Polymer reaction of poly(p-phenylene-ethynylene) by addition of decaborane: Modulation of luminescence and heat resistance

Polymer Journal

Volumn 42, Issue 5, 2010, Pages 363-367

  Kokado, Kenta ^a   Chujo, Yoshiki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

heat resistance; Addition reaction; Carborane; Luminescence; P conjugated polymer

Indexed keywords

ABSORPTION AND PHOTOLUMINESCENCE; BORON CLUSTERS; CARBON-CARBON TRIPLE BONDS; CARBORANE; CARBORANES; CONJUGATION LENGTH; DECABORANES; FEED RATIOS; P-CONJUGATED POLYMER; POLY(P-PHENYLENE-ETHYNYLENE); POLYMER MAIN CHAIN; POLYMER REACTION;

AROMATIC COMPOUNDS; BORON; BORON COMPOUNDS; HEAT RESISTANCE; LUMINESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; SPECIFIC HEAT; SYNTHESIS (CHEMICAL);

ADDITION REACTIONS;

EID: 77952060238     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2010.13     Document Type: Article

References (47)

1. Skothim, T. A., Elsenbaumer, R. L. & Reynolds, J. Handbook of Conducting Polymers, 2nd edn, Marcel Dekker: New York, (1997).
2. Burroughes, J. H., Bradley, D. D. C., Brown, A. R., Marks, R. N., Mackay, K., Friend, R. H., Burns, P. L. & Holmes, A. B. Light-emitting diodes based on conjugated polymers. Nature 347, 539-541 (1990). (Pubitemid 120015057)
3. Gustafsson, G., Cao, Y., Treacy, G. M., Klavetter, F., Colaneri, N. & Heeger, A. J. Flexible light-emitting diodes made from soluble conducting polymer. Nature 357, 477-479 (1992). (Pubitemid 23571387)
4. Gross, M., Muller, D. C., Nothofer, H.-G., Scherf, U., Neher, D., Brauchle, C. & Merrholz, K. Improving the performance of doped p-conjugated polymers for use in organic light-emitting diodes. Nature 405, 661-665 (2000). (Pubitemid 30428647)
5. Sirringhaus, H., Tessler, N. & Friend, R. H. Integrated optoelectronic devices based on conjugated polymers. Science 280, 1741-1744 (1998). (Pubitemid 28283495)
6. Babel, A. & Jenekhe, S. A. High electron mobility in ladder polymer field-effect transistors. J. Am. Chem. Soc. 125, 13656-13657 (2003). (Pubitemid 37386028)
7. McQuade, D. T., Pullen, A. E. & Swager, T. M. Conjugated polymer-based chemical sensors. Chem. Rev. 100, 2537-2574 (2000).
8. Thomas##III, S. W., Joly, G. D. & Swager, T. M. Chemical sensors based on amplifying fluorescent conjugated polymers. Chem. Rev. 107, 1339-1386 (2007).
9. Bunz, U. H. F. Poly (aryleneethynylene): syntheses, properties, structures, and applications. Chem. Rev. 100, 1605-1644 (2000).
10. Bunz, U. H. F. Synthesis and structure of PAEs. Adv. Polym. Sci. 177, 1-52 (2005).
11. Clark, A. P.-Z., Shen, K.-F., Rubin, Y. F. & Tolbert, S. H. An amphiphilic poly (phenylene ethynylene) as the structure-directing agent for periodic nanoscale silica composite materials. Nano Lett. 5, 1647-1652 (2005).
12. Winter, A., Friebe, C., Hager, M. D. & Schubert, U. S. Advancing the solid state properties of metallo-supramolecular materials: poly (å-caprolactone) modified p-conjugated Bis (terpyridine) s and their Zn (II) based metallo-polymers. Macromol. Rapid Commun. 29, 1679-1686 (2008).
13. Wung, C. J., Pang, Y., Prasad, P. N. & Karasz, F. E. Poly (p-phenylene vinylene)-silica composite: a novel sol-gel processed non-linear optical material for optical waveguides. Polymer 32, 605-608 (1991).
14. Kubo, M., Takimoto, C., Minami, Y., Uno, T. & Ito, T. Incorporation of p-conjugated polymer into silica: preparation of poly[2-methoxy-5-(2- ethylhexyloxy)-1,4-phenylenevinylene]/silica and poly (3-hexylthiophene)/silica composites. Macromolecules 38, 7314-7320 (2005). (Pubitemid 41305030)
15. Kokado, K. & Chujo, Y. Poly (p-phenyleneethynylene)-silica gel hybrids without any compatibilizer. Chem. Lett. 37, 732-733 (2008).
16. Kokado, K. & Chujo, Y. Homogeneous anionic ppe hybrids with silica gel. J. Polym. Sci., Part A: Polym. Chem. 46, 3749-3755 (2008).
17. Ogoshi, T. & Chujo, Y. Synthesis of amorphous and nano-structured cationic polyacetylene/silica hybrids by using ionic interaction. Macromolecules 38, 9110-9116 (2005). (Pubitemid 41599885)
18. Lu, M., Xie, B., Kang, J., Chen, F.-C., Yang, Y. & Peng, Z. Synthesis of main-chain polyoxometalate-containing hybrid polymers and their applications in photovoltaic cells. Chem. Mater. 17, 402-408 (2005). (Pubitemid 40139715)
19. Xu, B., Lu, M., Kang, J., Wang, D., Brown, J. & Peng, Z. Synthesis and optical properties of conjugated polymers containing polyoxometalate clusters as side-chain pendants. Chem. Mater. 17, 2841-2851 (2005). (Pubitemid 40850252)
20. Miyake, J. & Chujo, Y. Thermally stabilized blue luminescent poly (p-phenylene) s covered with polyhedral oligomeric silsesquioxanes. Macromol. Rapid Commun. 29, 86-92 2008.
21. Miyake, J. & Chujo, Y. Persistent and emission color tunable poly (phenylene-ethynylene) s covered with polyhedral oligomeric silsesquioxanes. J. Polym. Sci., Part A: Polym. Chem. 46, 8112-8116 (2008).
22. Miyake, J. & Chujo, Y. A Hybrid-Type, chiral p-conjugated polymer wrapped with polyhedral oligomeric silsesquioxanes. J. Polym. Sci., Part A: Polym. Chem. 46, 6035-6040 (2008).
23. Miyake, J., Sawamura, T., Kokado, K. & Chujo, Y. Amphiphilic hybrid p-conjugated polymers containing polyhedral oligomeric silsesquioxanes. Macromol. Rapid Commun. 30, 1559-1563 (2009).
24. Simon, Y. C., Peterson, J. J., Mangold, C., Carter, K. R. & Coughlin, E. B. Synthesis of polyfluorenes with pendant silylcarboranes. Macromolecules 42, 512-516 (2009).
25. Kokado, K. & Chujo, Y. Emission via aggregation of alternating polymers with o-carborane and p-phenylene-ethynylene sequences. Macromolecules 42, 1418-1420 (2009).
26. Kokado, K., Tokoro, Y. & Chujo, Y. Luminescent m-carborane-based p-conjugated polymer. Macromolecules 42, 2925-2930 (2009).
27. Kokado, K., Tokoro, Y. & Chujo, Y. Luminescent and axially chiral p-conjugated polymers linked by carboranes in the main chain. Macromolecules 42, 9238-9242 (2009).
28. Luo, J., Xie, Z., Lam, J. W. Y., Cheng, L., Tang, B. Z., Chen, H., Qiu, C., Kwok, H. S., Zhan, X., Liu, Y. & Zhu, D. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun. 37, 1740-1741 (2001). (Pubitemid 32906757)
29. Hong, Y., Lam, J. W. Y. & Tang, B. Z. Aggregation-induced emission: phenomenon mechanism and applications. Chem. Commun. 45, 4332-4353 (2009).
30. Liu, J., Lam, J. W. Y. & Tang, B. Z. Acetylenic Polymers: Syntheses, Structures, and Functions. Chem. Rev. 109, 5799-5867 (2009).
31. Peterson, J. J., Simon, Y. C., Coughlin, E. B. & Carter, K. R. Polyfluorene with p-carborane in the backbone. Chem. Commun. 45, 4950-4952 (2009).
32. Peterson, J. J., Werre, M., Simon, Y. C., Coughlin, E. B. & Carter, K. R. Carborane-containing polyfluorene: o-carborane in the main chain. Macromolecules 42, 8594-8598 (2009).
33. Michinobu, T. Click-type reaction of aromatic polyamines for improvement of thermal and optoelectronic properties. J. Am. Chem. Soc. 130, 14074-14075 (2008).
34. Michinobu, T., Kumazawa, H., Noguchi, K. & Shigehara, K. One-step synthesis of donoracceptor type conjugated polymers from ferrocene-containing poly (aryleneethynylene) s. Macromolecules 42, 5903-5905 (2009).
35. Hayashi, S., Inagi, S. & Fuchigami, T. Synthesis of 9-substituted fluorene copolymers via chemical and electrochemical polymer reaction and their optoelectronic properties. Macromolecules 42, 3755-3760 (2009).
36. Inagi, S., Hayashi, S., Hosaka, K. & Fuchigami, T. Facile functionalization of a thiophenefluorene alternating copolymer via electrochemical polymer reaction. Macromolecules 42, 3881-3883 (2009).
37. Weder, C. & Wrighton, M. S. Efficient solid-state photoluminescence in new poly (2, 5-dialkoxy-p-phenyleneethynylene) s. Macromolecules 29, 5157-5165 (1996). (Pubitemid 126548711)
38. 9] and 1, 21, 7 isomerized products. Organometallics 24, 2964-2970 (2005).
39. Fox, M. A., Howard, J. A. K., MacBride, H., Mackinnon, A. & Wade, K. Big macrocyclic assemblies of carboranes (big MACs): synthesis and crystal structure of a macrocyclic assembly of four carboranes containing alternate ortho-and meta-carborane icosahedra linked by para-phenylene units. J. Organomet. Chem. 680, 155-164 (2003).
40. 11. Organometallics 6, 80-88 (1987).
41. Palmans, A. R. A., Smith, P. & Weder, C. Polarizing energy transfer in photoluminescent conjugated polymers with covalently attached sensitizers. Macromolecules 32, 4677-4685 (1999).
42. 3Sn-moiety as a recyclable carrier to introduce the ethynyl unit into the chain. J. Polym. Sci., Part A: Polym. Chem. 38, 2603-2621 (2000).
43. Liu, X., Zhu, M., Chen, S., Yuan, M., Guo, Y., Song, Y., Liu, H. & Li, Y. Organic-inorganic nanohybrids via directly grafting gold nanoparticles onto conjugated copolymers through the diels-alder reaction. Langmuir 24, 11967-11974 (2008).
44. Lu, S.-Y. & Hamerton, I. Recent developments in the chemistry of halogen-free flame retardant polymers. Prog. Polym. Sci. 27, 1661-1712 (2002). (Pubitemid 34811634)
45. González-Campo, A., Boury, B., Teixidor, F. & Núñez, R. Carboranyl units bringing unusual thermal and structural properties to hybrid materials prepared by solgel process. Chem. Mater. 18, 4344-4353 (2006).
46. Ichitani, M., Yonezawa, K., Okada, K. & Sugimoto, T. Silyl-carborane hybridized diethynylbenzene-silylene polymers. Polym. J. 31, 908-912 (1999). (Pubitemid 30530674)
47. 29Si NMR spectroscopy. Chem. Mater. 15, 355-362 (2003).