Two-dimensional conjugated polymer assemblies: Interchain spacing for control of photophysics [5]

Journal of the American Chemical Society

Volumn 122, Issue 24, 2000, Pages 5885-5886

  McQuade, D Tyler ^a   Kim, Jinsang ^a   Swager, Timothy M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; POLYMER;

CHEMICAL STRUCTURE; CONJUGATION; FILM; LETTER; MOLECULAR INTERACTION; OPTICAL ROTATION; SYNTHESIS;

EID: 0034697640     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000553+     Document Type: Letter

References (36)

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21. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer- Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
22. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer- Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
23. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer- Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
24. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer- Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
25. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer-Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
26. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer- Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
27. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer- Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
28. For a review of poly(aryleneethynylene)s see: Bunz, U. H. F Chem Rev. 2000, 100, 1605-1644. Other poly(aryleneethynylene) papers of note: (a) Levitsky, I. A.; Kim, J.; Swager T. M. J. Am. Chem. Soc. 1999, 121, 1466. (b) Sato, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658. (c) Samori, P.; Francke, V.; Müllen, K.; Rabe, J. P. Chem. Eur. J. 1999, 5, 2312. (d) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer- Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655. (f) Weder, C.; Wrighton, M. S. Macromolecules 1996, 29, 5157. (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1996, 29, 5157. (h) Swager, T. M.; Gil, C. J.; Wrighton, M. S. J. Phys. Chem. 1995, 99, 4886-4893.
29. Recently, Miteva et al. (Miteva, T.; Palmer, L.; Kloppenburg, L.; Neher, D.; Bunz, U. H. F. Macromolecules 2000, 33, 652-654.) have postulated, based on their work with liquid crystalline PPEs, that the ground state aggregation peak observed is due solely to planarization of the aryl rings. We feel that both aggregation and planarization contribute significantly to the red-shifted band. The Bunz group also reported (see ref 10e) that induced aggregation of a PPE via addition of a nonsolvent causes planarization; we suggest that the planarization caused by the addition of the methanol is small compared to the effect of chain-chain aggregation. Our group has recently reported (Kim, J.; McQuade, D. T.; Swager, T. M. Polym. Prepr. 2000, 41, 32-33) the detection of potassium ions via polymer-polymer aggregation.
30. Recently, Miteva et al. (Miteva, T.; Palmer, L.; Kloppenburg, L.; Neher, D.; Bunz, U. H. F. Macromolecules 2000, 33, 652-654.) have postulated, based on their work with liquid crystalline PPEs, that the ground state aggregation peak observed is due solely to planarization of the aryl rings. We feel that both aggregation and planarization contribute significantly to the red-shifted band. The Bunz group also reported (see ref 10e) that induced aggregation of a PPE via addition of a nonsolvent causes planarization; we suggest that the planarization caused by the addition of the methanol is small compared to the effect of chain-chain aggregation. Our group has recently reported (Kim, J.; McQuade, D. T.; Swager, T. M. Polym. Prepr. 2000, 41, 32-33) the detection of potassium ions via polymer-polymer aggregation.
31. Kim, J.; McHugh, S. K.; Swager, T. M. Macromolecules 1999, 32, 1500.
32. A Langmuir-Schaefer film is deposited onto a slide by dipping the slide onto the monolayer surface parallel to the air-water interface. Langmuir, I.; Schaefer, V. J. J. Am. Chem. Soc. 1938, 60, 1351. The monolayers of polymer 2 and 3 are too stiff to transfer via the Langmuir-Blodgett method.
33. n = 138 300, PDI = 3.1.
34. For experimental details see: Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
35. Osahemi, J. A.; Jenekhe, S. A. J. Am. Chem. Soc. 1995, 117, 7389.
36. Very little change is observed in the UV-vis or PL after 3 days of thermal annealing at 100°C.