laser flash photolysis in high-speed photopolymer coating layers Bull. Chem. Soc. Jpn. 1995 68 1661 1668
49. W. A. Green, Industrial Photoinitiators: A Technical Guide, CRC Press, Boca Raton, 2010
50. H.-J. Timpe B. Strehmel Lichtinduzierte Polymer- und Polymerisationsreaktionen. 44. Zur Kinetik der radikalischen Photopolymerisation mehrfunktionellerAcrylate in polymeren Bindemitteln Makromol. Chem. 1991 192 779 791
51. M. Muneer P. V. Kamat M. V. George Electron transfer reactions. Reaction of nitrogen heterocycles with potassium Can. J. Chem. 1990 68 969 975
52. E. W. Oliver D. H. Evans J. V. Caspar Electrochemical studies of a hexaarylbiimidazole J. Electroanal. Chem. 1996 403 153 158
53. I. Fleming and J. Podlech, Molekülorbitale und Reaktionen organischer Verbindungen, Wiley-VCH, Weinheim, 2012