Self-assembly of poly{1,4-phenylene-[9,9-bis(4-phenoxy-butylsulfonate)] fluorene-2,7-diyl} with oppositely charged phenylenevinylene oligoelectrolytes

Journal of Physical Chemistry B

Volumn 118, Issue 2, 2014, Pages 613-623

  Costa, Telma ^a,b   Marques, Ana T ^a,c   Seixas De Melo, J Sérgio ^a   Thomas, Alexander W ^b   Garner, Logan E ^b   Scherf, Ullrich ^c   Bazan, Guillermo C ^b   Burrows, Hugh D ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS MICELLAR SOLUTIONS; CONJUGATED POLYELECTROLYTES; CORE SHELL STRUCTURE; DEGREE OF POLYMERIZATION; PHENYLENEVINYLENE OLIGOMERS; SOLVENT ENVIRONMENTS; SURFACTANT SOLUTION; TIME-RESOLVED FLUORESCENCE;

AROMATIC COMPOUNDS; ENERGY TRANSFER; ETHERS; MIXTURES; POLYOLS;

SELF ASSEMBLY;

EID: 84892691123     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp409577y     Document Type: Article

References (56)

1. Huang, F.; Wu, H.; Wang, D.; Yang, W.; Cao, Y. Novel Electroluminescent Conjugated Polyelectrolytes Based on Polyfluorene Chem. Mater. 2004, 16, 708-711
2. Pu, K.-Y.; Cai, L.; Liu, B. Design and Synthesis of Charge-Transfer-Based Conjugated Polyelectrolytes as Multicolor Light-Up Probes Macromolecules 2009, 42, 5933-5940
3. Liu, B.; Bazan, G. C. Conjugated Polyelectrolytes-Fundamentals and Applications; Wiley-VCH Verlag & o. KGaA: Weinheim, Germany, 2013.
4. Chen, L.; McBranch, D. W.; Wang, H.-L.; Helgeson, R.; Whitten, F. W. D. G. Highly Sensitive Biological and Chemical Sensors Based on Reversible Fluorescence Quenching in a Conjugated Polymer Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12287-12292
5. Liu, B.; Bazan, G. C. Interpolyelectrolyte Complexes of Conjugated Copolymers and DNA: Platforms for Multicolor Biosensors J. Am. Chem. Soc. 2004, 126, 1942-1943
6. Lv, F.; Feng, X.; Tang, H.; Liu, L.; Yang, Q.; Wang, S. Development of Film Sensors Based on Conjugated Polymers for Copper (II) Ion Detection Adv. Funct. Mater. 2011, 21, 845-850
7. Li, Z.; Lou, Z. L. X.; Qin, J. A New Approach to Fluorescence "Turn-On" Sensing of α-Amino Acids Appl. Mater. Interfaces 2009, 1, 232-234
8. Miranda, O. R.; You, C.-C.; Phillips, R.; Kim, I.-B.; Ghosh, P. S.; Bunz, U. H. F.; Rotello, V. M. Array-Based Sensing of Proteins Using Conjugated Polymers J. Am. Chem. Soc. 2007, 129, 9856-9857
9. Feng, F.; Lee, S. H.; Cho, S. W.; Kömürlü, S.; McCarley, T. D.; Roitberg, A.; Kleiman, V. D.; Schanze, K. S. Conjugated Polyelectrolyte Dendrimers: Aggregation, Photophysics, and Amplified Quenching Langmuir 2012, 28, 16679-16691
10. Feng, F.; Liu, L.; Yang, Q.; Wang, S. Water-Soluble Conjugated Polymers for Fluorescent-Enzyme Assays Macromol. Rapid Commun. 2010, 31, 1405-1421
11. Fang, J.; Wallikewitz, B. H.; Gao, F.; Tu, G.; Müller, C.; Pace, G.; Friend, R. H.; Fang, W. T. S. Conjugated Zwitterionic Polyelectrolyte as the Charge Injection Layer for High-Performance Polymer Light-Emitting Diodes J. Am. Chem. Soc. 2011, 133, 683-685
12. Hoven, C. V.; Wang, H.; Elbing, M.; Garner, L.; Winkelhaus, D.; Bazan, G. C. Chemically Fixed p-n Heterojunctions for Polymer Electronics by means of Covalent B-F Bond Formation Nat. Mater. 2010, 9, 249-252
13. Jiang, H.; Taranekar, P.; Reynolds, J. R.; Schanze, K. S. Conjugated Polyelectrolytes: Synthesis, Photophysics, and Applications Angew. Chem., Int. Ed. 2009, 48, 4300-4316
14. Scherf, U. Counterion Pinning in Conjugated Polyelectrolytes for Applications in Organic Electronics Angew. Chem., Int. Ed. 2011, 50, 5016-5017
15. Seo, J. H.; Namdas, E. B.; Gutacker, A.; Heeger, A. J.; Bazan, G. C. Conjugated Polyelectrolytes for Organic Light Emitting Transistors Appl. Phys. Lett. 2010, 97, 043303-3
16. Z., C.; Dang, X. D.; A., G.; Garcia, A.; Li, H.; Xu, Y.; Ying, L.; Nguyen, T.-Q.; Bazan, G. C. Reconstruction of Conjugated Oligoelectrolyte Electron Injection Layers J. Am. Chem. Soc. 2010, 132, 12160-12162
17. Evans, R. C.; Macedo, A. G.; Pradhan, S.; Scherf, U.; Carlos, L. D.; Burrows, H. D. Fluorene Based Conjugated Polyelectrolyte/Silica Nanocomposites: Charge Mediated Phase Aggregation at the Organic-Inorganic Interface Adv. Mater. 2010, 22, 3022-3027
18. Pu, K.-Y.; Li, K.; Zhang, X.; Liu, B. Conjugated Oligoelectrolyte Harnessed Polyhedral Oligomeric Silsesquioxane as Light-Up Hybrid Nanodot for Two-Photon Fluorescence Imaging of Cellular Nucleus Adv. Mater. 2010, 22, 4186-4198
19. Heeley, M. E. H.; Gallaher, J. K.; Nguyen, T.-L.; Woob, H. Y.; Hodgkiss, J. M. Surfactant Controlled Aggregation of Conjugated Polyelectrolytes Chem. Commun. 2013, 49, 4235-4237
20. Dutta, K.; Kundu, P. P. Interaction between oxidized polyaniline and oppositely charged amphiphilic assemblies in an aqueous/organic biphasic system J. Colloid Interface Sci. 2013, 407, 516-523
21. Clark, A. P.-Z.; Shi, C.; Ng, B. C.; Wilking, J. N.; Ayzner, A. L.; Stieg, A. Z.; Schwartz, B. J.; Mason, T. G.; Rubin, Y.; Tolbert, S. H. Self-Assembling Semiconducting Polymers-Rods and Gels from Electronic Materials ACS Nano 2013, 7, 962-977
22. Burrows, H. D.; Tapia, M. J.; Fonseca, S. M.; Pradhan, S.; Scherf, U.; Silva, C. L.; Pais, A. A. C. C.; Valente, A. J. M.; Schillén, K.; Alfredsson, V. Solubilization of Poly{1,4-Phenylene-[9,9-Bis(4-Phenoxy- Butylsulfonate)]Fluorene-2,7-Diyl} in Water by Nonionic Amphiphiles Langmuir 2009, 25, 5545-5556
23. Burrows, H. D.; Knaapila, M.; Monkman, A. P.; Tapia, M. J.; Fonseca, S. M.; Ramos, M. L.; Pyckhout-Hintzen, W.; Pradhan, S.; Scherf, U. 20, 104210-104217 Structural Studies on Cationic Poly{9,9-bis[6-(N,N,N- Trimethylammonium)Alkyl]Fluorene-co-1,4-Phenylene} Iodides in Aqueous Solutions in the Presence of the Nonionic Surfactant Pentaethyleneglycol Monododecyl Ether (C12E5) J. Phys.: Condens. Matter 2008, 20, 104210-104217
24. Chen, L.-H.; Xu, S.; McBranch, D.; Whitten, D. Tuning the Properties of Conjugated Polyelectrolytes through Surfactant Complexation J. Am. Chem. Soc. 2000, 122, 9302-9303
25. Chang, Y.-M.; Zhu, R.; Richard, E.; Chen, C.-C.; Li, G.; Yang, Y. Electrostatic Self-Assembly Conjugated PolyelectrolyteSurfactant Complex as an Interlayer for High Performance Polymer Solar Cells Adv. Funct. Mater. 2012, 22, 3284-3289
26. Pace, G.; Tu, G. L.; Fratini, E. Poly(9,9-dioctylfluorene)-Based Conjugated Polyelectrolyte: Extended pi-Electron Conjugation Induced by Complexation with a Surfactant Zwitterion Adv. Mater. 2010, 22, 2073-2077
27. Burrows, H. D.; Fonseca, S. M.; Dias, F. B.; Seixas de Melo, J.; Monkman, A. P.; Scherf, U.; Pradhan, S. Singlet Excitation Energy Harvesting and Triplet Emission in the Self Assembled System Poly{1,4-phenylene-[9,9-bis(4-phenoxy- butylsulfonate)]fluorene-2,7 diyl}copolymer/tris(bipyridyl)ruthenium(II) in Aqueous Solution Adv. Mater. 2009, 21, 1155-1159
28. Bricaud, Q.; Fabre, R. M.; Brookins, R. N.; Schanze, K. S.; Reynolds, J. R. Energy Transfer between Conjugated Polyelectrolytes in Layer-by-Layer Assembled Films Langmuir 2011, 27, 5021-5028
29. Wang, L.; Puodziukynaite, E.; Vary, R. P.; Grumstrup, E. M.; Walczak, R. M.; Zolotarskaya, O. Y.; Schanze, K. S.; Reynolds, J. R.; Papanikolas, J. M. Competition between Ultrafast Energy Flow and Electron Transfer in a Ru(II)-Loaded Polyfluorene Light-Harvesting Polymer J. Phys. Chem. Lett. 2012, 3, 2453-2457
30. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3 rd ed.; Springer: Berlin, Heidelberg, New York, 2006.
31. Woo, H. Y.; Liu, B.; Kohler, B.; Korystov, D.; Mikhailovsky, A.; Bazan, G. C. Solvent Effects on the Two-Photon Absorption of Distyrylbenzene Chromophores J. Am. Chem. Soc. 2005, 127, 14721-14729
32. Garner, L. E.; Park, J.; Dyar, S. M.; Chworos, A.; Sumner, J. J.; Bazan, G. C. Modification of the Optoelectronic Properties of Membranes via Insertion of Amphiphilic Phenylenevinylene Oligoelectrolytes J. Am. Chem. Soc. 2010, 132, 10042-10052
33. Hou, H.; Chen, X.; Thomas, A. W.; Catania, C.; Kirchhofer, N. D.; Garner, L. E.; Han, A.; Bazan, G. C. Conjugated Oligoelectrolytes Increase Power Generation in E. coli Microbial Fuel Cells Adv. Mater. 2013, 25, 1593-1597
34. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds Chem. Rev. 1995, 95, 2457-2483
35. Pina, J.; Seixas de Melo, J.; Burrows, H. D.; Maçanita, A. L.; Galbrecht, F.; Bünnagel, T.; Scherf, U. Alternating Binaphthyl-Thiophene Copolymers: Synthesis, Spectroscopy, and Photophysics and Their Relevance to the Question of Energy Migration versus Conformational Relaxation Macromolecules 2009, 42, 1710-1719
36. Costa, T.; Garner, L. E.; Knaapila, M.; Thomas, A. W.; Rogers, S. E.; Bazan, G. C.; Burrows, H. D. Aggregation Properties of p-Phenylene Vinylene Based Conjugated Oligoelectrolytes with Surfactants Langmuir 2013, 29, 10047-10058
37. Costa, T.; Di Paolo, R. E.; Garner, L.; Thomas, A. W.; Almeida, J. A. S.; Justino, L. L. G.; Maçanita, A. L.; Bazan, G. C.; Burrows, H. D. Separating Solvent and Conformational Effects on the Photophysics of a Homologous Progression of N-Terminated Phenylenevinylene Oligomers J. Phys. Chem. C 2013, 117, 18353-18366
38. Chen, Y.; Pu, K.-Y.; Fan, Q.-L.; Qi, X.-Y.; Huang, Y.-Q.; Lu, X.-M.; Huang, W. Water-Soluble Anionic Conjugated Polymers for Metal Ion Sensing: Effect of Interchain Aggregation J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 5057-5067
39. Lee, S. H.; Kömürlü, S.; Zhao, X.; Jiang, H.; Moriena, G.; Kleiman, V. D.; Schanze, K. S. Water-Soluble Conjugated Polyelectrolytes with Branched Polyionic Side Chains Macromolecules 2011, 44, 4742-4751
40. Tan, C.; Pinto, M. R.; Schanze, K. S. Photophysics, Aggregation and Amplified Quenching of a Water-Soluble Poly(Phenylene Ethynylene) Chem. Commun. 2002, 5, 446-447
41. WaÌŠgberg, T.; Liu, B.; Orädd, G.; Eliasson, B.; Edman, L. Cationic Polyfluorene: Conformation and Aggregation in a "Good" Solvent Eur. Polym. J. 2009, 45, 3228-3233
42. Burrows, H. D.; Lobo, V. M. M.; Pina, J.; Ramos, M. L.; Seixas de Melo, J.; Valente, A. J. M.; Tapia, M. J.; Pradhan, S.; Scherf, U.; Hintschich, S. I. Interactions Between Surfactants and {1,4-Phenylene-[9,9-Bis(4-Phenoxy- Butylsulfonate)]Fluorene-2,7-Diyl} Colloids Surf., A 2005, 270-271, 61-66
43. Knaapila, M.; Almásy, L.; Garamus, V. M.; Pearson, C.; Pradhan, S.; Petty, M. C.; Scherf, U.; Burrows, H. D.; Monkman, A. P. Solubilization of Polyelectrolytic Hairy-Rod Polyfluorene in Aqueous Solutions of Nonionic Surfactant J. Phys. Chem. B 2006, 110, 10248-10257
44. Burrows, H. D.; Lobo, V. M. M.; Pina, J.; Ramos, M. L.; Seixas de Melo, J.; Valente, A. J. M.; Tapia, M. J.; Pradhan, S.; Scherf, U. Fluorescence Enhancement of the Water-Soluble Poly{1,4-phenylene-[9,9-bis-(4- phenoxybutylsulfonate)]fluorene-2,7-diyl} Copolymer in n-Dodecylpentaoxyethylene Glycol Ether Micelles Macromolecules 2004, 37, 7425-7427
45. Pinto, S. M.; Burrows, H. D.; Pereira, M. M.; Fonseca, S. M.; Dias, F. B.; Mallavia, R.; Tapia, M. J. Singlet-Singlet Energy Transfer in Self-Assembled Systems of the Cationic Poly{9,9-Bis[6-N,N,N-Trimethylammonium)Hexyl]Fluorene- co-1,4-Phenylene} with Oppositely Charged Porphyrins J. Phys. Chem. B 2009, 113, 16093-16100
46. Burrows, H. D.; Tapia, M. J.; Silva, C. L.; Pais, A. A. C. C.; Fonseca, S. M.; Pina, J.; Seixas de Melo, J.; Wang, Y.; Marques, E. F.; Knaapila, M. Interplay of Electrostatic and Hydrophobic Effects with Binding of Cationic Gemini Surfactants and a Conjugated Polyanion: Experimental and Molecular Modelling Studies J. Phys. Chem. B 2007, 111, 4401-4410
47. Marques, A. T.; Burrows, H. D.; Seixas de Melo, J.; Valente, A. J. M.; Justino, L. L. G.; Scherf, U.; Fron, E.; Rocha, S.; Hofkens, J.; Snedden, E. W. Spectroscopic Properties, Excitation, and Electron Transfer in an Anionic Water-Soluble Poly(Fluorene-alt-Phenylene)-Perylenediimide Copolymer J. Phys. Chem. B 2012, 116, 7548-7559
48. Pina, J.; Seixas de Melo, J. S.; Koenen, N.; Scherf, U. Chain Length Dependent Excited-State Decay Processes of Diluted PF2/6 Solutions J. Phys. Chem. B 2013, 117, 7370-7380
49. Attar, H. A. A.; Monkman, A. P. The Effect of Surfactant on Water Soluble Conjugated-Polymer Used in Biosensor J. Phys. Chem. B 2007, 111, 12418-12426
50. Attar, H. A. A.; Monkman, A. P. Effect of Surfactant on FRET and Quenching in DNA Sequence Detection Using Conjugated Polymers Adv. Funct. Mater. 2008, 18, 2498-2509
51. Di Paolo, R. E.; Burrows, H. D.; Morgado, J.; Maçanita, A. L. Photodynamics of a PV Trimer in High-Viscosity Solvents and in PMMA Films: A New Insight into Energy Transfer versus Conformational Relaxation in Conjugated Polymers ChemPhysChem 2009, 10, 448-454
52. Dias, F. B.; Maçanita, A. L.; Seixas de Melo, J. S.; Burrows, H. D.; Guntner, R.; Scherf, U.; Monkman, A. P. Picosecond Conformational Relaxation of Singlet Excited Polyfluorene in Solution J. Chem. Phys. 2003, 118, 7119
53. Beljonne, D.; Pourtois, G.; Silva, C.; Hennebicq, E.; Herz, L. M.; Friend, R. H.; Scholes, G. D.; Setayesh, S.; Mullen, K.; Brédas, J.-L. Interchain vs. Intrachain Energy Transfer in Acceptor Capped Conjugated Polymers Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10982-10987
54. Nguyen, T.-Q.; Doan, V.; Schwartz, B. J. Conjugated polymer aggregates in solution: Control of interchain interactions J. Chem. Phys. 1999, 110, 4068-4078
55. Holmberg, K.; Jönsson, B.; Kronberg, B.; Lindman, B. Surfactant and Polymers in Aqueous Solution, 2 nd ed.; John Wiley & Sons, Ltd.: Chichester, U.K., 2003.
56. Bartholomew, G. P.; Bazan, G. C. Bichromophoric Paracyclophanes: Models for Interchromophore Delocalization Acc. Chem. Res. 2001, 34, 30-39