One- and two-photon photochemistry and photophysics of poly(arylenevinylene)s containing a biphenyl moiety

ChemPhysChem

Volumn 6, Issue 2, 2005, Pages 267-276

  Strehmel, Veronika ^a   Sarker, Ananda M ^b   Lahti, Paul M ^b   Karasz, Frank E ^b   Heydenreich, Matthias ^a   Wetzel, Hendrik ^c   Haebel, Sophie ^a   Strehmel, Bernd ^a,d  

^a UNIVERSITY OF POTSDAM   (Germany)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

^c FRAUNHOFER INSTITUTE FOR APPLIED POLYMER RESEARCH   (Germany)

^d Kodak Polychrome Graphics   (Germany)

Author keywords

Conjugation; Fluorescence; Photochemistry; Photophysics; Two photon absorption

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; CHROMOPHORES; DESORPTION; FLUORESCENCE; GEL PERMEATION CHROMATOGRAPHY; PHOTOCHEMICAL REACTIONS; PHOTONS; PHOTOPHYSICS; TWO PHOTON PROCESSES;

CONJUGATION; EFFECTIVE CONJUGATION LENGTH; EXCITED-STATE PROPERTIES; GEL PERMEATION CHROMATOGRAPHY (GPC); HETERONUCLEAR MULTIPLE QUANTUM COHERENCES; INTRAMOLECULAR PHOTOCYCLIZATION; PHOTOPHYSICAL PROPERTIES; TWO PHOTON ABSORPTION;

EXCITED STATES;

BIPHENYL DERIVATIVE; POLYVINYL DERIVATIVE; POLY[(2,5 DIHEXYLOXY 4 PHENYLENEVINYLENE) ALT (2,2' BIPHENYLENEVINYLENE)]; POLY[(2,5 DIHEXYLOXY 4 PHENYLENEVINYLENE) ALT (2,2' DIHEXYLOXY 3,3' BIPHENYLENEVINYLENE)]; POLY[(2,5 DIHEXYLOXY 4 PHENYLENEVINYLENE) ALT (4,4' DIHEXYLOXY 3,3' BIPHENYLENEVINYLENE)]; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; CYCLIZATION; ELECTRON TRANSPORT; ENERGY; GEL PERMEATION CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PHOTON; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 15044365429     PISSN: 14394235     EISSN: None     Source Type: Journal    
DOI: 10.1002/cphc.200400407     Document Type: Article

References (90)

1. M. Göppert-Mayer, Ann. Phys. 1931, 273.
2. W. Kaiser, C. G. B. Garrett, Phys. Rev. Lett. 1962, 7, 229.
3. a) W. M. McClain, R. A. Harris in Excited States, Vol. 3 (Ed.: E. C. Lim), Academic Press, New York, 1977, p. 1;
4. b) W. M. McClain, Acc. Chem. Res. 1974, 7, 129;
5. c) B. Dick, H. Gonska, G. Hohlneicher, Ber. Bunsenges. Phys. Chem. 1981, 85, 746;
6. d) D. M. Friedrich, J. Chem. Educ. 1982, 59, 472;
7. e) L. Goodman, R. P. Rava, Acc. Chem. Res. 1984, 17, 250;
8. f) B. Dick, R. M. Hochstrasser, H. P. Trommsdorff in Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 2 (Eds.: D. S. Chemla, D. S. Zyss), Academic Press, Inc., New York, 1987, p. 1 59;
9. g) M. T. Allen, D. G. Whitten, Chem. Rev. 1989, 89, 1691.
10. a) T. C. Lin, S.-J. Chung, K. S. Kim, X. Wang, G.-S. He, J. Swiatkiewcz, H. E. Pudavar, P. N. Prasad in Polymers for Photonics Applications II, Vol. 161 (Ed.: K.-S. Lee), Springer, Berlin, 2003, p. 157;
11. b) L. Levy, Y. Sahoo, K.-S. Kim, E. J. Bergey, P. N. Prasad, Chem. Mater. 2002, 14, 3715;
12. b) B. A. Holm, E. J. Bergey, T. De, D. J. Rodman, R. Kapoor, L. Levy, C. S. Friend, P. N. Prasad, Mol. Cryst. Liq. Cryst. 2002, 374, 589;
13. c) H. S. Nalwa, S. Miyata, Nonlinear Optics of Organic Molecules and Polymers, CRC Press, Inc., Boca Raton, Florida, 1997;
14. d) J. D. Bhawalkar, G. S. He, P. N. Prasad, Rep. Prog. Phys. 1997, 59, 1041.
15. a) C. Xu, W. W. Webb in Topics in Fluorescence Spectroscopy, Vol. V (Ed.: J. R. Lakowicz), Kluwer Academic Publishers, 1997, p. 471;
16. b) L. J. Krebs, X. Wang, A. Nagy, A. V. Schally, P. N. Prasad, C. Liebow, Int. J. Oncol. 2002, 21, 1325;
17. c) E. J. Bergey, L. Levy, X. Wang, L. J. Krebs, M. Lal, K.-S. Kim, S. Pakatchi, C. Liebow, P. N. Prasad, Biomed. Microdevices 2002, 4, 293;
18. d) X. Wang, H. E. Pudavar, R. Kapoor, L. J. Krebs, E. J. Bergey, C. Liebow, P. N. Prasad, A. Nagy, A. V. Schally, J. Biomed. Opt. 2001, 6, 319;
19. e) L. J. Krebs, X. Wang, H. E. Pudavar, E. J. Bergey, A. V. Schally, A. Nagy, P. N. Prasad, C. Liebow, Cancer Res. 2000, 60, 4194;
20. f) M. H. Blanchard-Desce, L. Ventelon, S. Charier, L. Moreaux, J. Mertz, Proc. SPIE-Int. Soc. Opt. Eng. 2001, 4461, 20.
21. a) H.-B. Sun, M. Maeda, K. Takada, J. W. M. Chon, M. Gu, S. Kawata, Appl. Phys. Lett. 2003, 83, 819;
22. b) T. Watanabe, M. Akiyama, K. Totani, S. M. Kuebler, F. Stellari, W. Wenseleers, K. Braun, S. R. Marder, J. W. Perry, Adv. Funct. Mater. 2002, 12, 611;
23. c) T. Tanaka, H.-B. Sun, S. Kawata, Appl. Phys. Lett. 2002, 80, 312;
24. d) S. Kawata, H.-B. Sun, J. Photopolym. Sci. Technol. 2002, 15, 471;
25. e) L. Luo, C. Li, S. Wang, W. Huang, C. Wu, H. Yang, H. Jiang, Q. Gong, Y. Yang, S. Feng, J. Opt. A 2001, 3, 489;
26. f) K. D. Belfield, X. B. Ren, E. W. Van Stryland, D. J. Hagan, V. Dubikovsky, E. J. Miesak, J. Am. Chem. Soc. 2000, 122, 1217;
27. g) B. H. Cumpston, S. P. Ananthavel, S. Barlow, D. L. Dyer, J. E. Ehrlich, L. L. Erskine, A. A. Heikal, S. M. Kuebler, I. Y. S. Lee, D. McCord-Maughon, J. Qin, H. Rockel, M. Rumi, X.-L. Wu, S. R. Marder, J. W. Perry, Nature 1999, 398, 51;
28. h) S. M. Kuebler, K. L. Braun, W. Zhou, J. K. Cammack, T. Yu, C. K. Ober, S. R. Marder, J. W. Perry, J. Photochem. Photobiol. A 2003, 158, 163;
29. S. M. Kuebler, M. Rumi, T. Watanabe, K. Braun, B. H. Cumpston, A. A. Heikal, L. L. Erskine, S. Thayumanavan, S. Barlow, S. R. Marder, J. W. Perry, J. Photopolym. Sci. Technol. 2001, 14, 657.
30. a) P. Boffi, D. Picchin, M. C. Ubaldi, Infrared Holography for Optical Communications, Vol. 86, Springer, Berlin, 2003;
31. b) D. A. Parthenopoulus, P. M. Rentzepis, Science 1989, 245, 843;
32. c) S. M. Kirkpatrick, J. W. Baur, C. M. Clark, L. R. Denny, D. W. Tomlin, B. R. Reinhardt, R. Kannan, M. O. Stone, Appl. Phys. A 1999, 69, 461.
33. a) B. A. Reinhardt, Photonics Sci. News 1999, 4, 21;
34. b) P. N. Prasad, J. D. Bhawalkar, N. D. Kumar, M. Lal, Macromol. Symp. 1997, 118, 467;
35. c) J. D. Bhawalkar, N. D. Kumar, C. F. Zhao, P. N. Prasad, J. Clin. Laser Med. Sur. 1997, 15, 201.
36. -1.
37. a) M. Albota, D. Beljonne, J.-L. Bredas, J. E. Ehrlich, J.-Y. Fu, A. A. Heikal, S. E. Hess, T. Kogej, M. D. Levin, S. R. Marder, D. McCord-Maughon, J. W. Perry, H. Rockel, M. Rumi, G. Subramaniam, W. W. Webb, X.-L. Wu, C. Xu, Science 1998, 281, 1653;
38. b) M. Rumi, J. E. Ehrlich, A. A. Heikal, J. W. Perry, S. Barlow, Z. Hu, D. McCord-Maughon, T. C. Parker, H. Roeckel, S. Thayumanavan, S. R. Marder, D. Beljonne, J.-L. Bredas, J. Am. Chem. Soc. 2000, 122, 9500;
39. c) S. J. K. Pond, M. Rumi, M. D. Levin, T. C. Parker, D. Beljonne, M. W. Day, J.-L. Bredas, S. R. Marder, J. W. Perry, J. Phys. Chem. A. 2002, 106, 11 470;
40. d) S. J. Chung, T. C. Lin, K. S. Kim, G. S. He, J. Swiatkiewicz, P. N. Prasad, G. A. Baker, F. V. Bright, Chem. Mater. 2001, 13, 4071;
41. e) B. R. Cho, M. J. Piao, K. H. Son, S. H. Lee, S. J. Yoon, S.-J. Jeon, M. Cho, Chem. Eur. J. 2002, 8, 3907;
42. f) S.-J. Chung, K.-S. Kim, T.-C. Lin, G. S. He, J. Swiatkiewicz, P. N. Prasad, J. Phys. Chem. B 1999, 103, 10 741;
43. g) B.A. Reinhardt, L. L. Brott, S. J. Clarson, A. G. Dillard, J. C. Bhatt, R. Kannan, L. Yuan, G. S. He, P. N. Prasad, Chem. Mater. 1998, 10, 1863;
44. h) L. Ventelon, L. Moreaux, J. Mertz, M. Blanchard-Desce, Synth. Met. 2002, 127, 17;
45. i) O. Mongin, L. Porres, L. Moreaux, J. Mertz, M. Blanchard-Desce, Org. Lett. 2002, 4, 719;
46. j) L. Ventelon, S. Charier, L. Moreaux, J. Mertz, M. Blanchard-Desce, Angew. Chem. Int. Ed. 2001, 40, 2098; Angew. Chem. 2001, 113, 2156;
47. j) L. Ventelon, S. Charier, L. Moreaux, J. Mertz, M. Blanchard-Desce, Angew. Chem. Int. Ed. 2001, 40, 2098; Angew. Chem. 2001, 113, 2156;
48. k) M. Barzoukas, M. Blanchard-Desce, J. Chem. Phys. 2000, 113, 3951.
49. B. Strehmel, A. M. Sarker, H. Detert, ChemPhysChem 2003, 4, 249.
50. a) A. Hohenau, C. Cagran, G. Kranzelbinder, U. Scherf, G. Leising, Adv. Mater. 2001, 13, 1303;
51. b) R. Anemian, P. L. Baldeck, C. Andraud, Mol. Cryst. Liq. Cryst. 2002, 374, 335;
52. c) P. Najechalski, Y. Morel, O. Stephan, P. L. Baldeck, Chem. Phys. Lett. 2001, 343, 44;
53. d) L. Moroni, P. R. Salvi, C. Gellini, G. Dellipiane, D. Comoretto, C. Cuniberti, J. Phys. Chem. A 2001, 105, 7759;
54. e) S. J. Chung, G. S. Maciel, H. E. Pudavar, T. C. Lin, G. S. He, J. Swiatkiewicz, P. N. Prasad, D. W. Lee, J. I. Jin, J. Phys. Chem. A 2002, 106, 7512;
55. f) T. Cassano, R. Tommasi, M. Ferrara, F. Babudri, G. M. Farinola, F. Naso, Chem. Phys. 2001, 272, 111;
56. g) R. K. Meyer, R. E. Benner, Z. V. Vardeny, M. Liess, M. Ozaki, K. Yoshino, Y. Ding, T. Barton, Synth. Met. 1997, 84, 549.
57. The ladder type polymer [12 a] was proposed to have a structure in which the effective conjugation length was large due to a lack of non-planar regions.
58. Najechalski et al. [12 c] reported a proposed a poly((8,8-dihexyl)- fluorene-2,7-diyl) structure.
59. 17 were investigated[12e].
60. a) T. Ahn, M. S. Jang, H.-K. Shim, D.-H. Hwang, T. Zyung, Macromolecules 1999, 32, 3279;
61. b) M. Wagner, O. Nuyken, Macromolecules 2003, 36, 6716;
62. c) I. K. Spiliopoulos, J. A. Mikroyannidis, Macromolecules 2002, 35, 2149;
63. d) J. Ma, S. Li, Y. Jiang, Macromolecules 2002, 35, 1109;
64. e) C. J. Collison, L. J. Rothberg, V. Treemaneekarn, Y. Li, Macromolecules 2001, 34, 2346;
65. f) L. X. Chen, W. J. H. Jager, M. P. Niemczyk, M. R. Wasielewski, J. Phys. Chem. A 1999, 103, 4341;
66. g) L. P. Candeias, F. C. Grozema, G. Padmanaban, S. Ramakrishnan, L. D. A. Siebbeles, J. M. Warman, J. Phys. Chem. B 2003, 107, 1554.
67. a) U.-W. Grummt, T. Pautzsch, E. Birckner, H. Sauerbrey, A. Utterodt, U. Neugebauer, E. Klemm, J. Phys. Org. Chem. 2004, 17, 199;
68. b) D. A. M. Egbe, C. Bader, E. Klemm, L. Ding, F. E. Karasz, U.-W. Grummt, E. Birckner, Macromolecules 2003, 36, 9303.
69. a) S. J. Strickler, R. A. Berg, J. Chem. Phys. 1962, 37, 814;
70. b) J. B. Birks, Photophysics of Aromatic Molecules, Wiley-Interscience, 1970, Ch. 4.
71. A. M. Sarker, L. Ding, P. M. Lahti, F. E. Karasz, Macromolecules 2002, 35, 223.
72. a) T. Fujii, S. Suzuki, S. Komatsu, Chem. Phys. Lett. 1978, 57, 175;
73. b) T. Fujii, S. Suzuki, S. Komatsu, Bull. Chem. Soc. Jpn. 1982, 55, 2576.
74. max (THF) = 387 nm. The small polydispersity documents the efficient cut of molecular weight by semipreparative GPC.
75. G. Klaerner, R. D. Miller, Macromolecules 1998, 31, 2007.
76. H. Mauser, G. Gauglitz, Photokinetics: Theoretical Fundamentals and Applications, Vol. 36, Elsevier, Amsterdam, 1998.
77. a) E. G. Rae, M. Kasha, J. Chem. Phys. 1958, 28, 721;
78. b) A. S. Davydov, M. Kasha, M. Oppenheimer, Theory of Molecular Excitons, McGraw-Hill Book Company, Inc., 1962, pp. 141-156.
79. a) Y. Morel, O. Stephan, C. Andraud, P. L. Baldeck, Synth. Met. 2001, 124, 237;
80. b) C. Martineau, G. Lemercier, C. Andraud, Opt. Mater. 2002, 21, 555.
81. 2 + 2)/3.
82. B. J. Orr, J. F. Ward, Mol. Phys. 1971, 20, 513.
83. 2.
84. B. Strehmel, K. B. Henbest, A. M. Sarker, J. H. Malpert, D. Y. Chen, M. A. J. Rodgers, D. C. Neckers, J. Nanosci. Nanotechnol. 2001, 1, 107.
85. a) A. Gilbert in Synthetic Organic Photochemistry (Ed. W. M. Horspool), Plenum Press, New York, 1984, p. 1;
86. b) A. Pawda, C. Doubleday, A. Mazzu, J. Org. Chem. 1977, 42, 3271.
87. +, because no evidence was found for any end group in the spectra. Further peak assignment for the spectrum in Figure 7 gives evidence for linear structures of 3 with different end groups. In addition, the appearance of oligomers and polymers with 3-11 repeating units can be seen in spectral pattern of the MALDI-TOF spectra for 3. This is the case for the cyclic and the linear structures, respectively. Lower molecular weight oligomers were not detectable because of the signals from the dithranol matrix. Furthermore, the molecular weight distribution shown by MALDI-TOF differs from that of GPC because of discrimination of higher molecular weight oligomers and polymers in MALDI-TOF analyses.
88. a) C. Xu, W. W. Webb, J. Opt. Soc. Am. B 1996, 13, 481;
89. b) C. Xu, J. Guild, W. W. Webb, W. Denk, Opt. Lett. 1995, 20, 2372.
90. A. Utterodt, Ph.D. Thesis, Martin-Luther University Halle-Wittenberg, Germany, 1999.