Synthesis of an amphiphilic rhodamine derivative and characterization of its solution and thin film properties

Thin Solid Films

Volumn 564, Issue , 2014, Pages 86-91

  Aviv, Hagit ^a,b   Harazi, Sivan ^a,b   Schiff, Dillon ^a,b   Ramon, Yoni ^a,b   Tischler, Yaakov R ^a,b  

^a BAR ILAN UNIVERSITY   (Israel)

^b Department of Physics Bar Ilan University ^*  (Israel)

Author keywords

Dopant; Dye; Langmuir Blodgett; Micelle; Monolayer; Photoluminescence

Indexed keywords

AGGLOMERATION; CHLORINE COMPOUNDS; DOPING (ADDITIVES); DYEING; MICELLES; MONOLAYERS; PHOTOLUMINESCENCE; THIN FILMS;

AIR WATER INTERFACES; FLUORESCENCE QUANTUM YIELD; LANGMUIR-BLODGETT; LANGMUIR-BLODGETT DEPOSITION; PHOTOLUMINESCENCE PEAK; SULFONYL CHLORIDES; SULFONYLATION REACTIONS; THIN-FILM PROPERTIES;

THIN FILM TRANSISTORS;

EID: 84904035116     PISSN: 00406090     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tsf.2014.05.009     Document Type: Article

References (47)

1. Y. Zhang, X.Y. Sun, and B. Liu Fluorescent recognition for single- and double-stranded oligonucleotides based on rhodamine B-modified self-assembled bilayers Chin. J. Anal. Chem. 37 2009 665
2. Z.Q. Hu, M. Li, M.D. Liu, W.M. Zhuang, and G.K. Li A highly sensitive fluorescent acidic pH probe based on rhodamine B diethyl-2-aminobutenedioate conjugate and its application in living cells Dyes Pigments 96 2013 71
3. M.N. Slyadnev, T. Inoue, A. Harata, and T. Ogawa A rhodamine and a cyanine dye on the water surface as studied by laser induced fluorescence microscopy Colloid Surf. A 164 2000 155
4. Y. Gao, J.L. Li, and Z. Shi Synthesis and application of rhodamine-based fluorescent probe dyes with spacer linker arm Chin. Chem. Lett. 18 2007 667
5. J.H. Werner, H. Cai, J.H. Jett, L. Reha-Krantz, R.A. Keller, and P.M. Goodwin Progress towards single-molecule DNA sequencing: a one color demonstration J. Biotechnol. 102 2003 1
6. F. Liu, B. Sanyasi Rao, and J.-M. Nunzi A novel dye functionalized silver-silica core-shell NPs and its application in organic light emitting diodes Org. Electron. 12 2011 1279
7. S. Yang, F. Meng, H. Tian, and K. Chen Photostability of novel copolymers functionalized with laser dyes based on modified rhodamine 6G and 1,8-naphthalimide Eur. Polym. J. 38 2002 911
8. X.L. Zhu, L. Shi, J. Chan, J. Wang, C. Ye, and D. Lo Optical properties of zirconia-titania-ORMOSIL films for temperature tuning distributed feedback waveguide lasers Opt. Commun. 251 2005 322
9. M.B. Ahamed, A. Ramalingam, and P.K. Palanisamy Studies on widely tunable ultra-short laser pulses using energy transfer distributed feedback dye laser J. Lumin. 105 2003 9
10. M. Basheer Ahamed, and P.K. Palanisamy Nd:YAG laser pumped energy transfer distributed feedback dye laser in Rhodamine 6G and Acid blue 7 dye mixture Opt. Commun. 213 2002 67
11. S.N. Smith, and R.P. Steer The photophysics of Lissamine rhodamine-B sulphonyl chloride in aqueous solution: implications for fluorescent protein-dye conjugates J. Photochem. Photobiol. A 139 2001 151
12. E. Vuorimaa, H. Lemmetyinen, M. Van der Auweraer, and F.C. De Schryver Photochemical processes in mixed Langmuir-Blodgett films of rhodamine B and anthracene Thin Solid Films 268 1995 114
13. K.-i. Ishibashi, O. Sato, R. Baba, D.A. Tryk, K. Hashimoto, and A. Fujishima Characterization of the chromophore orientation of rhodamine B amphiphiles in Langmuir-Blodgett monolayers J. Colloid Interface Sci. 233 2001 361
14. B.M. Castro, R.F.M. de Almeida, A. Fedorov, and M. Prieto The photophysics of a Rhodamine head labeled phospholipid in the identification and characterization of membrane lipid phases Chem. Phys. Lipids 165 2012 311
15. J. Yuan, C. Hao, M. Chen, P. Berini, and S. Zou Lipid reassembly in asymmetric Langmuir-Blodgett/Langmuir-Schaeffer bilayers Langmuir 29 2013 221
16. P.M. Keller, S. Person, and W. Snipes A fluorescence enhancement assay of cell fusion J. Cell Sci. 28 1977 167
17. M. Van der Auweraer, B. Verschuere, and F.C. De Schryver Absorption and fluorescence properties of rhodamine B derivatives forming Langmuir-Blodgett films Langmuir 4 1988 583
18. P. Ballet, M. Van der Auweraer, F.C. De Schryver, H. Lemmetyinen, and E. Vuorimaa Global analysis of the fluorescence decays of N, N′-dioctadecyl rhodamine B in Langmuir-Blodgett films of diacylphosphatidic acids J. Phys. Chem. 100 1996 13701
19. G. Biesmans, M. Van der Auweraer, C. Cathry, D. Meerschaut, F. De Schryver, W. Storck, and F. Willig Photosensitized electron injection from xanthene dyes incorporated in Langmuir-Blodgett films into tin dioxide electrodes J. Phys. Chem. 95 1991 3771
20. D. Pevenage, M. Van der Auweraer, and F.C. De Schryver Influence of the molecular structure on the lateral listribution of xanthene dyes in Langmuir-Blodgett films Langmuir 15 1999 8465
21. A.E. Bedrick, J.L. Painter, and D.L. Bonitz Spectral properties and relative quantum yields of new fluorescent stains Immunopharmacology 2 1979 33
22. K.G. Casey, Y. Onganer, and E.L. Quitevis Effect of solvent polarity on non-radiative processes in xanthene dyes: the acid form of rhodamine B in nitrile solvents J. Photochem. Photobiol. A 64 1992 307
23. M. Fikry, M.M. Omar, and L. Ismail Effect of host medium on the fluorescence emission intensity of rhodamine B in liquid and solid phase J. Fluoresc. 19 2009 741
24. A.M. Kartal, and C. Erkey Surface modification of silica aerogels by hexamethyldisilazane-carbon dioxide mixtures and their phase behavior J. Supercrit. Fluids 53 2010 115
25. D.K. Schwartz Langmuir-Blodgett film structure Surf. Sci. Rep. 27 1997 245
26. N.O. McHedlov-Petrossyan, N.A. Vodolazkaya, O.N. Bezkrovnaya, A.G. Yakubovskaya, A.V. Tolmachev, and A.V. Grigorovich Fluorescent dye N, N′-dioctadecylrhodamine as a new interfacial acid-base indicator Spectrochim. Acta A 69 2008 1125
27. Y. Wang, H. Wu, J. Luo, and X. Liu Synthesis of an amphiphilic copolymer bearing rhodamine moieties and its self-assembly into micelles as chemosensors for Fe3 + in aqueous solution React. Funct. Polym. 72 2012 169
28. S.C. Chang, S.J. Chiu, C.Y. Hsu, Y. Chang, and Y.L. Liu White-light fluorescent nanoparticles from self-assembly of rhodamine B-anchored amphiphilic poly(poly(ethylene glycol)methacrylate)-b-poly(glycidyl methacrylate) block copolymer Polymer 53 2012 4399
29. D.E. Bergeron Determination of micelle size in some commercial liquid scintillation cocktails Appl. Radiat. Isot. 70 2012 2164
30. S.A. Hussain, D. Dey, S. Chakraborty, and D. Bhattacharjee J-aggregates of thiacyanine dye organized in LB films: effect of irradiation of light J. Lumin. 131 2011 1655
31. K. Kemnitz, T. Murao, I. Yamazaki, N. Nakashima, and K. Yoshihara Picosecond fluorescence measurement of submono- and mono-layer of adsorbed rhodamine B on a single crystal of naphthalene and on glass Chem. Phys. Lett. 101 1983 337
32. K. Kemnitz, N. Tamai, I. Yamazaki, N. Nakashima, and K. Yoshihara Fluorescence decays and spectral properties of rhodamine B in submono-, mono-, and multilayer systems J. Phys. Chem. 90 1986 5094
33. K. Kemnitz, N. Tamai, I. Yamazaki, N. Nakashima, and K. Yoshihara Site-dependent fluorescence lifetimes of isolated dye molecules adsorbed on organic single crystals and other substrates J. Phys. Chem. 91 1987 1423
34. Y. Liang, and A.P. Goncalves Time-resolved measurements of the fluorescence of Rhodamine B on semiconductor and glass surfaces J. Phys. Chem. 89 1985 3290
35. Y. Liang, A. Ponte Goncalves, and D. Negus Picosecond fluorescence lifetime measurements on dyes adsorbed at semiconductor and insulator surfaces J. Phys. Chem. 87 1983 1
36. Y. Liang, P.F. Moy, J.A. Poole, and A.M. Ponte Goncalves Fluorescence of rhodamine B on semiconductor and insulator surfaces: dependence of the quantum yield on surface coverage J. Phys. Chem. 88 1984 2451
37. J. Catalán Toward a generalized treatment of the solvent effect based on four empirical scales: dipolarity (SdP, a new scale), polarizability (SP), acidity (SA), and basicity (SB) of the medium J. Phys. Chem. B 113 2009 5951
38. A. Filarowski, M. Kluba, K. Cieślik-Boczula, A. Koll, A. Kochel, L. Pandey, W.M. De Borggraeve, M. Van der Auweraer, J. Catalán, and N. Boens Generalized solvent scales as a tool for investigating solvent dependence of spectroscopic and kinetic parameters. Application to fluorescent BODIPY dyes Photochem. Photobiol. Sci. 9 2010 996
39. S.V. Shekhovtsov, N.O. McHedlov-Petrossyan, and C. Reichardt A new application of solvatochromic pyridinium-N-phenolate betaine dyes: examining the electrophilicity of lanthanide shift reagents Tetrahedron Lett. 51 2010 4347
40. L.G.S. Brooker, G.H. Keyes, and W.W. Williams Color and constitution. V. 1 The absorption of unsymmetrical cyanines. Resonance as a basis for a classification of dyes J. Am. Chem. Soc. 64 1942 199
41. L.G.S. Brooker, F.L. White, G.H. Keyes, C.P. Smyth, and P.F. Oesper Color and constitution. II.1 Absorptions of some related vinylene-homologous series J. Am. Chem. Soc. 63 1941 3192
42. H. Kuhn Elektronengasmodell zur quantitativen deutung der lichtabsorption von organischen farbstoffen II. teil B. störung des elektronengases durch heteroatome Helv. Chim. Acta 34 1951 2371
43. H. Kuhn, W. Huber, G. Handschig, H. Martin, F. Schäfer, and F. Bär Nature of the free electron model. The simple case of the symmetric polymethines J. Chem. Phys. 32 1960 467
44. R.G. Laughlin The basicity of aliphatic sulfonamides J. Am. Chem. Soc. 89 1967 4268
45. B. Tah, P. Pal, M. Mahato, and G.B. Talapatra Aggregation behavior of SDS/CTAB catanionic surfactant mixture in aqueous solution and at the air/water interface J. Phys. Chem. B 115 2011 8493
46. E.A. Meyer, R.K. Castellano, and F. Diederich Interactions with aromatic rings in chemical and biological recognition Angew. Chem. Int. Edit. 42 2003 1210
47. S.A. Yeroshina, N.K. Ibrayev, S.E. Kudaibergenov, F. Rullens, M. Devillers, and A. Laschewsky Spectroscopic properties of mixed Langmuir-Blodgett films of rhodamine dyes and poly(N, N-diallyl-N-octadecylamine-alt-maleic acid) Thin Solid Films 516 2008 2109