A straightforward synthesis and structure-activity relationship of highly efficient initiators for two-photon polymerization

Macromolecules

Volumn 46, Issue 2, 2013, Pages 352-361

  Li, Zhiquan ^a   Pucher, Niklas ^a   Cicha, Klaus ^a   Torgersen, Jan ^a   Ligon, Samuel C ^a   Ajami, Aliasghar ^a   Husinsky, Wolfgang ^a   Rosspeintner, Arnulf ^b   Vauthey, Eric ^b   Naumov, Sergej ^c   Scherzer, Tom ^c   Stampfl, Jürgen ^a   Liska, Robert ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF GENEVA   (Switzerland)

^c LEIBNIZ INSTITUTE OF SURFACE ENGINEERING IOM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3D STRUCTURE; BENZYLIDENE; DOUBLE BONDS; EMISSION QUANTUM YIELD; EXPERIMENTAL TEST; FIVE-MEMBERED RINGS; INITIATION EFFICIENCY; ONE-PHOTON EXCITATION; PHOTOINITIATORS; PROCESSING WINDOWS; QUANTUM-CHEMICAL CALCULATION; STRUCTURE ACTIVITY RELATIONSHIPS; SYSTEMATIC INVESTIGATIONS; TWO PHOTON; TWO PHOTON POLYMERIZATION; TWO-PHOTON ABSORPTIONS; WRITING SPEED;

CHEMICAL BONDS; CONDENSATION REACTIONS; KETONES; PHOTOPOLYMERIZATION; QUANTUM CHEMISTRY; QUANTUM YIELD; TWO PHOTON PROCESSES;

PHOTONS;

EID: 84872957174     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma301770a     Document Type: Article

References (66)

1. Serbin, J.; Gu, M. Adv. Mater. 2006, 18, 221-224
2. Sun, H.-B.; Matsuo, S.; Misawa, H. Appl. Phys. Lett. 1999, 74, 786-788
3. Krivec, S.; Matsko, N.; Satzinger, V.; Pucher, N.; Galler, N.; Koch, T.; Schmidt, V.; Grogger, W.; Liska, R.; Lichtenegger, H. C. Adv. Funct. Mater. 2010, 20, 811-819
4. Parthenopoulos, D. A.; Rentzepis, P. M. Science 1989, 245, 843-845
5. Pudavar, H. E.; Joshi, M. P.; Prasad, P. N.; Reinhardt, B. A. Appl. Phys. Lett. 1999, 74, 1338-1340
6. Maruo, S.; Nakamura, O.; Kawata, S. Opt. Lett. 1997, 22, 132-134
7. Malval, J.-P.; Jin, M.; Morlet-Savary, F.; Chaumeil, H. l. n.; Defoin, A.; Soppera, O.; Scheul, T.; Bouriau, M.; Baldeck, P. L. Chem. Mater. 2011, 23, 3411-3420
8. Belfield, K. D.; Ren, X.; Van Stryland, E. W.; Hagan, D. J.; Dubikovsky, V.; Miesak, E. J. J. Am. Chem. Soc. 2000, 122, 1217-1218
9. Belfield, K. D.; Schafer, K. J.; Liu, Y.; Liu, J.; Ren, X.; Stryland, E. W. V. J. Phys. Org. Chem. 2000, 13, 837-849
10. Schafer, K. J.; Hales, J. M.; Balu, M.; Belfield, K. D.; Van Stryland, E. W.; Hagan, D. J. J. Photochem. Photobiol., A 2004, 162, 497-502
11. Wang, X.; Jin, F.; Chen, Z.; Liu, S.; Wang, X.; Duan, X.; Tao, X.; Jiang, M. J. Phys. Chem. C 2011, 115, 776-784
12. Cumpston, B. H.; Ananthavel, S. P.; Barlow, S.; Dyer, D. L.; Ehrlich, J. E.; Erskine, L. L.; Heikal, A. A.; Kuebler, S. M.; Lee, I. Y. S.; McCord-Maughon, D.; Qin, J.; ckel, H.; Rumi, M.; Wu, X.-L.; Marder, S. R.; Perry, J. W. Nature 1999, 398, 51-54
13. Pucher, N.; Rosspeintner, A.; Satzinger, V.; Schmidt, V.; Gescheidt, G.; Stampfl, J.; Liska, R. Macromolecules 2009, 42, 6519-6528
14. Li, C.; Luo, L.; Wang, S.; Huang, W.; Gong, Q.; Yang, Y.; Feng, S. Chem. Phys. Lett. 2001, 340, 444-448
15. He, G. S.; Tan, L.-S.; Zheng, Q.; Prasad, P. N. Chem. Rev. 2008, 108, 1245-1330
16. Yagci, Y.; Jockusch, S.; Turro, N. J. Macromolecules 2010, 43, 6245-6260
17. Tian, Y.; Zhang, M.; Yu, X.; Xu, G.; Ren, Y.; Yang, J.; Wu, J.; Zhang, X.; Tao, X.; Zhang, S.; Jiang, M. Chem. Phys. Lett. 2004, 388, 325-329
18. Lemercier, G.; Martineau, C. c.; Mulatier, J.-C.; Wang, I. n.; Stéphan, O.; Baldeck, P.; Andraud, C. New J. Chem. 2006, 30, 1606-1613
19. Porshnev, Y. N.; Churkina, V. A.; Titov, V. V. Chem. Heterocycl. Compd. 1978, 14, 1070-1074
20. Lin, T.-C.; Hsu, C.-S.; Hu, C.-L.; Chen, Y.-F.; Huang, W.-J. Tetrahedron Lett. 2009, 50, 182-185
21. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066
22. Malval, J.-P.; Morlet-Savary, F.; Chaumeil, H.; Balan, L.; Versace, D.-L.; Jin, M.; Defoin, A. J. Phys. Chem. C 2009, 113, 20812-20821
23. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874-922
24. Huang, X.; Shi, Q.; Chen, W.-Q.; Zhu, C.; Zhou, W.; Zhao, Z.; Duan, X.-M.; Zhan, X. Macromolecules 2010, 43, 9620-9626
25. Monroe, B. M.; Smothers, W. K.; Keys, D. E.; Krebs, R. R.; Mickish, D. J.; Harrington, A. F.; Schicker, S. R.; Armstrong, M. K.; Chan, D. M. T.; Weathers, C. I. J. Imaging Sci. 1991, 35, 19-25
26. Wu, J.; Zhao, Y.; Li, X.; Shi, M.; Wu, F.; Fang, X. New J. Chem. 2006, 30, 1098-1103
27. Xue, J.; Zhao, Y.; Wu, J.; Wu, F. J. Photochem. Photobiol., A 2008, 195, 261-266
28. Xue, J.; Zhao, Y.; Wu, F.; Fang, D.-C. J. Phys. Chem. A 2010, 114, 5171-5179
29. Sarkisov, S. S.; Peterson, B. H.; Curley, M. J.; Nesterov, V. N.; Timofeeva, T.; Antipin, M.; Radovanova, E. I.; Leyderman, A.; Fleitz, P. A. J. Nonlinear Opt. Phys. 2005, 14, 21-40
30. Wang, P.; Du, W.; Wu, S. Huaxue Xuebao 1992, 50, 1140-1144
31. Yamashita, K.; Imahashi, S.; Ito, S. Dyes Pigm. 2008, 76, 748-753
32. Xing, J.-F.; Chen, W.-Q.; Dong, X.-Z.; Tanaka, T.; Fang, X.-Y.; Duan, X.-M.; Kawata, S. J. Photochem. Photobiol., A. 2007, 189, 398-404
33. Li, Z.; Siklos, M.; Pucher, N.; Cicha, K.; Ajami, A.; Husinsky, W.; Rosspeintner, A.; Vauthey, E.; Gescheidt, G.; Stampfl, J.; Liska, R. J. Polym. Sci., Polym. Chem. 2011, 49, 3688-3699
34. Olomucki, M.; Le Gall, J. Y. Bull. Soc. Chim. Fr. 1976, 9-10 (Pt. 2) 1467-1468
35. Doroshenko, A. O.; Grigorovich, A. V.; Posokhov, E. A.; Pivovarenko, V. G.; Demchenko, A. P.; Sheiko, A. D. Russ. Chem. B 2001, 50, 404-412
36. Rao, C. B.; Raju, P. V. N. Indian J. Chem. B 1984, 23, 321-327
37. Wallach Chem. Zentralbl. 1908, 79, 639
38. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
39. Becke, A. D. J. Chem. Phys. 1996, 104, 1040-1046
40. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
41. Jaguar, version 7.8, Schrodinger LLC, New York, 2010.
42. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454-464
43. Gaussian 03, Revision B.02: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Wallingford, CT, 2004.
44. Tannor, D. J. M.; Murphy, B.; Friesner, R.; Sitkoff, R. A.; Nicholls, D.; Ringnalda, A.; Goddard, W. A., III; Honig, B. J. Am. Chem. Soc. 1994, 116, 11875-11882
45. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098-16104
46. ChemBio3D Ultra, version 12.0, CambridgeSoft, 1986-2009.
47. Gardecki, J. A.; Maroncelli, M. Appl. Spectrosc. 1998, 52, 1179-1189
48. Van Gompel, J. A.; Schuster, G. B. J. Phys. Chem. 1989, 93, 1292-1295
49. Valeur, B. Molecular Fluorescence: Principles and Applications; Wiley-VCH: Weinheim, 2001; p 161.
50. An, L. T.; Zou, J. P.; Zhang, L. L. Catal. Commun. 2008, 9, 349-354
51. Watanabe, K.; Imazawa, A. Bull. Chem. Soc. Jpn. 1982, 55, 3208-3211
52. Klessinger, M.; Michl, J. Lichtabsorption und Photochemie organischer Moleküle; VCH Verlagsgesellschaft: Weinheim, 1989; p 255.
53. El-Sayed, M. A. J. Chem. Phys. 1963, 38, 2834-2838
54. Valeur, B.; Weber, G. Photochem. Photobiol. 1977, 25, 441-444
55. Zou, Q.; Zhao, Y.; Makarov, N. S.; Campo, J.; Yuan, H.; Fang, D.-C.; Perry, J. W.; Wu, F. Phys. Chem. Chem. Phys. 2012, 14 (33) 11743-11752
56. Birks, J. B. Photophysics of Aromatic Molecules; Wiley Monographs in Chemical Physics; Wiley-Interscience: London, 1970; p 51.
57. Angulo, G.; Grampp, G.; Rosspeintner, A. Spectrochim. Acta, Part A 2006, 65, 727-731
58. Marcus, Y. The Properties of Solvents; Wiley Series in Solution Chemistry; John Wiley & Sons Ltd.: Weinheim, 1998; Vol. 4.
59. Sheik-Bahae, M.; Said, A. A.; Wei, T. H.; Wu, Y. Y.; Hagan, D. J.; Soileau, M. J.; Van Stryland, E. W. Proc. SPIE 1990, 1148, 41-51
60. Yuan, H.; Zhao, Y.; Wu, F. Chem. Mater. 2012, 24, 1371-1377
61. Xing, J.-F.; Dong, X.-Z.; Chen, W.-Q.; Duan, X.-M.; Takeyasu, N.; Tanaka, T.; Kawata, S. Appl. Phys. Lett. 2007, 90, 131106/1-131106/3
62. Xing, J.-F.; Chen, W.-Q.; Gu, J.; Dong, X.-Z.; Takeyasu, N.; Tanaka, T.; Duan, X.-M.; Kawata, S. J. Mater. Chem. 2007, 17, 1433-1438
63. Xing, J.-F.; Zheng, M.-L.; Chen, W.-Q.; Dong, X.-Z.; Takeyasu, N.; Tanaka, T.; Zhao, Z.-S.; Duan, X.-M.; Kawata, S. Phys. Chem. Chem. Phys. 2012, 14, 15785-15792
64. Ovsianikov, A.; Schlie, S.; Ngezahayo, A.; Haverich, A.; Chichkov, B. N. J. Tissue Eng. Regener. Med. 2007, 1, 443-449
65. Mendonca, C. R.; Correa, D. S.; Baldacchini, T.; Tayalia, P.; Mazur, E. Appl. Phys. A: Mater. Sci. Process. 2008, 90 (4) 633-636
66. Farsari, M.; Filippidis, G.; Sambani, K.; Drakakis, T. S.; Fotakis, C. J. Photochem. Photobiol., A 2006, 181, 132-135