A pH-responsive molecular switch with tricolor luminescence

ACS Applied Materials and Interfaces

Volumn 7, Issue 1, 2015, Pages 704-712

  Ahn, Hyungmin ^a   Hong, Jaewan ^a   Kim, Sung Yeon ^a   Choi, Ilyoung ^a   Park, Moon Jeong ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

fluorescence; multicolor luminescence; pH sensors; ratiometric; self assembly; tautomerism

Indexed keywords

BLOCK COPOLYMERS; COPOLYMERS; ENERGY GAP; FLUORESCENCE; LUMINESCENCE; PH; SELF ASSEMBLY;

CONJUGATION EFFECTS; FLUORESCENCE PROPERTIES; FLUORESCENT COLORS; MULTICOLOR LUMINESCENCES; NANOMETER LENGTH SCALE; RATIOMETRIC; TAUTOMERISM; THEORETICAL CALCULATIONS;

PH SENSORS;

CHLORINE; FLUORESCENT DYE; MACROGOL DERIVATIVE; MALEIMIDE DERIVATIVE; MICELLE; MONOMETHOXYPOLYETHYLENE GLYCOL; POLYMER; PROTON; SOLVENT; WATER;

CHEMISTRY; ELECTRON; ELECTRONICS; FLUORESCENCE MICROSCOPY; GENETIC PROCEDURES; LUMINESCENCE; MICELLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OSCILLOMETRY; PH; SPECTROFLUOROMETRY; STATIC ELECTRICITY; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

BIOSENSING TECHNIQUES; CHLORINE; ELECTRONICS; ELECTRONS; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; LUMINESCENCE; MAGNETIC RESONANCE SPECTROSCOPY; MALEIMIDES; MICELLES; MICROSCOPY, ELECTRON, TRANSMISSION; MICROSCOPY, FLUORESCENCE; OSCILLOMETRY; POLYETHYLENE GLYCOLS; POLYMERS; PROTONS; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; STATIC ELECTRICITY; WATER;

EID: 84921275611     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am5070188     Document Type: Article

References (47)

1. Korostynska, O.; Arshak, K.; Gill, E.; Arshak, A. Review on State-of-the-art in Polymer Based pH Sensors Sensors 2007, 7, 3027-3042
2. Krulwich, T. A.; Sachs, G.; Padan, E. Molecular Aspects of Bacterial pH Sensing and Homeostasis Nat. Rev. Microbiol. 2011, 9, 330-343
3. Ang, P. K.; Chen, W.; Wee, A. T. S.; Loh, K. P. Solution-Gated Epitaxial Graphene as pH Sensor J. Am. Chem. Soc. 2008, 130, 14392-14393
4. 2 for a Solid-State pH Sensor Electrochim. Acta 2010, 55, 2859-2864
5. 3 Nanoparticle-Based Conformable pH Sensor ACS Appl. Mater. Interfaces 2014, 6, 12226-12234
6. Wencel, D.; Abel, T.; McDonagh, C. Optical Chemical pH Sensors Anal. Chem. 2014, 86, 15-29
7. Fenzi, C.; Wilhelm, S.; Hirsch, T.; Wolfbeis, O. S. Optical Sensing of the Ionic Strength Using Photonic Crystals in a Hydrogel Matrix ACS Appl. Mater. Interfaces 2013, 5, 173-178
8. Baruah, M.; Qin, W.; Basarić, N.; Borggraeve, W. M. D.; Boens, N. BODIPY-Based Hydroxyaryl Derivatives as Fluorescent pH Probes J. Org. Chem. 2005, 70, 4152-4157
9. Ke, G.; Zhu, Z.; Wang, W.; Zou, Y.; Guan, Z.; Jia, S.; Zhang, H.; Wu, X.; Yang, C. J. A Cell-Surface-Anchored Ratiometric Fluorescent Probe for Extracellular pH Sensing ACS Appl. Mater. Interfaces 2014, 6, 15329-15334
10. You, S.; Cai, Q.; Mullen, K.; Yang, W.; Yin, M. pH-Sensitive Unimolecular Fluorescent Polymeric Micelles: from Volume Phase Transition to Optical Response Chem. Commun. 2014, 50, 823-825
11. Wu, Y.; Chakrabortty, S.; Gropeanu, R. A.; Wilhelmi, J.; Xu, Y.; Er, K. S.; Kuan, S. L.; Koynov, K.; Chan, Y.; Weil, T. pH-Responsive Quantum Dots via an Albumin Polymer Surface Coating J. Am. Chem. Soc. 2010, 132, 5012-5014
12. Medintz, I. L.; Stewart, M. H.; Trammell, S. A.; Susumu, K.; Delehanty, J. B.; Mei, B. C.; Melinger, J. S.; Blanco-Canosa, J. B.; Dawson, P. E.; Mattoussi, H. Quantum-Dot/Dopamine Bioconjugates Function as Redox Coupled Assemblies for in vitro and Intracellular pH Sensing Nat. Mater. 2010, 9, 676-684
13. Frasco, M. F.; Chaniotakis, N. Semiconductor Quantum Dots in Chemical Sensors and Biosensors Sensors 2009, 9, 7266-7286
14. Fan, J.; Hu, M.; Zhan, P.; Peng, X. Energy Transfer Cassettes Based on Organic Fluorophores: Construction and Applications in Ratiometric Sensing Chem. Soc. Rev. 2013, 42, 29-43
15. Chen, S.; Hong, Y.; Liu, Y.; Liu, J.; Leung, C. W.; Li, M.; Kwok, R. T.; Zhao, E.; Lam, J. W.; Yu, Y.; Tang, B. Z. Full-Range Intracellular pH Sensing by an Aggregation-Induced Emission-Active Two-Channel Ratiometric Fluorogen J. Am. Chem. Soc. 2013, 135, 4926-4929
16. Shi, W.; Li, X.; Ma, H. A Tunable Ratiometric pH Sensor Based on Carbon Nanodots for the Quantitative Measurement of the Intracellular pH of Whole Cells Angew. Chem., Int. Ed. 2012, 124, 6538-6541
17. Wan, S.; Zheng, Y.; Shen, J.; Yang, W.; Yin, M. On-off-on Switchable Sensor: A Fluorescent Spiropyran Responds to Extreme pH Conditions and Its Bioimaging Applications ACS Appl. Mater. Interfaces 2014, 6, 19515-19519
18. 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
19. Snee, P. T.; Somers, R. C.; Nair, G.; Zimmer, J. P.; Bawendi, M. G.; Nocera, D. G. A Ratiometric CdSe/ZnS Nanocrystal pH Sensor J. Am. Chem. Soc. 2006, 128, 13320-13321
20. Hu, X.; Gao, X. Silica-Polymer Dual Layer-Encapsulated Quantum Dots with Remarkable Stability ACS Nano 2010, 4, 6080-6086
21. Zhang, R.; Zhao, D.; Ding, H.-G.; Huang, Y.-X.; Zhong, H.-Z.; Xie, H.-Y. Sensitive Single-Color Fluorescence off-on Switch System for dsDNA Detection Based on Quantum Dots-Ruthenium Assembling Dyads Biosens. Bioelectron. 2014, 56, 51-57
22. Wencel, D.; MacCraith, B. D.; McDonagh, C. High Performance Optical Ratiometric Sol-Gel-Based pH Sensor Sens. Actuators, B 2009, 139, 208-213
23. Peng, H.-S.; Stolwijk, J. A.; Sun, L.-N.; Wegener, J.; Wolfbeis, O. S. A Nanogel for Ratiometric Fluorescent Sensing of Intracellular pH Values Angew. Chem., Int. Ed. 2010, 122, 4342-4345
24. Wang, X.-D.; Stolwijk, J. A.; Lang, T.; Sperber, M.; Meier, R. J.; Wegener, J.; Wolfbeis, O. S. Ultra-Small, Highly Stable, and Sensitive Dual Nanosensors for Imaging Intracellular Oxygen and pH in Cytosol J. Am. Chem. Soc. 2012, 134, 17011-17014
25. Sun, G.; Cui, H.; Lin, L. Y.; Lee, N. S.; Yang, C.; Neumann, W. L.; Freskos, J. N.; Shieh, J. J.; Dorshow, R. B.; Wooley, K. L. Multicompartment Polymer Nanostructures with Ratiometric Dual-Emission pH-Sensitivity J. Am. Chem. Soc. 2011, 133, 8534-8543
26. Zhang, X.; Rehm, S.; Safont-Sempere, M. M.; Würthner, F. Vesicular Perylene Dye Nanocapsules as Supramolecular Fluorescent pH Sensor Systems Nat. Chem. 2009, 1, 623-629
27. 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
28. Kumar, E. K. P.; Almdal, K.; Andresen, T. L. Synthesis and Characterization of Ratiometric Nanosensors for pH Quantification: A Mixed Micelle Approach Chem. Commun. 2012, 48, 4776-4778
29. Lee, N. S.; Sun, G.; Lin, L. Y.; Neumann, W. L.; Freskos, J. N.; Karwa, A.; Shieh, J. J.; Dorshow, R. B.; Wooley, K. L. Tunable Dual-Emitting Shell-Crosslinked Nano-Objects as Single-Component Ratiometric pH-Sensing Materials J. Mater. Chem. 2011, 21, 14193-14202
30. Koopmans, C.; Ritter, H. Color Change of N-Isopropylacrylamide Copolymer Bearing Reichardts Dye as Optical Sensor for Lower Critical Solution Temperature and for Host-Guest Interaction with-Cyclodextrin J. Am. Chem. Soc. 2007, 129, 3502-3503
31. Wan, X.; Liu, S. Fluorescent Water-Soluble Responsive Polymers Site-Specifically Labeled with FRET Dyes Possessing pH- and Thermo-Modulated Multicolor Fluorescence Emissions as Dual Ratiometric Probes J. Mater. Chem. 2011, 21, 10321-10329
32. Wang, M.; Zou, S.; Guerin, G.; Shen, L.; Deng, K.; Jones, M.; Walker, G. C.; Scholes, G. D.; Winnik, M. A. A Water-Soluble pH-Responsive Molecular Brush of Poly(N, N -dimethylaminoethyl methacrylate) Grafted Polythiophene Macromolecules 2008, 41, 6993-7002
33. Thomas, S. W., III; Joly, G. D.; Swager, T. M. Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers Chem. Rev. 2007, 107, 1339-1386
34. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Conjugated Polymer-Based Chemical Sensors Chem. Rev. 2000, 100, 2537-2574
35. Jiang, H.; Taranekar, P.; Reynolds, J. R.; Schanze, K. S. Conjugated Polyelectrolytes: Synthesis, Photophysics, and Applications Angew. Chem., Int. Ed. 2009, 48, 4300-4316
36. Xu, Q.; An, L.; Yu, M.; Wang, S. Design and Synthesis of a New Conjugated Polyelectrolyte as a Reversible pH Sensor Macromol. Rapid Commun. 2008, 29, 390-395
37. Rugen-Penkalla, N.; Klapper, M.; Müllen, K. Highly Charged Conjugated Polymers with Polyphenylene Backbones and Poly(acrylic acid) Side Chains Macromolecules 2012, 45, 2301-2311
38. Jo, S.; Kim, D.; Son, S.-H.; Kim, Y.; Lee, T. S. Conjugated Poly(fluorene-quinoxaline) for Fluorescence Imaging and Chemical Detection of Nerve Agents with Its Paper-Based Strip ACS Appl. Mater. Interfaces 2014, 6, 1330-1336
39. Kim, I.-B.; Phillips, R.; Bunz, U. H. F. Carboxylate Group Side-Chain Density Modulates the pH-Dependent Optical Properties of PPEs Macromolecules 2007, 40, 5290-5293
40. Wang, F.; Bazan, G. C. Aggregation-Mediated Optical Properties of pH-Responsive Anionic Conjugated Polyelectrolytes J. Am. Chem. Soc. 2006, 128, 15786-15792
41. Naumov, P.; Kochunnoonny, M. Spectral-Structural Effects of the Keto-Enol-Enolate and Phenol-Phenolate Equilibria of Oxyluciferin J. Am. Chem. Soc. 2010, 132, 11566-11579
42. 2+-Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor J. Am. Chem. Soc. 2010, 132, 601-610
43. Wen, Q.; Liu, L.; Yang, Q.; Lv, F.; Wang, S. Dopamine-Modified Cationic Conjugated Polymer as a New Platform for pH Sensing and Autophagy Imaging Adv. Funct. Mater. 2013, 23, 764-769
44. Yang, C.-C.; Tian, Y.; Chen, C.-Y.; Jen, A. K. -Y.; Chen, W.-C. A Novel Benzoxazole-Containing Poly(N -isopropylacrylamide) Copolymer as a Multifunctional Sensing Material Macromol. Rapid Commun. 2007, 28, 894-899
45. Reichardt, C. Solvatochromic Dyes as Solvent Polarity Indicators Chem. Rev. 1997, 94, 2319-2358
46. Roncali, Z. Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems Chem. Rev. 1997, 97, 173-205
47. Ahn, H.; Kim, S.; Kim, O.; Choi, I.; Lee, C.-H.; Shim, J. H.; Park, M. J. Blue-emitting Self-assembled Polymer Electrolytes for Fast, Sensitive, Label-free Detection of Cu(II)-ions in Aqueous Media ACS Nano 2013, 7, 6162-6169