Synthesis of organoboron quinoline-8-thiolate and quinoline-8-selenolate complexes and their incorporation into the π-conjugated polymer main-chain

Macromolecules

Volumn 42, Issue 8, 2009, Pages 2988-2993

  Tokoro, Yuichiro ^a   Nagai, Atsushi ^a   Kokado, Kenta ^a   Chujo, Yoshiki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC NUMBERS; BORON ATOM; COMPLEX STRUCTURE; CONJUGATED LINKERS; COUPLING REACTION; DIETHYNYLBENZENE; EFFICIENT ENERGY TRANSFER; ELECTRON-DONATING; EMISSION SHIFTS; HIGH REFRACTIVE INDEX; MAIN CHAINS; MODEL COMPOUND; NMR SPECTROSCOPY; ORGANOBORON; ORGANOBORON POLYMERS; PHOTOLUMINESCENCE PROPERTIES; POLY(P-PHENYLENE-ETHYNYLENE); QUINOLATE; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; THIOLATE; UV-VIS ABSORPTIONS;

ABSORPTION SPECTROSCOPY; ATOMS; BORON; BORON COMPOUNDS; EMISSION SPECTROSCOPY; ENERGY TRANSFER; MODEL STRUCTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC POLYMERS; PHOTOLUMINESCENCE; POLYMERS; REFRACTIVE INDEX; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CONJUGATED POLYMERS;

EID: 66549129333     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma900008m     Document Type: Article

References (32)

1. (a) Hadziioannou, G., van Hutten, P. F., Eds., Semiconducting polymers: Chemistry, Physics and Engineering, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2006.
2. (b) Skotheim, T. J., Elsenbaumer, R. L. Reynolds, J. R., Eds. Handbook of Conducting Polymers, 2nd ed.; Dekker: New York, 1998.
3. (c) Martin, R. E.; Diederich, F. Angew. Chem. 1999, 111, 1440.
4. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. 1998, 110, 416.
5. Hide, F.; Diaz-Garcia, M. A.; Schwartz, B. J.; Heeger, A. J. Acc. Chem. Res. 1997, 30, 430.
6. Screen, T. E. O.; Lawton, K. B.; Wilson, G. S.; Dolney, N.; Ispasoiu, R.; Goodson, T., III; Martin, S. J.; Bradley, D. D. C.; Anderson, H. L. J. Mater. Chem 2001, 11, 312.
7. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
8. (a) Bao, Z.; Rogers, J. A.; Katz, H. E. J. Mater. Chem. 1999, 9, 1895.
9. (b) Calvert, P. Chem. Mater. 2001, 13, 3299.
10. Haugland, R. P. In The Handbook-A Guide to Fluorescent Probes and Labeling Technologies, 10th ed.; Spence, M. T. Z., Ed.; Molecular Probes: Eugene. OR, 2005; Chapter 1, Section 1.4.
11. Gorman, A.; Killoran, J.; O'Shea, C.; Kenna, T.; Gallagher, W. M.; O'Shea, D. F. J. Am. Chem. Soc. 2004, 126, 10619.
12. (a) Garcla-Moreno, I.; Costela, A.; Campo, L.; Sastre, R.; Amat-Guerri, F.; Liras, M.; Lopez Arbeloa, I. J. Phys. Chem. A 2004, 108, 3315.
13. (b) Pavlopoulos, T. G.; Boyer, J. H.; Sathyamoorthi, G. Appl. Opt. 1998, 37, 7797.
14. (a) Nagata, Y.; Chujo, Y. Macromolecules 2007, 40, 6.
15. (b) Nagata, Y.; Chujo, Y. Macromolecules 2008, 41, 2809.
16. (a) Cheng, Y. M.; Yeh, Y. S.; Ho, M. L.; Chou, P. T.; Chen, P. S.; Chi, Y. Inorg. Chem. 2005, 44, 4594.
17. (b) Shi, Y.-W.; Shi, M.-M.; Huang, J.-C.; Chen, H.-Z.; Wang, M.; Liu, X.-D.; Ma, Y.-G.; Xu, H.; Yang, B. Chem. Commun. 2006, 1941.
18. (a) Chen, C. H.; Shi, J. C. Coord. Chem. Rev. 1998, 171, 161.
19. (b) Ballardini, R.; Varani, G.; Indelli, M. T.; Scandola, F. Inorg. Chem. 1986, 25, 3858.
20. Shavaleev, N. M.; Adams, H.; Best, J.; Edge, R.; Navaratnam, S.; Weinstein, J. A. Inorg. Chem. 2006, 45, 9410.
21. Higashi, T. ABSCOR. Program for Absorption Correction; Rigaku Corporation: Tokyo, Japan, 1995.
22. Sheldrick, G. M. SHELX-97. Programs for Crystal Structure Analysis.; University of Gottingen: Gottingen, Germany, 1997.
23. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giaco- vazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
24. Wakita, K. Yadokari-XG. Program for Crystal Structure Analysis; 2000.
25. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
26. Ashaks, J.; Bankovsky, Y.; Zaruma, D.; Shestakova, I.; Domracheva, I.; Nesterova, A.; Lukevics, E. Chem. Heterocycl. Compd. 2004, 40, 776.
27. Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886.
28. Nagai, A.; Miyake, J.; Kokado, K.; Nagata, Y.; Chujo, Y. J. Am. Chem. Soc. 2008, 130, 15276.
29. Wu, Q.; Esteghamatian, M.; Hu, N.-X.; Popovic, Z.; Enright, G.; Tao, Y.; D'Iorio, M.; Wang, S. Chem. Mater. 2000, 12, 79.
30. Egbe, D. A. M.; Roll, C. P.; Brickner, E.; Grummt, U.-W.; Stockmann, R.; Klemm, E. Macromolecules 2002, 35, 3825.
31. Okubo, T.; Kohmoto, S.; Yamamoto, M. J. Polym. Sci., Part A: Polym. Chem. 1998, 68, 1791.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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.; 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 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.