Spiropyran polymeric microcapillary coatings for photodetection of solvent polarity

Langmuir

Volumn 29, Issue 8, 2013, Pages 2790-2797

  Florea, Larisa ^a   McKeon, Aoife ^a   Diamond, Dermot ^a   Benito Lopez, Fernando ^a,b  

^a DUBLIN CITY UNIVERSITY   (Ireland)

^b CIC MICROGUNE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CONTINUOUS FLOWS; DIFFERENT SOLVENTS; FUNCTIONALIZED; MEROCYANINE; MICRO-CAPILLARIES; PHOTO DETECTION; RING OPENING; RING OPENING METATHESIS POLYMERIZATION; SOLVENT POLARITY; SPECTRAL RESPONSE; SPIROPYRAN MOIETY; SPIROPYRANS; SURFACE-INITIATED; TETRA-HYDROFURAN;

ACETONE; ACETONITRILE; ETHANOL; METHANOL; PHOTOCHROMISM; PLASTIC COATINGS; POLYMERS; RING OPENING POLYMERIZATION; SOLVENTS; TOLUENE;

ORGANIC SOLVENTS;

BENZOPYRAN DERIVATIVE; INDOLE DERIVATIVE; NITRO DERIVATIVE; POLYMER; SOLVENT; SPIROPYRAN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PARTICLE SIZE; PHOTOCHEMISTRY; SURFACE PROPERTY; SYNTHESIS; ULTRAVIOLET RADIATION;

BENZOPYRANS; INDOLES; MOLECULAR STRUCTURE; NITRO COMPOUNDS; PARTICLE SIZE; PHOTOCHEMICAL PROCESSES; POLYMERS; SOLVENTS; SURFACE PROPERTIES; ULTRAVIOLET RAYS;

EID: 84874427113     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la304985p     Document Type: Article

References (46)

1. Weigl, B. H.; Wolfbeis, O. S. Capillary optical sensors Anal. Chem. 1994, 66 (20) 3323-3327
2. Kuswandi, B.; Narayanaswamy, R. Capillary optode: Determination of mercury(II) in aqueous solution Anal. Lett. 1999, 32 (4) 649-664
3. Kuswandi, B.; Narayanaswamy, R. Polymeric encapsulated membrane for optrodes Fresenius J. Anal. Chem. 1999, 364 (6) 605-607
4. Buchholz, F.; Buschmann, N.; Cammann, K. A fiberoptic sensor for the determination of sodium with a reversible response Sens. Actuators, B 1992, 9 (1) 41-47
5. Fischer, E.; Hirshberg, Y. Formation of coloured forms of spirans by low-temperature irradiation J. Chem. Soc. 1952, 868, 4522-4524
6. Zhu, M. Q.; Zhu, L. Y.; Han, J. J.; Wu, W. W.; Hurst, J. K.; Li, A. D. Q. Spiropyran-based photochromic polymer nanoparticles with optically switchable luminescence J. Am. Chem. Soc. 2006, 128 (13) 4303-4309
7. Minkin, V. I. Photo-, thermo-, solvato-, and electrochromic spiroheterocyclic compounds Chem. Rev. 2004, 104 (5) 2751-2776
8. Uchida, K.; Takata, A.; Saito, M.; Murakami, A.; Nakamura, S.; Irie, M. A novel photochromic film by oxidation polymerization of a bisbenzothienylethene with phenol groups Adv. Mater. 2003, 15 (10) 785-788
9. Zhang, Y.; Shao, N.; Yang, R.; Li, K. a.; Liu, F.; Chan, W.; Mo, T. Utilization of a spiropyran derivative in a polymeric film optode for selective fluorescent sensing of zinc ion Sci. Chin., Ser. B 2006, 49 (3) 246-255
10. Ma, Y.; Niu, C.; Wen, Y.; Li, G.; Wang, J.; Li, H.; Du, S.; Yang, L.; Gao, H.; Song, Y. Stable and reversible optoelectrical dual-mode data storage based on a ferrocenlylspiropyran molecule Appl. Phys. Lett. 2009, 95 (18) 183307
11. Vollmer, H. P. Investigations on quantum yield and stability of coloration of uv-sensitive spiropyran layers used as a recording material for optical data storage Z. Naturforsch., A: Phys. Sci. 1975, 30 (11) 1425-1432
12. Bobrovsky, A. Y.; Boiko, N. I.; Shibaev, V. P. Photosensitive cholesteric copolymers with spiropyran-containing side groups: Novel materials for optical data recording Adv. Mater. 1999, 11 (12) 1025-1028
13. Jiang, G.; Song, Y.; Guo, X.; Zhang, D.; Zhu, D. Organic functional molecules towards information processing and high-density information storage Adv. Mater. 2008, 20 (15) 2888-2898
14. Tian, H.; Feng, Y. Next step of photochromic switches? J. Mater. Chem. 2008, 18 (14) 1617-1622
15. Hirshberg, Y. Reversible formation and eradication of colors by irradiation at low temperatures-a photochemical memory model J. Am. Chem. Soc. 1956, 78 (10) 2304-2312
16. Berkovic, G.; Krongauz, V.; Weiss, V. Spiropyrans and spirooxazines for memories and switches Chem. Rev. 2000, 100 (5) 1741-1753
17. Preigh, M. J.; Stauffer, M. T.; Lin, F. T.; Weber, S. G. Anodic oxidation mechanism of a spiropyran J. Chem. Soc., Faraday Trans. 1996, 92 (20) 3991-3996
18. Zhu, J.-F.; Yuan, H.; Chan, W.-H.; Lee, A. W. M. A colorimetric and fluorescent turn-on chemosensor operative in aqueous media for Zn(2+) based on a multifunctionalized spirobenzopyran derivative Org. Biomol. Chem. 2010, 8 (17) 3957-3964
19. Rosario, R.; Gust, D.; Hayes, M.; Jahnke, F.; Springer, J.; Garcia, A. A. Photon-modulated wettability changes on spiropyran-coated surfaces Langmuir 2002, 18 (21) 8062-8069
20. Benito-Lopez, F.; Scarmagnani, S.; Walsh, Z.; Paull, B.; Macka, M.; Diamond, D. Spiropyran modified micro-fluidic chip channels as photonically controlled self-indicating system for metal ion accumulation and release Sens. Actuators, B 2009, 140 (1) 295-303
21. Keum, S. R.; Hur, M. S.; Kazmaier, P. M.; Buncel, E. Thermochromic and photochromic dyes-indolino-benzospiropyrans 0.1. uv-vis spectroscopic studies of 1,3,3-spiro(2H-1-benzopyran-2,2′-indolines) and the open-chain merocyanine forms-solvatochromism and medium effects on spiro ring formation Can. J. Chem. 1991, 69 (12) 1940-1947
22. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 4 th ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2010.
23. Murugan, N. A.; Chakrabarti, S.; Agren, H. Solvent Dependence of Structure, Charge Distribution, and Absorption Spectrum in the Photochromic Merocyanine-Spiropyran Pair J. Phys. Chem. B 2011, 115 (14) 4025-4032
24. Botrel, A.; Aboab, B.; Corre, F.; Tonnard, F. A theoretical investigation of solvatochromism-application to merocyanines similar to colored forms obtained by flash-photolysis of spiropyrans Chem. Phys. 1995, 194 (1) 101-116
25. Shirinian, V. Z.; Besugliy, S. O.; Metelitsa, A. V.; Krayushkin, M. M.; Nikalin, D. M.; Minkin, V. I. Novel photochromic spirocyclic compounds of thienopyrroline series: 1 Spiropyrans J. Photochem. Photobiol., A 2007, 189 (2-3) 161-166
26. Keum, S.-R.; Roh, S.-J.; Ahn, S.-M.; Lim, S.-S.; Kim, S.-H.; Koh, K. Solvatochromic behavior of non-activated indolinobenzospiropyran 6-carboxylates in aqueous binary solvent mixtures. Part II Dyes Pigm. 2007, 74 (2) 343-347
27. Byrne, R.; Coleman, S.; Gallagher, S.; Diamond, D. Designer molecular probes for phosphonium ionic liquids Phys. Chem. Chem. Phys. 2010, 12 (8) 1895-1904
28. Byrne, R.; Coleman, S.; Fraser, K. J.; Raduta, A.; MacFarlane, D. R.; Diamond, D. Photochromism of nitrobenzospiropyran in phosphonium based ionic liquids Phys. Chem. Chem. Phys. 2009, 11 (33) 7286-7291
29. Rosario, R.; Gust, D.; Hayes, M.; Springer, J.; Garcia, A. A. Solvatochromic study of the microenvironment of surface-bound spiropyrans Langmuir 2003, 19 (21) 8801-8806
30. Bosch Ojeda, C.; Sanchez Rojas, F. Recent development in optical chemical sensors coupling with flow injection analysis Sensors 2006, 6 (10) 1245-1307
31. Florea, L.; Diamond, D.; Benito-Lopez, F. Polyaniline Coated Micro-capillaries for Continuous Flow Analysis of Aqueous Solutions Anal. Chim. Acta 2012, http://dx.doi.org/10.1016/j.aca.2012.11.027
32. Gonzalez-de los Santos, E. A.; Lozano-Gonzalez, M. J.; Johnson, A. F. Photoresponsive polyurethane-acrylate block copolymers. I. Photochromic effects in copolymers containing 6 ′-nitro spiropyranes and 6 ′-nitro-bis- spiropyranes J. Appl. Polym. Sci. 1999, 71 (2) 259-266
33. Marsella, M. J.; Wang, Z. Q.; Mitchell, R. H. Backbone photochromic polymers containing the dimethyldihydropyrene moiety: Toward optoelectronic switches Org. Lett. 2000, 2 (19) 2979-2982
34. Guo, X. F.; Zhang, D.; Gui, Y.; Wax, M. X.; Li, J. C.; Liu, Y. Q.; Zhu, D. B. Reversible photoregulation of the electrical conductivity of spiropyran-doped polyaniline for information recording and nondestructive processing Adv. Mater. 2004, 16 (7) 636-640
35. Keum, S.-R.; Ahn, S.-M.; Roh, S.-J.; Ma, S.-Y. The synthesis and spectroscopic properties of novel, photochromic indolinobenzospiropyran-based homopolymers prepared via ring-opening metathesis polymerization Dyes Pigm. 2010, 86 (1) 74-80
36. Florea, L.; Hennart, A.; Diamond, D.; Benito-Lopez, F. Synthesis and characterisation of spiropyran-polymer brushes in micro-capillaries: Towards an integrated optical sensor for continuous flow analysis Sens. Actuators B: Chem. 2012, 175, 92-99
37. Samanta, S.; Locklin, J. Formation of photochromic spiropyran polymer brushes via surface-initiated, ring-opening metathesis polymerization: Reversible photocontrol of wetting behavior and solvent dependent morphology changes Langmuir 2008, 24 (17) 9558-9565
38. Rule, J. D.; Moore, J. S. ROMP reactivity of endo- and exo-dicyclopentadiene Macromolecules 2002, 35 (21) 7878-7882
39. Zhou, J. W.; Li, Y. T.; Tang, Y. W.; Zhao, F. Q.; Song, X. Q.; Li, E. C. Detailed investigation on a negative photochromic spiropyran J. Photochem. Photobiol., A 1995, 90 (2-3) 117-123
40. Song, X. Q.; Zhou, J. W.; Li, Y. T.; Tang, Y. W. Correlations between solvatochromism, Lewis acid-base equilibrium and photochromism of an indoline spiropyran J. Photochem. Photobiol., A 1995, 92 (1-2) 99-103
41. Uznanski, P. UV-assisted formation of nanoaggregates from photochromic spiropyrans in nonpolar solvents Langmuir 2003, 19 (6) 1919-1922
42. Fries, K. H.; Driskell, J. D.; Samanta, S.; Locklin, J. Spectroscopic Analysis of Metal Ion Binding in Spiropyran Containing Copolymer Thin Films Anal. Chem. 2010, 82 (8) 3306-3314
43. Kong, B.; Lee, J. K.; Choi, I. S. Surface-Initiated, Ring-Opening Metathesis Polymerization: Formation of Diblock Copolymer Brushes and Solvent-Dependent Morphological Changes Langmuir 2007, 23 (10) 6761-6765
44. Byrne, L.; Barker, J.; Pennarun-Thomas, G.; Diamond, D.; Edwards, S. Digital imaging as a detector for generic analytical measurements Trends Anal. Chem. 2000, 19 (8) 517-522
45. Fay, C.; Lau, K.-T.; Beirne, S.; Conaire, C. O.; McGuinness, K.; Corcoran, B.; O'Connor, N. E.; Diamond, D.; McGovern, S.; Coleman, G.; Shepherd, R.; Alici, G.; Spinks, G.; Wallace, G. Wireless aquatic navigator for detection and analysis (WANDA) Sens. Actuators, B 2010, 150 (1) 425-435
46. Zanoni, M.; Coleman, S.; Fraser, K. J.; Byrne, R.; Wagner, K.; Gambhir, S.; Officer, D. L.; Wallace, G. G.; Diamond, D. Physicochemical study of spiropyran-terthiophene derivatives: photochemistry and thermodynamics Phys. Chem. Chem. Phys. 2012, 14 (25) 9112-9120