Novel PPV/mesoporous organosilica composites: Influence of the host chirality on a conjugated polymer guest

Langmuir

Volumn 29, Issue 40, 2013, Pages 12579-12584

  Mehr, S Hessam M ^a   Giese, Michael ^a   Qi, Hao ^a   Shopsowitz, Kevin E ^a   Hamad, Wadood Y ^b   Maclachlan, Mark J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b FPINNOVATIONS   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 ,4 ,6-TRINITROTOLUENE; CHARACTERISTIC FLUORESCENCE; CHIRAL STRUCTURES; ELECTRON-DEFICIENT; FLUORESCENCE QUENCHING; FLUORESCENT MATERIALS; MESOPOROUS ORGANOSILICAS; POLY-P-PHENYLENEVINYLENE;

COMPOSITE FILMS; FLUORESCENCE; PHOTONIC BAND GAP;

SILICA;

EID: 84885405810     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la4024597     Document Type: Article

References (48)

1. McDonald, R. N.; Campbell, T. W. The Wittig reaction as a polymerization method J. Am. Chem. Soc. 1960, 82, 4669-4671
2. Yu, G.; Heeger, A. J. High efficiency photonic devices made with semiconducting polymers Synth. Met. 1997, 85, 1183-1186
3. Heeger, A. J. Semiconducting and metallic polymers: The fourth generation of polymeric materials (Nobel Lectures) Angew. Chem., Int. Ed. 2001, 40, 2591-2611
4. Teichler, A.; Eckart, R.; Friebe, C.; Perelaer, J.; Schubert, U. S. Film formation properties of inkjet printed poly(phenylene-ethylene)-poly(phenylene- vinylene)s Thin Solid Films 2011, 519, 3695-3702
5. Ho, P. K. H.; Thomas, D. S.; Friend, R. H.; Tessler, N. All-polymer optoelectronic devices Science 1999, 285, 233-236
6. Feng, L.; Li, H.; Qu, Y.; Lü, C. Detection of TNT based on conjugated polymer encapsulated in mesoporous silica nanoparticles through FRET Chem. Commun. 2012, 48, 4633-4635
7. Tessler, N.; Denton, G. J.; Friend, R. H. Lasing from conjugated-polymer microcavities Nature 1996, 382, 695-697
8. Puzzo, D. P.; Scotognella, F.; Zavelani-Rossi, M.; Sebastian, M.; Lough, A. J.; Manners, I.; Lanzani, G.; Tubino, R.; Ozin, G. A. Distributed feedback lasing from a composite poly(phenylene vinylene)-nanoparticle one-dimensional photonic crystal Nano Lett. 2009, 9, 4273-4278
9. Furmanchuk, A.; Leszczynski, J.; Tretiak, S.; Kilina, S. V. Morphology and optical response of carbon nanotubes functionalized by conjugated polymers J. Phys. Chem. C 2012, 116, 6831-6840
10. Smith, R. C.; Fischer, W. M.; Gin, D. L. Ordered poly(p -phenyelenvinylene) matrix nanocomposites via lyotropic liquid-crystalline monomers J. Am. Chem. Soc. 1997, 119, 4092-4093
11. Skaff, H.; Sill, K.; Emrick, T. Quantum dots tailored with poly(para -phenylene vinylene) J. Am. Chem. Soc. 2004, 126, 11322-11325
12. Kyotani, M.; Matsushita, S.; Goh, M.; Nagai, T.; Matsui, Y.; Akagi, K. Entanglement-free fibrils of aligned polyacetylene films that produce single nanofibers Nanoscale 2010, 2, 509-514
13. Ozin, G. A.; Chomski, E.; Khushalani, D.; MacLachlan, M. J. Mesochemistry Curr. Opin. Colloid Interface Sci. 1998, 3, 181-193
14. Moller, K.; Bein, T. Inclusion chemistry in periodic mesoporous hosts Chem. Mater. 1998, 10, 2950-2963
15. Pattantyus-Abraham, A. G.; Wolf, M. O. A PPV/MCM-41 composite material Chem. Mater. 2004, 16, 2180-2186
16. Service, R. F. Can chemists assemble a future for molecular electronics? Science 2002, 295, 2398-2399
17. Nguyen, T.-Q.; Wu, J. J.; Doan, V.; Schwartz, B. J.; Tolbert, S. H. Control of energy transfer in oriented conjugated polymer-mesoporous silica composites Science 2000, 288, 652-656
18. Wessling, R. A. The polymerization of xylylene bisdialkyl sulfonium salts J. Polym. Sci., Polym. Symp. 1985, 55-66
19. Lenz, R. W.; Han, C.-C.; Stenger-Smith, J. D.; Karasz, F. E. Preparation of poly(phenylene vinylene) from cycloalkylene sulfonium salt monomers and polymers J. Polym. Sci., Part A 1988, 26, 3241-3249
20. Chen, S. H.; Katsis, D.; Schmidt, A. W.; Masterangelo, J. C.; Tsutsui, T.; Blanton, T. N. Circularly polarized light generated by photoexcitation of luminophores in glassy liquid crystal films Nature 1999, 397, 506-508
21. Cooper, A. I. Conjugated microporous polymers Adv. Mater. 2009, 21, 1291-1295
22. Molenkamp, W. C.; Watanabe, M.; Miyata, H.; Tolbert, S. H. Highly polarized luminescence from optical quality films of a semiconducting polymer aligned within oriented mesoporous silica J. Am. Chem. Soc. 2004, 126, 4476-4477
23. Kelly, T. L.; Yamada, Y.; Schneider, C.; Yano, K.; Wolf, M. O. Enhanced optical properties and opaline self-assembly of PPV encapsulated in mesoporous silica spheres Adv. Funct. Mater. 2009, 19, 3737-3745
24. Matsushita, S.; Akagi, K. Synthesis of conjugated polymers in chiral nematic liquid crystal fields Isr. J. Chem. 2011, 51, 1075-1095
25. Naarrmann, H.; Theophilou, N. New process for the production of metal-like, stable polyacetylene Synth. Met. 1987, 22, 1-8
26. Akagi, K.; Suezaki, M.; Shirakawa, H.; Kyotani, H.; Shimomura, M.; Tannabe, Y. Synthesis of polyacetylene films with high density and high mechanical strength Synth. Met. 1989, 28, D1-D10
27. Cao, Y.; Smith, P.; Heeger, A. J. Mechanical and electrical properties of polyacetylene films oriented by tensile drawing Polymer 1991, 32, 1210-1218
28. Shibahara, S.; Yamane, M.; Ishikawa, K.; Takezoe, H. Direct synthesis of oriented trans -polyacetylene films Macromolecules 1998, 31, 3756-3758
29. Scherman, O. A.; Grubbs, R. H. Polycyclooctatetraene (polyacetylene) produced with a ruthenium olefin metathesis catalyst Synth. Met. 2001, 124, 431-434
30. Scherman, O. A.; Rutenberg, I. M.; Grubbs, R. H. Direct synthesis of soluble, end-functionalized polyenes and polyacetylene block copolymers J. Am. Chem. Soc. 2003, 125, 8515-8522
31. Gu, H.; Zheng, R.; Zhang, X.; Xu, B. Using soft lithography to pattern highly oriented polyacetylene (HOPA) films via solventless polymerization Adv. Mater. 2004, 16, 1356-1359
32. Satrijo, A.; Meskers, S. C. J.; Swager, T. M. Probing a conjugated polymer's transfer of organization-dependent properties from solutions to films J. Am. Chem. Soc. 2006, 128, 9030-9031
33. Peeters, E.; Christiaans, M. P. T.; Janssen, R. A. J.; Schoo, H. F. M.; Dekkers, H. P. J. M.; Meijer, E. W. Circularly polarized electroluminescence from a polymer light-emitting diode J. Am. Chem. Soc. 1997, 119, 9909-9910
34. Akagi, K.; Piao, G.; Kaneko, S.; Sakamaki, K.; Shirakawa, H.; Kyotani, M. Helical polyacetylene synthesized with a chiral nematic reaction field Science 1998, 282, 1683-1686
35. Akagi, K.; Mori, T. Helical polyacetylene-origins and synthesis Chem. Rec. 2008, 8, 395-406
36. Akagi, K.; Guo, S.; Mori, T.; Goh, M.; Piao, G.; Kyotani, M. Synthesis of helical polyacetylene in chiral nematic liquid crystals using crown ether type binaphthyl derivatives as chiral dopants J. Am. Chem. Soc. 2005, 127, 14647-14654
37. Goto, H.; Akagi, K. Optically active conjugated polymers prepared from achiral monomers by polycondensation in a chiral nematic solvent Angew. Chem., Int. Ed. 2005, 44, 4322-4328
38. Watanabe, K.; Osaka, I.; Yorozuya, S.; Akagi, K. Helically π-stacked thiophene-based copolymers with circularly polarized fluorescence: High dissymmetry factors enhanced by self-ordering in chiral nematic liquid crystal phase Chem. Mater. 2012, 24, 1011-1024
39. Shopsowitz, K. E.; Qi, H.; Hamad, W. Y.; MacLachlan, M. J. Free-standing mesoporous silica thin films with tunable chiral nematic structures Nature 2010, 468, 422-425
40. Shopsowitz, K. E.; Hamad, W. Y.; MacLachlan, M. J. Flexible and iridescent chiral nematic mesoporous organosilica films J. Am. Chem. Soc. 2012, 134, 867-870
41. Shopsowitz, K. E.; Hamad, W. Y.; MacLachlan, M. J. Chiral nematic mesoporous carbon derived from nanocrystalline cellulose Angew. Chem., Int. Ed. 2011, 50, 10991-10995
42. Qi, H.; Shopsowitz, K. E.; Hamad, W. Y.; MacLachlan, M. J. Chiral nematic assemblies of silver nanoparticles in mesoporous silica thin films J. Am. Chem. Soc. 2011, 133, 3728-3731
43. Samuel, I. D. W.; Crystall, B.; Rumbles, G.; Burn, P. L.; Holmes, A. B.; Friend, R. H. Time-resolved luminescence measurements in poly(p -phenylenevinylene) Synth. Met. 1993, 54, 281-288
44. Saeva, F. D.; Sharpe, P. E.; Olin, G. R. Cholesteric liquid crystal induced circular dichroism (LCICD). V. Mechanistic aspects of LCICD J. Am. Chem. Soc. 1973, 95, 7656-7659
45. Edgar, C. D.; Gray, D. G. Induced circular dichroism of chiral nematic cellulose films Cellulose 2001, 8, 5-12
46. Kelly, J. A.; Shopsowitz, K. E.; Ahn, J. M.; Hamad, W. Y.; MacLachlan, M. J. Chiral nematic stained glass: Controlling the optical properties of nanocrystalline cellulose-templated materials Langmuir 2012, 28, 17256-17262
47. Pålsson, L.-O.; Vaughan, H. L.; Monkman, A. P. Polarized optical spectroscopy applied to investigate two poly(phenylene-vinylene) polymers with different side chain structures J. Chem. Phys. 2006, 125, 164701-164708
48. Sato, T.; Terao, K.; Teramoto, A.; Fujiki, M. Molecular properties of helical polysilylenes in solution Polymer 2003, 44, 5477-5495