Complexation of fluorescent tetraphenylthiophene-derived ammonium chloride to poly(N -isopropylacrylamide) with sulfonate terminal: Aggregation-induced emission, critical micelle concentration, and lower critical solution temperature

Langmuir

Volumn 28, Issue 44, 2012, Pages 15725-15735

  Yang, Chih Min ^a   Lai, Yi Wei ^a   Kuo, Shiao Wei ^a   Hong, Jin Long ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATION-INDUCED EMISSIONS; AMMONIUM CHLORIDE; AMPHIPHILIC POLYMERS; AMPHIPHILICS; CRITICAL MICELLE CONCENTRATION (CMC); DILUTE AQUEOUS SOLUTION; EMISSION INTENSITY; HIGH TEMPERATURE; IONIC BONDS; ISOPROPYLACRYLAMIDE; LOWER CRITICAL SOLUTION TEMPERATURE; MOLAR RATIO; ROOM TEMPERATURE;

ACRYLIC MONOMERS; CHLORINE COMPOUNDS; CRITICAL MICELLE CONCENTRATION; FLUORESCENCE; MICELLES;

AMMONIUM COMPOUNDS;

ACRYLAMIDE DERIVATIVE; AMMONIUM CHLORIDE; POLY(N ISOPROPYLACRYLAMIDE); POLY(N-ISOPROPYLACRYLAMIDE); POLYMER; SULFONIC ACID DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; MICELLE; SOLUTION AND SOLUBILITY; SYNTHESIS; TEMPERATURE;

ACRYLAMIDES; AMMONIUM CHLORIDE; FLUORESCENCE; MICELLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYMERS; SOLUTIONS; SULFONIC ACIDS; TEMPERATURE; THIOPHENES;

EID: 84868575294     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la303783n     Document Type: Article

References (47)

1. Schatz, C.; Louguet, S.; Le Meins, J.-F.; Lecommandoux, S. Polysaccharide-block-polypeptide Copolymer Vesicles: Towards Synthetic Viral Capsids Angew. Chem., Int. Ed. 2009, 48, 2572-2575
2. Meng, F.; Zhong, Z.; Feijen, J. Stimuli-Responsive Polymers for Programmed Drug Delivery Biomacromolecules 2009, 10, 197-209
3. Vriezema, D. M.; Aragonès, M. C.; Elemans, J. A. A. W.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Self-Assembled Nanoreactors Chem. Rev. 2005, 105, 1445-1490
4. Wang, Y.; Xu, H.; Zhang, X. Tuning the Amphiphilicity of Building Blocks: Controlled Self-Assembly and Disassembly for Functional Supramolecular Materials Adv. Mater. 2009, 21, 2849-2864
5. Rapoport, N. Physical Stimuli-Responsive Polymeric Micelles for Anti-Cancer Drug Delivery Prog. Polym. Sci. 2007, 32, 962-990
6. Allen, C.; Maysinger, D.; Eisenberg, A. Nano-Engineering Block Copolymer Aggregates for Drug Delivery Colloids Surf. B 1999, 16, 3-27
7. Zheng, X. M.; Jiang, T.; He, F. Synthesis and Characterization of PNIPAM- b -Polycarbonate copolymers as Self-assembled Thermosensitive Micelles for Drug Delivery Acta Polym. Sin. 2011, 8, 895-902
8. Scarpa, J. S.; Mueller, D. D.; Klotz, I. M. Slow Hydrogen-Deuterium Exchange in a Non-α-Helical Polyamide J. Am. Chem. Soc. 1967, 89, 6024-6030
9. Schild, H. G. Poly(N -isopropylacrylamide): Experiment, Theory and Application Prog. Polym. Sci. 1992, 17, 163-249
10. Winnik, F. M. Phase Transition of Aqueous Poly(N -isopropylacrylamide) Solutions: a Study by Non-Radiative Energy Transfer Polymer 1990, 31, 2125-2134
11. Ringsdorf, H.; Simon, J.; Winnik, F. M. Hydrophobically-Modified Poly(N -isopropylacrylamides) in Water: Probing of the Microdomain Composition by Nonradiative Energy Transfer Macromolecules 1992, 25, 5353-5361
12. Chee, C. K.; Rimmer, S.; Soutar, I.; Swanson, L. Fluorescence Investigations of the Thermally Induced Conformational Transition of Poly(N -isopropylacrylamide) Polymer 2001, 42, 5079-5087
13. Rimmer, S.; Soutar, I.; Swanson, L. Switching the Conformational Behaviour of Poly(N -isopropylacrylamide) Polym. Int. 2009, 58, 273-278
14. Matsuyama, A.; Tanaka, F. Theory of Solvation-Induced Reentrant Coil-Globule Transition of an Isolated Polymer Chain J. Chem. Phys. 1991, 94, 781-786
15. Wu, C.; Zhou, S. Thermodynamically Stable Globule State of a Single Poly(N -isopropylacrylamide) Chain in Water Macromolecules 1995, 28, 5388-5390
16. Okada, Y.; Tanaka, F. Cooperative Hydration, Chain Collapse, and Flat LCST Behavior in Aqueous Poly(N -isopropylacrylamide) Solutions Macromolecules 2005, 38, 4465-4471
17. Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Aggregation-Induced Emission of 1-Methyl-1,2,3,4,5-pentaphenylsilole Chem. Commun. 2001, 1740-1741
18. Chen, H. Y.; Lam, W. Y.; Luo, J. D.; Ho, Y. L.; Tang, B. Z.; Zhu, D. B.; Wong, M.; Kwok, H. S. Highly Efficient Organic Light-Emitting Diodes with a Silole-Based Compound Appl. Phys. Lett. 2002, 81, 574-576
19. Chen, J.; Law, C. C. W.; Lam, J. W. Y.; Dong, Y.; Lo, S. M. F.; Williams, I. D.; Zhu, D.; Tang, B. Z. Synthesis, Light Emission, Nanoaggregation, and Restricted Intramolecular Rotation of 1,1-Substituted 2,3,4,5-Tetraphenylsiloles Chem. Mater. 2003, 15, 1535-1546
20. Chen, J.; Xie, Z.; Lam, J. W. Y.; Law, C. C. W.; Tang, B. Z. Silole-Containing Polyacetylenes: Synthesis, Thermal Stability, Light Emission, Nanodimensional Aggregation, and Restricted Intramolecular Rotation Macromolecules 2003, 36, 1108-1117
21. Chen, J.; Peng, H.; Law, C. C. W.; Dong, Y.; Lam, J. W. Y.; Williams, I. D.; Tang, B. Z. Hyperbranched Poly(phenylenesilolene)s: Synthesis, Thermal Stability, Electronic Conjugation, Optical Power Limiting, and Cooling-Enhanced Light Emission Macromolecules 2003, 36, 4319-4327
22. Dong, S.; Li, Z.; Qin, J. New Carbazole-Based Fluorophores: Synthesis, Characterization, and Aggregation-Induced Emission Enhancement J. Phys. Chem. B 2009, 113, 434-441
23. Yuan, C. X.; Tao, X. T.; Wang, L.; Yang, J. X.; Jiang, M. H. Fluorescent Turn-On Detection and Assay of Protein Based on Lambda (Λ)-Shaped Pyridinium Salts with Aggregation-Induced Emission Characteristics J. Phys. Chem. C 2009, 113, 6809-6814
24. Liu, Y.; Tao, X.; Wang, F.; Dang, X.; Zou, D.; Ren, Y.; Jiang, M. Aggregation-Induced Emissions of Fluorenonearylamine Derivatives: A New Kind of Materials for Nondoped Red Organic Light-Emitting Diodes J. Phys. Chem. C 2008, 112, 3975-3981
25. Xu, B.; Chi, Z.; Yang, Z.; Chen, J.; Deng, S.; Li, H.; Li, X.; Zhang, Y.; Xu, N.; Xu, J. Facile Synthesis of a New Class of Aggregation-Induced Emission Materials Derived from Triphenylethylene J. Mater. Chem. 2010, 20, 4135-4141
26. Zhao, Z.; Chen, S.; Lam, J. W. Y.; Lu, P.; Zhong, Y.; Wong, K. S.; Kwok, H. S.; Tang, B. Z. Creation of Highly Efficient Solid Emitter by Decorating Pyrene Core with AIE-Active Tetraphenylethene Peripheries Chem. Commun. 2010, 46, 2221-2223
27. Tang, L.; Jin, J. K.; Qin, A.; Yuan, W. Z.; Mao, Y.; Mei, J.; Sun, J. Z.; Tang, B. Z. A Fluorescent Thermometer Operating in Aggregation-Induced Emission Mechanism: Probing Thermal Transitions of PNIPAM in Water Chem. Commun. 2009, 4974-4976
28. Liu, J.; Zhong, Y.; Lam, J. W. Y.; Lu, P.; Hong, Y.; Yu, Y.; Yue, Y.; Faisal, M.; Sung, H. H. Y.; Williams, I. D.; Wong, K. S.; Tang, B. Z. Hyperbranched Conjugated Polysiloles: Synthesis, Structure, Aggregation-Enhanced Emission, Multicolor Fluorescent Photopatterning, and Superamplified Detection of Explosives Macromolecules 2010, 43, 4921-4936
29. Qin, A.; Lam, J. W. Y.; Tang, L.; Jim, C. K. W.; Zhao, H.; Sun, J.; Tang, B. Z. Polytriazoles with Aggregation-Induced Emission Characteristics: Synthesis by Click Polymerization and Application as Explosive Chemosensors Macromolecules 2009, 42, 1421-1424
30. Chien, R. H.; Lai, C. T.; Hong, J. L. Enhanced Aggregation Emission of Vinyl Polymer Containing Tetraphenylthiophene Pendant Group J. Phys. Chem. C 2011, 115, 5958-5965
31. Lai, C. T.; Hong, J. L. Aggregation-Induced Emission in Tetraphenylthiophene-Derived Organic Molecules and Vinyl Polymer J. Phys. Chem. B 2010, 114, 10302-10310
32. Chou, C. A.; Chien, R. H.; Lai, C. T.; Hong, J. L. Complexation of bulky Camphorsulfonic Acid to Enhance Emission of Organic and Polymeric Fluorophores with Inherent Quinoline Moiety Chem. Phys. Lett. 2010, 501, 80-86
33. Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Aggregation-Induced Emission: Phenomenon, Mechanism and Applications Chem. Commun. 2009, 4332-4353
34. Liu, J.; Lam, J. W. Y.; Tang, B. Z. Aggregation-Induced Emission of Silole Molecules and Polymers: Fundamental and Applications J. Inorg. Organomet. Polym. 2009, 19, 249-285
35. Qin, A.; Lam, J. W. Y.; Tang, B. Z. Luminogenic Polymers with Aggregation-Induced Emission Characteristics Prog. Polym. Sci. 2012, 37, 182-209
36. Lai, C. T.; Chien, R. H.; Kuo, S. W.; Hong, J. L. Tetraphenylthiophene- Functionalized Poly(N -isopropylacrylamide): Probing LCST with Aggregation-Induced Emission Macromolecules 2011, 44, 6546-6556
37. Lai, Y.-W; Kuo, S.-W.; Hong, J.-L. Complexing AIEE-Active Tetraphenylthiophene Fluorophore to Poly(N -isopropylacrylamide): Fluorescence Responses toward Acid, Base and Metal ions RSC Adv. 2012, 2, 8194-8200
38. Li, H.; Chi, Z.; Zhang, X.; Xu, B.; Liu, S.; Zhang, Y.; Xu, J. New Red Aggregation-Induced Emission Enhancement Compounds with High Thermal Stabilities and Excellent Non-doped Red OLED Performances Were Synthesized Chem. Commun. 2011, 47, 11273-11275
39. Ruthard, C.; Maskos, M.; Kolb, U.; Gröhn, F. Finite-Size Networks from cylindrical Polyelectrolyte Brushes and Porphyrins Macromolecules 2009, 42, 830-840
40. Egawa, Y.; Hayashida, R.; Anzai, J. pH-Induced Interconversion between J-Aggregates and H-Aggregates of 5,10,15,20-Tetrakis(4-sulfonatophenyl)porphyrin in Polyelectrolyte Multilayer Films Langmuir 2007, 23, 13146-13150
41. Kubát, P.; Lang, K.; Janda, P.; Anzenbacher, P. Interaction of Porphyrins with a Dendrimer Template: Self-Aggregation Controlled by pH Langmuir 2005, 21, 9714-9720
42. Moreno-Villoslada, I.; Fuenzalida, J. P.; Tripailaf, G.; Araya-Hermosilla, R.; Pizarro, G. C.; Marambio, O. G.; Nishide, H. Comparative Study of the Self-Aggregation of Rhodamine 6G in the Presence of Poly(sodium 4-styrenesulfonate), Poly(N -phenylmaleimide- co -acrylic acid), Poly(styrene- alt -maleic acid), and Poly(sodium acrylate) J. Phys. Chem. B 2010, 114, 11983-11992
43. Moreno-Villoslada, I.; Torres, C.; González, F.; Shibue, T.; Nishide, H. Binding of Methylene Blue to Polyelectrolytes Containing Sulfonate Groups Macromol. Chem. Phys. 2009, 210, 1167-1175
44. Chien, R. H.; Lai, J. T.; Hong, J. L. Complexation of tetraphenylthiophene-Derived Ammonium Chloride to Poly(sodium vinylsulfonate) Polyelectrolytes: Aggregation-Induced Emission Enhancement and Long-Range Interaction Macromol. Chem. Phys. 2012, 213, 666
45. Tang, W.; Chen, J.; Liu, Z.-T.; Liu, Z.-W. Synthesis and Characterization of Thermo-responsive Poly(N -vinyl-2-pyrrolidinone)- block -poly(N -isopropylacrylamide) Micelles J. Macromol. Sci., Part A: Pure Appl. Chem. 2010, 47, 1026-1031
46. Shi, L. J.; Zhao, M. W.; Zheng, L. Q. Micelle Formation by N -Alkyl- N -Methylpyrrolidinium Bromide in Ethylammonium Nitrate Colloids Surf. A 2011, 392, 305-312
47. Shinoda, K. Colloidal Surfactant; Academic Press: New York, 1963.