Aggregation-induced emission enhancement in alkoxy-bridged binuclear rhenium(I) complexes: Application as sensor for explosives and interaction with microheterogeneous media

Journal of Physical Chemistry B

Volumn 117, Issue 46, 2013, Pages 14358-14366

  Sathish, Veerasamy ^a   Ramdass, Arumugam ^a   Lu, Zong Zhan ^b   Velayudham, Murugesan ^b   Thanasekaran, Pounraj ^b   Lu, Kuang Lieh ^b   Rajagopal, Seenivasan ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATION-INDUCED EMISSIONS; AGGREGATIONINDUCED EMISSION ENHANCEMENT (AIEE); CETYLTRIMETHYLAMMONIUM BROMIDE; MICRO-HETEROGENEOUS; NITROAROMATIC COMPOUND; PHOTOPHYSICAL PROPERTIES; TIME-RESOLVED SPECTROSCOPY; UV-VIS ABSORPTIONS;

CHLORINE COMPOUNDS; LASER SPECTROSCOPY; MICELLES; SENSORS; SODIUM DODECYL SULFATE;

RHENIUM COMPOUNDS;

CETRIMIDE; COORDINATION COMPOUND; DICHLOROMETHANE; DODECYL SULFATE SODIUM; EXPLOSIVE; HEXANE; MACROGOL DERIVATIVE; POLYETHYLENE GLYCOL MONOOCTYLPHENYL ETHER; RHENIUM; WATER;

ARTICLE; CHEMISTRY; MICELLE; ULTRAVIOLET SPECTROPHOTOMETRY;

CETRIMONIUM COMPOUNDS; COORDINATION COMPLEXES; EXPLOSIVE AGENTS; HEXANES; METHYLENE CHLORIDE; MICELLES; POLYETHYLENE GLYCOLS; RHENIUM; SODIUM DODECYL SULFATE; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 84888613807     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp407939j     Document Type: Article

References (74)

1. Kumar, A.; Sun, S. S.; Lees, A. J. Directed Assembly Metallocyclic Supramolecular Systems for Molecular Recognition and Chemical Sensing Coord. Chem. Rev. 2008, 252, 922-939
2. Kuninobu, Y.; Takai, K. Organic Reactions Catalyzed by Rhenium Carbonyl Complexes Chem. Rev. 2011, 111, 1938-1953
3. Mauro, M.; Yang, C. H.; Shin, C. Y.; Panigati, M.; Chang, C. H.; D'Alfonso, G.; De Cola, L. Phosphorescent Organic Light-Emitting Diodes with Outstanding External Quantum Efficiency Using Dinuclear Rhenium Complexes as Dopants Adv. Mater. 2012, 24, 2054-2058
4. Lin, J. L.; Chen, C. W.; Sun, S. S.; Lees, A. J. Photoswitching Tetranuclear Rhenium(I) Tricarbonyl Diimine Complexes with a Stilbene-like Bridging Ligand Chem. Commun. 2011, 47, 6030-6032
5. Lo, K. K.-W.; Choi, A. W.-T.; Law, W. H.-T. Applications as Luminescent Inorganic and Organometallic Transition Metal Complexes as Biomolecular and Cellular probes Dalton Trans. 2012, 41, 6021-6047
6. 3Cl Chem. Commun. 2012, 48, 7374-7376
7. Balasingham, R. G.; Greenwood, F. L. T.; Williams, C. F.; Coogan, M. P.; Pope, S. J. A. Biologically Compatible, Phosphorescent Dimetallic Rhenium Complexes Linked through Functionalized Alkyl Chains: Syntheses, Spectroscopic Properties, and Applications in Imaging Microscopy Inorg. Chem. 2012, 51, 1419-1426
8. Balzani, V.; Scandola, F., Eds.; Supramolecular Photochemistry; Ellis Horwood: Chichester, UK, 1991.
9. Wang, C.; Wang, Z.; Zhang, X. Amphiphilic Building Blocks for Self-Assembly: From Amphiphiles to Supra-amphiphiles Acc. Chem. Res. 2012, 45, 608-618
10. 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
11. Manimaran, B.; Thanasekaran, P.; Rajendran, T.; Lin, R. J.; Chang, I. J.; Lee, G. H.; Peng, S. M.; Rajagopal, S.; Lu, K. L. Luminescence Enhancement Induced by Aggregation of Alkoxy-Bridged Rhenium(I) Molecular Rectangles Inorg. Chem. 2002, 41, 5323-5325
12. Tang, C. W.; Vanslyke, S. A. Organic Electroluminescent Diodes Appl. Phys. Lett. 1987, 51, 913-915
13. Suzuki, Y.; Yokoyama, K. Design and Synthesis of Intramolecular Charge Transfer-Based Fluorescent Reagents for the Highly-Sensitive Detection of Proteins J. Am. Chem. Soc. 2005, 127, 17799-17802
14. Zeng, Q.; Li, Z.; Dong, Y.; Di, C.; Qin, A.; Hong, Y.; Ji, L.; Zhu, Z.; Jim, C. K. W.; Yu, G.; Li, Q.; Li, Z.; Liu, Y.; Qin, J.; Tang, B. Z. Fluorescence Enhancements of Benzene-Cored Luminophors by Restricted Intramolecular Rotations: AIE and AIEE Effects Chem. Commun. 2007, 70-72
15. Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Aggregation-Induced Emission Chem. Soc. Rev. 2011, 40, 5361-5368
16. Zhao, Z.; Chen, S.; Chan, C. Y. K.; Lam, J. W. Y.; Jim, C. K. W.; Lu, P.; Chang, Z.; Kwok, H. S.; Qiu, H.; Tang, B. Z. A Facile and Versatile Approach to Efficient Luminescent Materials for Applications in Organic Light-Emitting Diodes Chem.-Asian J. 2012, 7, 484-488
17. Leung, C. W. T.; Hong, Y.; Chen, S.; Zhao, E.; Lam, J. W. Y.; Tang, B. Z. A Photostable AIE Luminogen for Specific Mitochondrial Imaging and Tracking J. Am. Chem. Soc. 2013, 135, 62-65
18. Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Bioprobes Based AIE Fluorogens. Acc. Chem. Res. DOI: 10.1021/ar3003464.
19. Hong, Y.; Meng, L.; Chen, S.; Leung, C. W. T.; Da, L. T.; Faisal, M.; Silva, D. A.; Liu, J.; Lam, J. W. Y.; Huang, X. Monitoring and Inhibition of Insulin Fibrillation by a Small Organic Fluorogen with Aggregation-Induced Emission Characteristics J. Am. Chem. Soc. 2012, 134, 1680-1684
20. Li, Y.; Xu, L.; Su, B. Aggregation Induced Emission for the Recognition of Latent Fingerprints Chem. Commun. 2012, 48, 4109-4111
21. Li, Z.; Dong, Y. Q.; Lam, J. W. Y.; Sun, J.; Qin, A.; Haußler, M.; Dong, Y. P.; Sung, H. H. Y.; Williams, I. D.; Kwok, H. S. Functionalized Siloles: Versatile Synthesis, Aggregation-Induced Emission, and Sensory and Device Applications Adv. Funct. Mater. 2009, 19, 905-917
22. 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
23. Xie, Z.; Yang, B.; Xie, W.; Liu, L.; Shen, F.; Wang, H.; Yang, X.; Wang, Z.; Li, Y.; Hanif, M. A Class of Nonplanar Conjugated Compounds with Aggregation-Induced Emission: Structural and Optical Properties of 2,5-Diphenyl-1,4-distyrylbenzene Derivatives with All Cis Double Bonds J. Phys. Chem. B 2006, 110, 20993-21000
24. Tong, H.; Dong, Y.; Hong, Y.; Haussler, M.; Lam, J. W. Y.; Sung, H. H.-Y.; Yu, X.; Sun, J.; Williams, I. D.; Kwok, H. S. Aggregation-Induced Emission: Effects of Molecular Structure, Solid-State Conformation, and Morphological Packing Arrangement on Light-Emitting Behaviors of Diphenyldibenzofulvene Derivatives J. Phys. Chem. C 2007, 111, 2287-2294
25. Deans, R.; Kim, J.; Machacek, M. R.; Swager, T. M. A Poly(p- phenyleneethynylene) with a Highly Emissive Aggregated Phase J. Am. Chem. Soc. 2000, 122, 8565-8566
26. Shustova, N. B.; McCarthy, B. D.; Dinca, M. Turn-On Fluorescence in Tetraphenylethylene-Based Metal-Organic Frameworks: An Alternative to Aggregation-Induced Emission J. Am. Chem. Soc. 2011, 133, 20126-20129
27. Procopio, E. Q.; Mauro, M.; Panigati, M.; Donghi, D.; Mercandelli, P.; Sironi, A.; D'Alfonso, G.; Decola, L. Highly Emitting Concomitant Polymorphic Crystals of a Dinuclear Rhenium Complex J. Am. Chem. Soc. 2010, 132, 14397-14399
28. Thanasekaran, P.; Lee, C. C.; Lu, K. L. One-Step Orthogonal-Bonding Approach to the Self-Assembly of Neutral Rhenium-Based Metallacycles: Synthesis, Structures, Photophysics, and Sensing Applications Acc. Chem. Res. 2012, 45, 1403
29. Thanasekaran, P.; Wu, J. Y.; Manimaran, B.; Rajendran, T.; Chang, I. J.; Rajagopal, S.; Lee, G. H.; Peng, S. M.; Lu, K. L. Aggregate of Alkoxy-Bridged Re(I)-Rectangles as a Probe for Photoluminescence Quenching J. Phys. Chem. A 2007, 111, 10953-10960
30. Sathish, V.; Babu, E.; Ramdass, A.; Lu, Z.-Z.; Chang, T. T.; Velayudham, M.; Thanasekaran, P.; Lu, K. L.; Li, W. S.; Rajagopal, S. Photoswitchable Alkoxy-Bridged Binuclear Rhenium(I) Complexes-A Potential Probe for Biomolecules and Optical Cell Imaging RSC Adv. 2013, 3, 18557-18566
31. Gupta, C.; Daechsel, A. K.; Chauhan, A. Interaction of Ionic Surfactants with Cornea-Mimicking Anionic Liposomes. Interaction of Ionic Surfactants with Cornea-Mimicking Anionic Liposomes Langmuir 2011, 27, 10840-10847
32. Kim, W.; Xiao, J.; Chaikof, E. L. Recombinant Amphiphilic Protein Micelles for Drug Delivery Langmuir 2011, 27, 14329-14334
33. Yin, J.-F.; Velayudham, M.; Bhattacharya, D.; Lin, H.-C.; Lu, K.-L. Structure Optimization of Ruthenium Photosensitizers for Efficient Dye-Sensitized Solar Cells-A Goal Toward a "Bright" Future Coord. Chem. Rev. 2012, 256, 3008-3035
34. Mandal, S.; Rao, V. G.; Ghatak, C.; Pramanik, R.; Sarkar, S.; Sarkar, N. Photophysics and Photodynamics of 1′-Hydroxy-2′-acetonaphthone (HAN) in Micelles and Nonionic Surfactants Forming Vesicles: a Comparative Study of Different Microenvironments of Surfactant Assemblies J. Phys. Chem. B 2011, 115, 12108-12119
35. Mahata, A.; Sarkar, D.; Bose, D.; Ghosh, D.; Girigoswami, A.; Das, P.; Chattopadhyay, N. Photophysics and Rotational Dynamics of a Carboline Analogue in Nonionic Micelles: Effect of Variation of Length of the Headgroup and the Tail of the Surfactant J. Phys. Chem. B 2009, 113, 7517-7526
36. Li, M.; Chen, Z.; Yam, V. W. W.; Zu, Y. Multifunctional Ruthenium(II) Polypyridine Complex-Based Core-Shell Magnetic Silica Nanocomposites: Magnetism, Luminescence, and Electrochemiluminescence ACS Nano 2008, 2, 905-912
37. Martinez, A. G.; Vida, Y.; Gutierrez, D. D.; Albuquerque, R. Q.; De Cola, L. Tuning Emission Properties of Iridium and Ruthenium Metallosurfactants in Micellar Systems Inorg. Chem. 2008, 47, 9131-9133
38. Dressick, W. J.; Cline, J.; Demas, J. N.; DeGraff, B. A. Energy Degradation Pathways and Binding Site Environment of Micelle Bound Ruthenium(II) Photosensitizers J. Am. Chem. Soc. 1986, 108, 7567-7574
39. Hauenstein, B. L.; Dressick, W. J.; Gilbert, T. B.; Demas, J. N.; DeGraff, B. A. Interactions of Ruthenium(II) Photosensitizers with Non-Ionic Surfactants: The Binding Region and Specific-Anion Effects J. Phys. Chem. 1984, 88, 1902-1905
40. 99mTc, Re) Chem. Commun. 2012, 48, 4211-4213
41. Yam, V. W. W.; Lau, V. C. Y.; Wang, K. Z.; Cheunga, K. K.; Huang, C. H. Synthesis, Photophysics, Photochemistry, Electrochemistry and Structural Studies of Luminescent Rhenium(I) Surfactant Complexes; Non-linear Optical Properties in Langmuir-Blodgett Films J. Mater. Chem. 1998, 8, 89-97
42. Wang, H. Y.; Wang, W. G.; Si, G.; Wang, F.; Tung, C. H.; Wu, L. Z. Photocatalytic Hydrogen Evolution from Rhenium(I) Complexes to [FeFe] Hydrogenase Mimics in Aqueous SDS Micellar Systems: A Biomimetic Pathway Langmuir 2010, 26, 9766-9771
43. Crosby, G. A.; Demas, J. N. Measurement of Photoluminescence Quantum Yields. Review J. Phys. Chem. 1971, 75, 991
44. Chien, R. H.; Lai, C. T.; Hong, J. L. Hydrogen Bonds and Enhanced Aggregation Emission of Organic and Polymeric Fluorophores with Alternative Fluorene and Naphthol Units J. Phys. Chem. C 2011, 115, 12358-12366
45. 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
46. Karukstis, K. K.; Perelman, L. A.; Wong, W. K. Spectroscopic Characterization of Azo Dye Aggregation on Dendrimer Surfaces Langmuir 2002, 18, 10363-10371
47. Whitten, D. G.; Chen, L.; Geiger, H. C.; Perlstein, J.; Song, X. Self-Assembly of Aromatic-Functionalized Amphiphiles: The Role and Consequences of Aromatic-Aromatic Noncovalent Interactions in Building Supramolecular Aggregates and Novel Assemblies J. Phys. Chem. B 1998, 102, 10098-10111
48. Wang, F.; Wen, J.; Huang, L.; Huang, J.; Ouyang, J. A Highly Sensitive "Switch-On" Fluorescent Probe for Protein Quantification and Visualization Based on Aggregation-Induced Emission Chem. Commun. 2012, 48, 7395-7397
49. Feng, X.; Tong, B.; Shen, J.; Shi, J.; Han, T.; Chen, L.; Zhi, J.; Lu, P.; Ma, Y.; Dong, Y. Aggregation-Induced Emission Enhancement of Aryl-Substituted Pyrrole Derivatives J. Phys. Chem. B 2010, 114, 16731-16736
50. Han, Q.; Su, Q.; Tang, L.; Feng, J.; Lu, P.; Wang, Y. Electron Transfer and Aggregate Formation Coinduced Emission Enhancement of 9- Cycloheptatrienylidene Fluorenes in the Presence of Cupric Chloride J. Phys. Chem. C 2010, 114, 18702-18711
51. Qian, Y.; Li, S.; Zhang, G.; Wang, Q.; Wang, S.; Xu, H.; Li, C.; Li, Y.; Yang, G. Aggregation-Induced Emission Enhancement of 2-(2′-Hydroxyphenyl) benzothiazole-Based Excited-State Intramolecular Proton-Transfer Compounds J. Phys. Chem. B 2007, 111, 5861-5868
52. Donghi, D.; Maggioni, D.; D'Alfonso, G.; Amigoni, F.; Ranucci, E.; Ferruti, P.; Manfredi, A.; Fenili, F.; Bisazza, A.; Cavalli, R. Tricarbonyl-Rhenium Complexes of a Thiol-Functionalized Amphoteric Poly(amidoamine) Biomacromolecules 2009, 10, 3273-3282
53. + Pendants Bonded to Poly(4-vinylpyridine) J. Phys. Chem. B 2008, 112, 11506-11516
54. Salinas, Y.; Manez, R. M.; Marcos, M. D.; Sancenon, F.; Costero, A. M.; Parra, M.; Gil, S. Optical Chemosensors and Reagents to Detect Explosives Chem. Soc. Rev. 2012, 41, 1261-1296
55. Lai, C.-Y.; Trewyn, B. G.; Jeftinija, D. M.; Jeftinija, K.; Xu, S.; Jeftinija, S.; Lin, V. S.-Y. A Mesoporous Silica Nanosphere-Based Carrier System with Chemically Removable CdS Nanoparticle Caps for Stimuli-Responsive Controlled Release of Neurotransmitters and Drug Molecules J. Am. Chem. Soc. 2003, 125, 4451-4459
56. Toal, S. J.; Trogler, W. C. Polymer Sensors for Nitroaromatic Explosives Detection J. Mater. Chem. 2006, 16, 2871-2883
57. Wang, X.; Guo, Y.; Li, D.; Chen, H.; Sun, R.-C. Fluorescent Amphiphilic Cellulose Nanoaggregates for Sensing Trace Explosives in Aqueous Solution Chem. Commun. 2012, 48, 5569-5571
58. Pandya, A.; Goswami, H.; Lodhaband, A.; Menon, S. K. A Novel Nanoaggregation Detection Technique of TNT Using Selective and Ultrasensitive Nanocurcumin as a Probe Analyst 2012, 137, 1771-1774
59. Bhalla, V.; Gupta, A.; Kumar, M. Fluorescent Nanoaggregates of Pentacenequinone Derivative for Selective Sensing of Picric Acid in Aqueous Media Org. Lett. 2012, 14, 3112-3115
60. Li, D.; Liu, J.; Kwok, R. T. K.; Liang, Z.; Tang, B. Z.; Yu, J. Supersensitive Detection of Explosives by Recyclable AIE Luminogen- Functionalized Mesoporous Materials Chem. Commun. 2012, 48, 7167-7169
61. Wang, J.; Mei, J.; Yuan, W.; Lu, P.; Qin, A.; Sun, J.; Ma, Y.; Tang, B. Z. Hyperbranched Polytriazoles with High Molecular Compressibility: Aggregation-Induced Emission and Superamplified Explosive Detection J. Mater. Chem. 2011, 21, 4056-4059
62. Shanmugaraju, S.; Joshi, S. A.; Mukherjee, P. S. Self-Assembly of Metallamacrocycles Using a Dinuclear Organometallic Acceptor: Synthesis, Characterization, and Sensing Study Inorg. Chem. 2011, 50, 11736-11745
63. Saroja, G.; Ramachandram, B.; Saha, S.; Samanta, A. The Fluorescence Response of a Structurally Modified 4-Aminophthalimide Derivative Covalently Attached to a Fatty Acid in Homogeneous and Micellar Environments J. Phys. Chem. B 1999, 103, 2906-2911
64. Rajendran, T.; Rajagopal, S.; Srinivasan, C.; Ramamurthy, P. Micellar Effect on the Photoinduced Electron-Transfer Reactions of Ruthenium(II)- Polypyridyl Complexes with Phenolate Ions. Effect of Cetyltrimethylammoniumchloride J. Chem. Soc., Faraday Trans. 1997, 93, 3155-3160
65. Rainò, G.; Stöferle, T.; Park, C.; Kim, H.-C.; Chin, I.-J.; Miller, R. D.; Mahrt, R. F. Dye Molecules Encapsulated in a Micelle Structure: Nano-Aggregates with Enhanced Optical Properties Adv. Mater. 2010, 22, 3681-3684
66. Almgren, M.; Grieser, F.; Thomas, J. K. Dynamic and Static Aspects of Solubilization of Neutral Arenes in Ionic Micellar Solutions J. Am. Chem. Soc. 1979, 101, 279-291
67. Kumbhakar, M.; Singh, P. K.; Nath, S.; Bhasikuttan, A. C.; Pal, H. Ultrafast Bimolecular Electron Transfer Dynamics in Micellar Media J. Phys. Chem. B 2008, 112, 6646-6652
68. Wang, X.; Kofron, W. G.; Kong, S.; Rajesh, C. S.; Modarelli, D. A.; Lim, E. C. Transient Absorption Probe of Intermolecular Triplet Excimer of Naphthalene in Fluid Solutions: Identification of the Species Based on Comparison to the Intramolecular Triplet Excimers of Covalently-Linked Dimers J. Phys. Chem. A 2000, 104, 1461-1465
69. Correa, N. M.; Silber, J. J.; Riter, R. E.; Levinger, N. E. Nonaqueous Polar Solvents in Reverse Micelle Systems Chem. Rev. 2012, 112, 4569-4602
70. Setua, P.; Ghatak, C.; Rao, V. G.; Das, S. K.; Sarkar, N. Dynamics of Solvation and Rotational Relaxation of Coumarin 480 in Pure Aqueous-AOT Reverse Micelle and Reverse Micelle Containing Different-Sized Silver Nanoparticles Inside Its Core: A Comparative Study J. Phys. Chem. B 2012, 116, 3704-3712
71. Yeung, P. S.-W.; Axelsen, P. H. The Crowded Environment of a Reverse Micelle Induces the Formation of β-Strand Seed Structures for Nucleating Amyloid Fibril Formation J. Am. Chem. Soc. 2012, 134, 6061-6063
72. Re→bpy Luminescence by Cu(II) Species in Re(I) Polymer Micelles J. Phys. Chem. B 2005, 109, 22890-22898
73. Hou, S.; Man, K. Y. K.; Chan, W. K. Nanosized Micelles Formed by the Self-assembly of Amphiphilic Block Copolymers with Luminescent Rhenium Complexes Langmuir 2003, 19, 2485-2490
74. 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 Technology