Photomodulated fluorescence of supramolecular assemblies of sulfonatocalixarenes and tetraphenylethene

ACS Nano

Volumn 8, Issue 2, 2014, Pages 1609-1618

  Jiang, Bang Ping ^a   Guo, Dong Sheng ^a   Liu, Yan Cen ^a   Wang, Kun Peng ^a   Liu, Yu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

fluorescent nanoparticle; photoswitching; sulfonatocalixarenes; tetraphenylethene

Indexed keywords

EID: 84894623343     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn405923b     Document Type: Article

References (80)

1. Gill, R.; Zayats, M.; Willner, I. Semiconductor Quantum Dots for Bioanalysis Angew. Chem., Int. Ed. 2008, 47, 7602-7625
2. Medintz, I. L.; Uyeda, H. T.; Goldman, E. R.; Mattoussi, H. Quantum Dot Bioconjugates for Imaging, Labelling and Sensing Nat. Mater. 2005, 4, 435-446
3. Tian, Z.; Li, A. D. Q. Photoswitching-Enabled Novel Optical Imaging: Innovative Solutions for Real-World Challenges in Fluorescence Detections Acc. Chem. Res. 2013, 46, 269-279
4. Gorris, H. H.; Wolfbeis, O. S. Photon-Upconverting Nanoparticles for Optical Encoding and Multiplexing of Cells, Biomolecules, and Microspheres Angew. Chem., Int. Ed. 2013, 52, 3584-3600
5. Zhu, L.; Wu, W.; Zhu, M.-Q.; Han, J. J.; Hurst, J. K.; Li, A. D. Q. Reversibly Photoswitchable Dual-Color Fluorescent Nanoparticles as New Tools for Live-Cell Imaging J. Am. Chem. Soc. 2007, 129, 3524-3526
6. Dennis, A. M.; Rhee, W. J.; Sotto, D.; Dublin, S. N.; Bao, G. Quantum Dot-Fluorescent Protein FRET Probes for Sensing Intracellular pH ACS Nano 2012, 6, 2917-2924
7. Wu, C.; Bull, B.; Szymanski, C.; Christensen, K.; McNeill, J. Multicolor Conjugated Polymer Dots for Biological Fluorescence Imaging ACS Nano 2008, 2, 2415-2423
8. Petkau, K.; Kaeser, A.; Fischer, I.; Brunsveld, L.; Schenning, A. P. H. J. Pre-and Postfunctionalized Self-Assembled π-Conjugated Fluorescent Organic Nanoparticles for Dual Targeting J. Am. Chem. Soc. 2011, 133, 17063-17071
9. Feng, X.; Liu, L.; Wang, S.; Zhu, D. Water-Soluble Fluorescent Conjugated Polymers and Their Interactions with Biomacromolecules for Sensitive Biosensors Chem. Soc. Rev. 2010, 39, 2411-2419
10. Zhang, K.; Zhou, H.; Mei, Q.; Wang, S.; Guan, G.; Liu, R.; Zhang, J.; Zhang, Z. Instant Visual Detection of Trinitrotoluene Particulates on Various Surfaces by Ratiometric Fluorescence of Dual-Emission Quantum Dots Hybrid J. Am. Chem. Soc. 2011, 133, 8424-8427
11. 2 Sensing Probe Based on Cell-Penetrating Phosphorescent Nanoparticles ACS Nano 2011, 5, 5499-5508
12. Chan, Y.-H.; Wu, C.; Ye, F.; Jin, Y.; Smith, P. B.; Chiu, D. T. Development of Ultrabright Semiconducting Polymer Dots for Ratiometric pH Sensing Anal. Chem. 2011, 83, 1448-1455
13. 2+ Ions Chem. Commun. 2009, 1736-1738
14. Pecher, J.; Mecking, S. Nanoparticles of Conjugated Polymers Chem. Rev. 2010, 110, 6260-6279
15. Thomas, S. W.; Joly, G. D.; Swager, T. M. Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers Chem. Rev. 2007, 107, 1339-1386
16. Jatsch, A.; Schillinger, E.-K.; Schmid, S.; Böauerle, P. Biomolecule Assisted Self-Assembly of π-Conjugated Oligomers J. Mater. Chem. 2010, 20, 3563-3578
17. Landfester, K. Miniemulsion Polymerization and the Structure of Polymer and Hybrid Nanoparticles Angew. Chem., Int. Ed. 2009, 48, 4488-4507
18. Jaskiewicz, K.; Larsen, A.; Lieberwirth, I.; Koynov, K.; Meier, W.; Fytas, G.; Kroeger, A.; Landfester, K. Probing Bioinspired Transport of Nanoparticles into Polymersomes Angew. Chem., Int. Ed. 2012, 51, 4613-4617
19. Zhang, X.; Yu, J.; Rong, Y.; Ye, F.; Chiu, D. T.; Uvdal, K. High-Intensity Near-IR Fluorescence in Semiconducting Polymer Dots Achieved by Cascade FRET Strategy Chem. Sci. 2013, 4, 2143-2151
20. Haase, M.; Schäfer, H. Upconverting Nanoparticles Angew. Chem., Int. Ed. 2011, 50, 5808-5829
21. Morgan, T. T.; Muddana, H. S.; Altinoglu, E. I.; Rouse, S. M.; Tabakivic, T.; Tabouillot, T.; Russin, T. J.; Shanmugavelandy, S. S.; Butler, P. J.; Eklund, P. C. et al. Encapsulation of Organic Molecules in Calcium Phosphate Nanocomposite Particles for Intracellular Imaging and Drug Delivery Nano Lett. 2008, 8, 4108-4115
22. x: Quick and Easy Synthesis of a Nanoscale Luminescent Biomarker Angew. Chem., Int. Ed. 2010, 49, 632-637
23. Chan, Y.-H.; Ye, F.; Gallina, M. E.; Zhang, X.; Jin, Y.; Wu, I.-C.; Chiu, D. T. Hybrid Semiconducting Polymer Dot-Quantum Dot with Narrow-Band Emission, Near-Infrared Fluorescence, and High Brightness J. Am. Chem. Soc. 2012, 134, 7309-7312
24. Burns, A.; Ow, H.; Wiesner, U. Fluorescent Core-Shell Silica Nanoparticles: Towards "Lab on a Particle" Architectures for Nanobiotechnology Chem. Soc. Rev. 2006, 35, 1028-1042
25. An, B.-K.; Kwon, S.-K.; Jung, S.-D.; Park, S. Y. Enhanced Emission and Its Switching in Fluorescent Organic Nanoparticles J. Am. Chem. Soc. 2002, 124, 14410-14415
26. Jana, A.; Devi, K. S. P.; Maiti, T. K.; Singh, N. D. P. Perylene-3-ylmethanol: Fluorescent Organic Nanoparticles as a Single-Component Photoresponsive Nanocarrier with Real-Time Monitoring of Anticancer Drug Release J. Am. Chem. Soc. 2012, 134, 7656-7659
27. Zhao, Q.; Li, K.; Chen, S.; Qin, A.; Ding, D.; Zhang, S.; Liu, Y.; Liu, B.; Sun, J. Z.; Tang, B. Z. Aggregation-Induced Red-NIR Emission Organic Nanoparticles as Effective and Photostable Fluorescent Probes for Bioimaging J. Mater. Chem. 2012, 22, 15128-15135
28. Qiu, F.; Zhu, Q.; Tong, G.; Zhu, L.; Wang, D.; Yan, D.; Zhu, X. Highly Fluorescent Core-Shell Hybrid Nanoparticles Templated by a Unimolecular Star Conjugated Polymer for a Biological Tool Chem. Commun. 2012, 48, 11954-11956
29. Wu, C.; Chiu, D. T. Highly Fluorescent Semiconducting Polymer Dots for Biology and Medicine Angew. Chem., Int. Ed. 2013, 52, 3086-3109
30. Jin, Y.; Ye, F.; Zeigler, M.; Wu, C.; Chiu, D. T. Near-Infrared Fluorescent Dye-Doped Semiconducting-Polymer Dots ACS Nano 2011, 5, 1468-1475
31. Kaeser, A.; Fischer, I.; Abbel, R.; Besenius, P.; Dasgupta, D.; Gillisen, M. A. J.; Portale, G.; Stevens, A. L.; Herz, L. M.; Schenning, A. P. H. J. Side Chains Control Dynamics and Self-Sorting in Fluorescent Organic Nanoparticles ACS Nano 2013, 7, 408-416
32. Luo, J.; Xie, Z.; Lam, J.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D. et al. Aggregation-Induced Emission of 1-Methyl-1,2,3,4,5-pentaphenylsilole Chem. Commun. 2001, 1740-1741
33. Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Aggregation-Induced Emission: Phenomenon, Mechanism and Applications Chem. Commun. 2009, 4332-4353
34. Kumar, M.; George, S. J. Green Fluorescent Organic Nanoparticles by Self-Assembly Induced Enhanced Emission of a Naphthalene Diimide Bolaamphiphile Nanoscale 2011, 3, 2130-2133
35. Chen, S.; Liu, J.; Liu, Y.; Su, H.; Hong, Y.; Jim, C. K. W.; Kwok, R. T. K.; Zhao, N.; Qin, W.; Lam, J. W. Y. et al. An AIE-Active Hemicyanine Fluorogen with Stimuli-Responsive Red/Blue Emission: Extending the pH Sensing range by "Switch + Knob" Effect Chem. Sci. 2012, 3, 1804-1809
36. Patra, A.; Scherf, U. Fluorescent Microporous Organic Polymers: Potential Testbed for Optical Applications Chem.-Eur. J. 2012, 18, 10074-10080
37. An, B.-K.; Kwon, S.-K.; Park, S. Y. Photopatterned Arrays of Fluorescent Organic Nanoparticles Angew. Chem., Int. Ed. 2007, 46, 1978-1982
38. Wang, M.; Zhang, G.; Zhang, D.; Zhu, D.; Tang, B. Z. Fluorescent Bio/chemosensors Based on Silole and Tetraphenylethene Luminogens with Aggregation-Induced Emission Feature J. Mater. Chem. 2010, 20, 1858-1867
39. Hong, Y.; Häussler, M.; Lam, J.; Li, Z.; Sin, K.; Dong, Y.; Tong, H.; Liu, J.; Qin, A.; Renneberg, R. et al. Label-Free Fluorescent Probing of G-Quadruplex Formation and Real-Time Monitoring of DNA Folding by a Quaternized Tetraphenylethene Salt with Aggregation-Induced Emission Characteristics Chem.-Eur. J. 2008, 14, 6428-6437
40. Tong, H.; Hong, Y.; Dong, Y.; Häussler, M.; Li, Z.; Lam, J. W. Y.; Dong, Y.; Sung, H. H.-Y.; Williams, I. D.; Tang, B. Z. Protein Detection and Quantitation by Tetraphenylethene-Based Fluorescent Probes with Aggregation-Induced Emission Characteristics J. Phys. Chem. B 2007, 111, 11817-11823
41. Wang, M.; Gu, X.; Zhang, G.; Zhang, D.; Zhu, D. Convenient and Continuous Fluorometric Assay Method for Acetylcholinesterase and Inhibitor Screening Based on the Aggregation-Induced Emission Anal. Chem. 2009, 81, 4444-4449
42. Guo, D.-S.; Liu, Y. Calixarene-Based Supramolecular Polymerization in Solution Chem. Soc. Rev. 2012, 41, 5907-5921
43. Wang, K.; Guo, D.-S.; Liu, Y. Temperature-Controlled Supramolecular Vesicles Modulated by p-Sulfonatocalix[5]arene with Pyrene Chem.-Eur. J. 2010, 16, 8006-8011
44. Wang, K.; Guo, D.-S.; Wang, X.; Liu, Y. Multistimuli Responsive Supramolecular Vesicles Based on the Recognition of p-Sulfonatocalixarene and Its Controllable Release of Doxorubicin ACS Nano 2011, 5, 2880-2994
45. Guo, D.-S.; Jiang, B.-P.; Wang, X.; Liu, Y. Calixarene-Induced Aggregation of Perylene Bisimides Org. Biomol. Chem. 2012, 10, 720-723
46. Guo, D.-S.; Chen, K.; Zhang, H.-Q.; Liu, Y. Nano-Supramolecular Assemblies Constructed from Water-Soluble Bis-(calix[5]arenes) with Porphyrins and Their Photoinduced Electron Transfer Properties Chem.-Asian J. 2009, 4, 436-445
47. Wang, K.; Guo, D.-S.; Liu, Y. Controlled Self-Assembly by Mono-p-sulfonatocalix[ n ]arenes and Bis-p-sulfonatocalix[ n ]arenes Chem.-Eur. J. 2012, 18, 8758-8764
48. Guo, D.-S.; Wang, K.; Wang, Y.-X.; Liu, Y. Cholinesterase-Responsive Supramolecular Vesicle J. Am. Chem. Soc. 2012, 134, 10244-10250
49. Francisco, V.; Basilio, N.; Garcia-Rio, L.; Leis, J. R.; Maques, E. F.; Vázquez-Vázquez, C. Novel Catanionic Vesicles from Calixarene and Single-Chain Surfactant Chem. Commun. 2010, 46, 6551-6553
50. Moschetto, G.; Lauceri, R.; Gulino, F. G.; Sciotto, D.; Purrello, R. Non-covalent Synthesis in Aqueous Solution of Discrete Multi-porphyrin Aggregates with Programmable Stoichiometry and Sequence J. Am. Chem. Soc. 2002, 124, 14536-14537
51. Costanzo, L. D.; Geremia, S.; Randaccio, L.; Purrello, R.; Lauceri, R.; Sciotto, D.; Gulino, F. G.; Pavone, V. Calixarene-Porphyrin Supramolecular Complexes: pH-Tuning of the Complex Stoichiometry Angew. Chem., Int. Ed. 2001, 40, 4245-4247
52. Lau, V.; Heyne, B. Calix[4]arene Sulfonate as a Template for Forming Fluorescent Thiazole Orange H-Aggregates Chem. Commun. 2010, 46, 3595-3597
53. Basilio, N.; Ǵmez, B.; García-Río, L.; Francisco, V. Using Calixarenes To Model Polyelectrolyte Surfactant Nucleation Sites Chem.-Eur. J. 2013, 19, 4570-4576
54. Basilio, N.; Francisco, V.; Garcia-Rio, L. Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-amphiphiles Int. J. Mol. Sci. 2013, 14, 3140-3157
55. Basilio, N.; García-Río, L. Sulfonated Calix[6]arene Host-Guest Complexes Induce Surfactant Self-Assembly Chem.-Eur. J. 2009, 15, 9315-9319
56. Basilio, N.; Martín-Pastor, M.; García-Río, L. Insights into the Structure of the Supramolecular Amphiphile Formed by a Sulfonated Calix[6]arene and Alkyltrimethylammonium Surfactants Langmuir 2012, 28, 6561-6568
57. Liu, J.; Jiang, N.; Ma, J.; Du, X. Insight into Unusual Downfield NMR Shifts in the Inclusion Complex of Acridine Orange with Cucurbit[7]uril Eur. J. Org. Chem. 2009, 4931-4938
58. Biedermann, F.; Elmalem, E.; Ghosh, I.; Nau, W. M.; Scherman, O. A. Strongly Fluorescent, Switchable Perylene Bis(diimide) Host-Guest Complexes with Cucurbit[8]uril in Water Angew. Chem., Int. Ed. 2012, 51, 7739-7743
59. Dsouza, R. N.; Pischel, U.; Nau, W. M. Fluorescent Dyes and Their Supramolecular Host-Guest Complexes with Macrocycles in Aqueous Solution Chem. Rev. 2011, 111, 7941-7980
60. Uchiyama, S.; Kawai, N.; de Silva, A. P.; Iwai, K. Fluorescent Polymeric AND Logic Gate with Temperature and pH as Inputs J. Am. Chem. Soc. 2004, 126, 3032-3033
61. Li, C.; Liu, S. Polymeric Assemblies and Nanoparticles with Stimuli-Responsive Fluorescence Emission Characteristics Chem. Commun. 2012, 48, 3262-3278
62. Qu, D.-H.; Wang, Q.-C.; Ma, X.; Tian, H. A [3]Rotaxane with Three Stable States That Responds to Multiple-Inputs and Displays Dual Fluorescence Addresses Chem.-Eur. J. 2005, 11, 5929-5937
63. Dube, H.; Ams, M. R.; Rebek, J., Jr. Supramolecular Control of Fluorescence through Reversible Encapsulation J. Am. Chem. Soc. 2010, 132, 9984-9985
64. Raymo, F. M.; Tomasulo, M. Electron and Energy Transfer Modulation with Photochromic Switches Chem. Soc. Rev. 2005, 34, 327-336
65. Tian, H.; Yang, S. J. Recent Progresses on Diarylethene Based Photochromic Switches Chem. Soc. Rev. 2004, 33, 85-97
66. Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Organic Chemistry: A Digital Fluorescent Molecular Photoswitch Nature 2002, 420, 759-760
67. Chung, J. W.; Yoon, S.-J.; Lim, S.-J.; An, B.-K.; Park, S. Y. Dual-Mode Switching in Highly Fluorescent Organogels: Binary Logic Gates with Optical/Thermal Inputs Angew. Chem., Int. Ed. 2009, 48, 7030-7034
68. Jiang, G.; Wang, S.; Yuan, W.; Zhao, Z.; Duan, A.; Xu, C.; Jiang, L.; Song, Y.; Zhu, D. Photo-and Proton-Dual-Responsive Fluorescence Switch Based on a Bisthienylethene-Bridged Naphthalimide Dimer and Its Application in Security Data Storage Eur. J. Org. Chem. 2007, 2064-2067
69. Schultz, A.; Laschat, S.; Diele, S.; Nimtz, M. Tetraphenylethene-Derived Columnar Liquid Crystals and Their Oxidative Photocyclization Eur. J. Org. Chem. 2003, 2829-2839
70. Aldred, P.; Li, C.; Zhu, M.-Q. Optical Properties and Photo-oxidation of Tetraphenylethene-Based Fluorophores Chem.-Eur. J. 2012, 18, 16037-16045
71. Huang, G.; Ma, B.; Chen, J.; Peng, Q.; Zhang, G.; Fan, Q.; Zhang, D. Dendron-Containing Tetraphenylethylene Compounds: Dependence of Fluorescence and Photocyclization Reactivity on the Dendron Generation Chem.-Eur. J. 2012, 18, 3886-3892
72. Guo, D.-S.; Wang, K.; Liu, Y. Selective Binding Behaviors of p-Sulfonatocalixarenes in Aqueous Solution J. Incl. Phenom. Macrocycl. Chem. 2008, 62, 1-21
73. Tong, H.; Hong, Y.; Dong, Y.; Häußler, M.; Lam, J. W. Y.; Li, Z.; Guo, Z.; Guo, Z.; Tang, B. Z. Fluorescent "Light-Up" Bioprobes Based on Tetraphenylethylene Derivatives with Aggregation-Induced Emission Characteristics Chem. Commun. 2006, 3705-3707
74. Wang, J.; Mei, J.; Hu, R.; Sun, J. Z.; Qin, A.; Tang, B. Z. Click Synthesis, Aggregation-Induced Emission, E / Z Isomerization, Self-Organization, and Multiple Chromisms of Pure Stereoisomers of a Tetraphenylethene-Cored Luminogen J. Am. Chem. Soc. 2012, 134, 9956-9966
75. Yu, W.-H.; Chen, C.; Hu, P.; Wang, B.-Q.; Redshaw, C.; Zhao, K.-Q. Tetraphenylethene-Triphenylene Oligomers with an Aggregation-Induced Emission Effect and Discotic Columnar Mesophase RSC Adv. 2013, 3, 14099-14105
76. Watanabe, S.; Kobayashi, A.; Kakimoto, M.; Imai, Y. Synthesis and Characterization of New Aromatic Polyesters and Polyethers Derived from 1,2-Bis(4-hydroxyphenyl)-1,2-diphenylethylene J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 909-915
77. Arena, G.; Contino, A.; Lombardo, G. G.; Sciotto, D. Water-Soluble Calix[6]arenes. Characterization of 5,11,17,23,29,35-Hexasulphonate-37,38,39,40, 41,42-hexahydroxy-calix[6]arene and Thermodynamic Study of Proton Complex Formation Thermochim. Acta 1995, 264, 1-11
78. Guo, D.-S.; Chen, S.; Qian, H.; Zhang, H.-Q.; Liu, Y. Electrochemical Stimulus-Responsive Supramolecular Polymer Based on Sulfonatocalixarene and Viologen Dimers Chem. Commun. 2010, 46, 2620-2622
79. Xu, X.; Lv, W.; Huang, J.; Li, J.; Tang, R.; Yan, J.; Yang, Q.; Qin, J.; Li, Z. Functionalization of Graphene by Tetraphenylethylene Using Nitrene Chemistry RSC Adv. 2012, 2, 7042-7047
80. Gu, Z.-Y.; Guo, D.-S.; Sun, M.; Liu, Y. Effective Enlargement of Fluorescence Resonance Energy Transfer of Poly-porphyrin Mediated by β-Cyclodextrin Dimers J. Org. Chem. 2010, 75, 3600-3607