Role of boron in the polymer chemistry and photophysical properties of difluoroboron-dibenzoylmethane polylactide

Macromolecules

Volumn 42, Issue 22, 2009, Pages 8627-8633

  Zhang, Guoqing ^a   Evans, Ruffin E ^a   Campbell, Kirsti A ^a   Fraser, Cassandra L ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONATION; CELL BIOLOGY; CORE STRUCTURE; DIBENZOYLMETHANE; DIKETONES; DUAL EMISSIONS; FREE MODEL; FUNCTIONALIZED; LUMINESCENT PROPERTY; MATRIX; MULTI-PHOTON MICROSCOPY; PHOTOPHYSICAL PROPERTIES; POLY LACTIDE; POLYLACTIC ACIDS; POLYLACTIDES; POLYMER CHEMISTRY; POLYMER CONJUGATE; POLYMERIC MATERIAL; POLYMERIZATION KINETICS; PROTECTING GROUP; ROOM TEMPERATURE PHOSPHORESCENCE; TUMOR HYPOXIA;

BORON; BORON COMPOUNDS; CHROMOPHORES; CYTOLOGY; FLUORESCENCE; FLUORINE CONTAINING POLYMERS; INTERNET PROTOCOLS; KETONES; LACTIC ACID; ORGANIC ACIDS; RAPID THERMAL ANNEALING; RING OPENING POLYMERIZATION; TIN;

POLYMERS;

EID: 71549160850     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9019043     Document Type: Article

References (67)

1. (a) Vigato, P. A.; Peruzzo, V.; Tamburini, S. Coord. Chem. Rev. 2009, 253, 1099-1201.
2. (b) Darr, J. A.; Poliakoff, M. Chem. Rev. 1999, 99, 495-542.
3. (c) Koepf-Maier, P.; Koepf, H. Chem. Rev. 1987, 87, 1137-1152.
4. (a) Jackson, K. M.; Frazier, M. C.; Harris, W. B. Anticancer Res. 2007, 27, 1483-1488.
5. (b) Lin, C.-C.; Tsai, Y.-L.; Huang, M.-T.; Lu, Y.-P.; Ho, C.-T.; Tseng, S.-F.; Teng, S.-C. Carcinogenesis 2006, 27, 131-136.
6. (c) Singletary, K.; MacDonald, C.; Iovinelli, M.; Fischer, C.; Wallig, M. Carcinogenesis 1998, 19, 1036-1043.
7. (a) Huong, S. P.; Rocher, E.; Fourneron, J.-D.; Charles, L.; Monnier, V.; Bun, H.; Andrieu, V. J. Photochem. Photobiol. A: Chem. 2008, 196, 106-112.
8. (b) Scalia, S.; Villani, S.; Scatturin, A.; Vandelli, M. A.; Forni, F. Int. J. Pharm. 1998, 175, 205-213.
9. Kido, J.; Okamoto, Y. Chem. Rev. 2002, 102, 2357-2368.
10. Kuriki, K.; Koike, Y.; Okamoto, Y. Chem. Rev. 2002, 102, 2347-2356.
11. Ling, Q. D.; Kang, E. T.; Neoh, K. G.; Huang, W. Macromolecules 2003, 36, 6995-7003.
12. Bender, J. L.; Corbin, P. S.; Fraser, C. L.; Metcalf, D. H.; Richardson, F. S.; Thomas, E. L.; Urbas, A. M. J. Am. Chem. Soc. 2002, 124, 8526-8527.
13. Manners, I. Science 2001, 294, 1664-1666.
14. Bender, J. L.; Shen, Q.-D.; Fraser, C. L. Tetrahedron 2004, 60, 7277-7285.
15. McAlvin, J. E.; Scott, S. B.; Fraser, C. L. Macromolecules 2000, 33, 6953-6964.
16. Gorczynski, J. L.; Chen, J.; Fraser, C. L. J. Am. Chem. Soc. 2005, 127, 14956-14957.
17. Morgan, G. T.; Tunstall, R. B. J. Chem. Soc. 1924, 125, 1963-1967.
18. Brown, N. M. D.; Bladon, P. J. Chem. Soc. A 1969, 526-532.
19. Chow, Y. L.; Ouyang, X. Can. J. Chem. 1991, 69, 423-431.
20. Chow, Y. L.; Heng, X. Can. J. Chem. 1991, 69, 1575-1583.
21. Chow, Y. L.; Wang, S.; Cheng, X. Can. J. Chem. 1993, 71, 846-854.
22. Chow, Y. L.; Wang, S.; Johansson, C. I.; Liu, Z. J. Am. Chem. Soc. 1996, 118, 11725-11732.
23. (a) Mirochnik, A.; Fedorenko, E.; Kuryavyi, V.; Bukvetskii, B.; Karasev, V. J. Fluoresc. 2006, 16, 279-286.
24. (b) Mirochnik, A.; Fedorenko, E.; Gizzatulina, D.; Karasev, V. Russ. J. Phys. Chem. A 2007, 81, 1880-1883.
25. Cogné-Laage, E.; Allemand, J.-F.; Ruel, O.; Baudin, J.-B.; Croquette, V.; Blanchard-Desce, M.; Jullien, L. Chem.-Eur. J. 2004, 10, 1445-1455.
26. Nagata, Y.; Otaka, H.; Chujo, Y. Macromolecules 2008, 41, 737-740.
27. Nagai, A.; Kodado, K.; Nagata, Y.; Chujo, Y. Macromolecules 2008, 41, 8295-8298.
28. Domercq, B.; Grasso, C.; Maldonado, J.-L.; Halik, M.; Barlow, S.; Marder, R.; Kippelen, B. J. Phys. Chem. B 2004, 108, 8647-8651.
29. Albota, M.; Beljonne, D.; Brédas, J.-L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord-Maughon, D.; Perry, J. W.; Rockel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653-1656.
30. Halik, M.; Wenseleers, W.; Grasso, C.; Stellacci, F.; Zojer, E.; Barlow, S.; Brédas, J.-L.; Perry, J. W.; Marder, S. R. Chem. Commun. 2003, 1490-1491.
31. Pfister, A.; Zhang, G.; Zareno, J.; Horwitz, A. F.; Fraser, C. L. ACS Nano 2008, 2, 1252-1258.
32. Contreras, J.; Xie, J.; Pei, H.; Chen, Y. J.; Zhang, G.; Fraser, C. L.; Hamm-Alvarez, S. F., submitted.
33. (a) Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891-4932.
34. (b) Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem., Int. Ed. 2008, 47, 1184-1201.
35. Ozdemir, T.; Atilgan, S.; Kutuk, I.; Yildirim, L. T.; Tulek, A.; Bayindir, M.; Akkaya, E. U. Org. Lett. 2009, 11, 2105-2107.
36. Mirochnik, A. G.; Gukhman, E. V.; Zhihareva, P. A.; Karasev, V. E. Spectrosc. Lett. 2002, 35, 309-315.
37. Chow, Y. L.; Cheng, X.; Johansson, C. I. J. Photochem. Photobiol. A: Chem. 1991, 57, 247-255.
38. Zhang, G.; Kooi, S. E.; Demas, J. N.; Fraser, C. L. Adv. Mater. 2008, 20, 2099-2104.
39. Zhang, G.; Chen, J.; Payne, S. J.; Kooi, S. E.; Demas, J. N.; Fraser, C. L. J. Am. Chem. Soc. 2007, 129, 8942-8943.
40. (a) Galletta, M.; Campagna, S.; Quesada, M.; Ulrich, G.; Ziessel, R. Chem. Commun. 2005, 33, 4222-4224.
41. (b) Nastasi, F.; Puntoriero, F.; Campagna, S.; Diring, S.; Ziessel, R. Phys. Chem. Chem. Phys. 2008, 10, 3982-3986.
42. Zhang, G.; Palmer, G. M.; Dewhirst, M. W.; Fraser, C. L. Nat. Mater. 2009, 5, 747-751.
43. Fang, W.-H. Acc. Chem. Res. 2008, 41, 452-457.
44. (a) Lamola, A. A. J. Chem. Phys. 1967, 47, 4810-4816.
45. (b) Koyanagi, M.; Zwarich, R. J.; Goodman, L. J. Chem. Phys. 1972, 56, 3044-3060.
46. Rubin, M. B.; Gleiter, R. Chem. Rev. 2000, 100, 1121-1164 (section VIII).
47. (a) Almgren, M. Photochem. Photobiol. 1969, 9, 1-6.
48. (b) Speiser, S.; Hassoon, S.; Rubin, M. B. J. Phys. Chem. 1986, 90, 5085-5089.
49. Gacoin, P. J. Chem. Phys. 1972, 57, 1418-1425.
50. (a) Baran, J.; Duda, A.; Kowalski, A.; Szymanski, R.; Penczek, S. Macromol. Rapid Commun. 1997, 18, 325-333.
51. (b) Save, M.; Schappacher, M.; Soum, A. Macromol. Chem. Phys. 2002, 203, 889-899.
52. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991-1024 (section II.C.2, eq 16).
53. Dawson, W. R.; Windsor, M. W. J. Phys. Chem. 1968, 72, 32513260.
54. Zhang, G.; Sabat, M.; Fraser, C. L. Unpublished results.
55. Saad, G. R.; Naoum, M. M.; Rizk, H. A. Can. J. Chem. 1989, 67, 284-288.
56. Morita, H.; Nakanishi, H. Bull. Chem. Soc. Jpn. 1981, 54, 378-386.
57. Fabian, J.; Hartmann, H. J. Phys. Org. Chem. 2004, 17, 359-369.
58. Rumi, M.; Ehrlich, J. E.; Heikal, A. A.; Perry, J. W.; Barlow, S.; Hu, Z.; McCord-Maughon, D.; Röckel, H.; Thayumanavan, S.; Marder, S. R.; Beljonne, D.; Brédas, J.-L. J. Am. Chem. Soc. 2000, 122, 9500-9510.
59. Jhaveri, S.; Ober, C. K.; Zipfel, W. R.; Zhang, G.; Fraser, C. L. Unpublished results.
60. Gorczynski, J. L. Ph.D. Thesis, University of Virginia, 2005.
61. Mackay, S. C.; Preston, P. N.; Will, S. G.; Morley, J. O. J. Chem. Soc., Chem. Commun. 1982, 7, 395-396.
62. Fister, J. C.III; Harris, J. M.; Rank, D.; Wacholtz, W. J. Chem. Educ. 1997, 74, 1208-1212.
63. Carraway, E. R.; Demas, J. N.; DeGraff, B. A.; Bacon, J. R. Anal. Chem. 2002, 63, 337-342.
64. Lamola, A. A.; Sharp, L. J. J. Phys. Chem. 1966, 70, 2634-2638.
65. Williams, D. E. Acta Crystallogr. 1966, 21, 340-349.
66. Mirochnik, A. G.; Bukvetskii, B. V.; Gukhman, E. V.; Zhikhareva, P. A.; Karasev, V. E. Russ. Chem. Bull. 2001, 50, 1612-1615.
67. Morantz, D. J.; Wright, A. J. C. J. Chem. Phys. 1971, 54, 692-697.