Unusual Spectral Change Due to a Cyanine Dye Adsorbed on an Inorganic Layered Material upon Photoirradiation

Mari Ishihara^*, Ryuji Hirase, Hideki Yoshioka

Hyogo Prefectural Institute of Technology, Kobe, Japan.

DOI: 10.4236/wjnse.2014.44016                

Abstract

Photoinduced spectral change can be utilized for various optical devices. The photoinduced spectral change due to an organic dye was demonstrated for the organic-inorganic hybrid film without the aid of photochromism with a simple preparation method for the first time. By the hybridization of a cyanine dye of 2-[5-(1,3-dihydro-3,3-dimethyl-1-octadecyl-2H-indol-2-ylidene)-1,3-pentadienyl]-3,3-dimethyl-1-octadecyl-3H-indolium perchlorate (NK3175) with an inorganic layered material of cation-exchangeable clay, smectite (SWN), a spectral change attributed to NK3175 was generated upon the irradiation of UV light. This result might serve as useful information on the methodology to produce optically controlled function for photoresponsive systems. Furthermore, the hybrid film of SWN and NK3175 was characterized by the use of XRD and FT-IR measurements. NK3175 molecules adsorbed onto external surfaces of SWN were confined by oriented SWN. It was suggested that the enhanced intermolecular interaction between NK3175 molecules caused by the hybridization with SWN resulted in the change of the aggregation state of NK3175 upon the UV light irradiation, which accounts for the spectral change of NK3175.

Keywords

Photoinduced Spectral Change, Cyanine Dye, Clay, Hybrid Material

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Ogawa, M. and Kuroda, K. (1995) Photofunctions of Intercalation Compounds. Chemical Reviews, 95, 399-438. http://dx.doi.org/10.1021/cr00034a005
[2]	Shichi, T. and Takagi, K. (2000) Clay Minerals as Photochemical Reaction Fields. Journal of Photochemistry and Photobiology C: Photochemistry Reviews, 1, 113-130. http://dx.doi.org/10.1016/S1389-5567(00)00008-3
[3]	Takagi, S., Shimada, T., Ishida, Y., Fujimura, T., Masui, D., Tachibana, H., Eguchi, M. and Inoue, H. (2013) Size- Matching Effect on Inorganic Nanosheets: Control of Distance, Alignment and Orientation of Molecular Adsorption as a Bottom-Up Methodology for Nanomaterials. Langmuir, 29, 2108-2119. http://dx.doi.org/10.1021/la3034808
[4]	Zhou, C.H., Shen, Z.F., Liu, L.H. and Liu, S.M. (2011) Preparation and Functionality of Clay-Containing Films. Journal of Material Chemistry, 21, 15132-15153. http://dx.doi.org/10.1039/c1jm11479d
[5]	Ras, R.H.A., Umemura, Y., Johnston, C.T., Yamagishi, A. and Schoonheydt, R.A. (2007) Ultrathin Hybrid Films of Clay Minerals. Physical Chemistry Chemical Physics, 9, 918-932. http://dx.doi.org/10.1039/b610698f
[6]	Ogawa, M., Ishii, I., Miyamoto, N. and Kuroda, K. (2003) Intercalation of a Cationic Azobenzene into Montmorillonite. Applied Clay Science, 22, 179-185. http://dx.doi.org/10.1016/S0169-1317(02)00157-6
[7]	Tsukamoto, T., Shimada, T. and Takagi, S. (2013) Unique Photochemical Properties of p-Substituted Cationic Triphenylbenzene Derivatives on a Clay Layer Surface. The Journal of Physical Chemistry C, 117, 2774-2779. http://dx.doi.org/10.1021/jp3092144
[8]	Bujdak, J. (2006) Effect of the Layer Charge of Clay Minerals on Optical Properties of Organic Dyes. Applied Clay Science, 34, 58-73. http://dx.doi.org/10.1016/j.clay.2006.02.011
[9]	Estevez, M.J.T, Arbeloa, F.L. and Arbeloa, T.L. (1994) On the Monomeric and Dimeric States of Rhodamine 6G Adsorbed on Laponite B Surfaces. Journal of Colloid and Interface Science, 162, 412-417. http://dx.doi.org/10.1006/jcis.1994.1055
[10]	Yariv, S., Nasser, A. and Baron, P. (1990) Metachromasy in Clay Minerals. Spectroscopic Study of the Adsorption of Crystal Violet by Laponite. Journal of the Chemical Society, Faraday Transactions, 86, 1593-1598. http://dx.doi.org/10.1039/ft9908601593
[11]	Lucia, L.A., Yui, T., Sasai, R., Yoshida, H., Takagi, S., Takagi, K., Whitten, D.G. and Inoue, H. (2003) Enhanced Aggregation Behavior Antimony (V) Porphyrins in Polyfluorinated Surfactant/Clay Hybrid Microenvironment. The Journal of Physical Chemistry B, 107, 3789-3797. http://dx.doi.org/10.1021/jp026648a
[12]	Takagi, K., Kurematsu, T. and Sawaki, Y. (1991) Intercalation and Photochromism of Spiropyrans on Clay Interlayeres. Journal of the Chemical Society, Perkin Transactions, 2, 1517-1522. http://dx.doi.org/10.1039/p29910001517
[13]	Sasai, R., Ogiso, H., Shindachi, I., Shichi, T. and Takagi, K. (2000) Photochromism in Oriented Thin Films Prepared by the Hybridization of Diarylethenes in Clay Interlayers. Tetrahedron, 56, 6979-6984. http://dx.doi.org/10.1016/S0040-4020(00)00519-6
[14]	Iyi, N., Kurashima, K. and Fujita, T. (2002) Orientation of an Organic Anion and Second-Staging Structure in Layered Double-Hydroxide Intercalates. Chemistry of Materials, 14, 583-589. http://dx.doi.org/10.1021/cm0105211
[15]	Bujdak, J., Iyi, N. and Sasai, R. (2004) Spectral Properties, Formation of Dye Molecular Aggregates and Reactions in Rhodamine 6G/Layered Silicates Dispersions. The Journal of Physical Chemistry B, 108, 4470-4477. http://dx.doi.org/10.1021/jp037607x
[16]	Mishra, A., Behera, R.K., Behera, P.K., Mishra, B.K. and Behera, G.B. (2000) Cyanines during the 1990s: A Review. Chemical Reviews, 100, 1973-2012. http://dx.doi.org/10.1021/cr990402t
[17]	Ogawa, M., Kawai, R. and Kuroda, K. (1996) Adsorption and Aggregation of a Cationic Cyanine Dye on Smectites. The Journal of Physical Chemistry, 100, 16218-16221. http://dx.doi.org/10.1021/jp960261o
[18]	Bujdak, J., Martinez, V.M., Arbeloa, F.L. and Iyi, N. (2007) Spectral Properties of Rhodamine 3B Adsorbed on the Surface of Montmorillonites with Variable Layer Charge. Langmuir, 23, 1851-1859. http://dx.doi.org/10.1021/la062437b
[19]	Sasai, R., Iyi, N., Fujita, T., Arbeloa, F.L., Martinez, V., Takagi, K. and Itoh, H. (2004) Luminescence Properties of Rhodamine 6G Intercalated in Surfactant/Clay Hybrid Thin Solid Films. Langmuir, 20, 4715-4719. http://dx.doi.org/10.1021/la049584z
[20]	Suzuki, Y., Tenma, Y., Nishioka, Y., Kamada, K., Ohta, K. and Kawamata, J. (2011) Efficient Two-Photon Absorption Materials Consisting of Cationic Dyes and Clay Minerals. The Journal of Physical Chemistry C, 115, 20653-20661. http://dx.doi.org/10.1021/jp203809b
[21]	Nakato, T., Kusunoki, K., Yoshizawa, K., Kuroda, K. and Kaneko, M. (1995) Photoluminescence of Tris(2,2’-bipyri- dine)ruthenium(II) Ions Intercalated in Layered Niobates and Titanates: Effect of Interlayer Structure on Host-Guest and Guest-Guest Interactions. The Journal of Physical Chemistry, 99, 17896-17905. http://dx.doi.org/10.1021/j100051a015
[22]	Ichimura, K. (2000) Photoalignment of Liquid-Crystal Systems. Chemical Reviews, 100, 1847-1874. http://dx.doi.org/10.1021/cr980079e
[23]	Ruslim, C., Hashimoto, M., Matsunaga, D., Tamaki, T. and Ichimura, K. (2004) Optical and Surface Morphological Properties of Polarizing Films Fabricated from a Chromonic Dye by the Photoalignment Technique. Langmuir, 20, 95-100. http://dx.doi.org/10.1021/la035366e
[24]	Seki, T. (2007) Smart Photoresponsive Polymer Systems Organized in Two Dimensions. Bulletin of the Chemical Society of Japan, 80, 2084-2109. http://dx.doi.org/10.1246/bcsj.80.2084
[25]	O’Neill, M. and Kelly, S.M. (2011) Ordered Materials for Organic Electronics and Photonics. Advanced Materials, 23, 566-584. http://dx.doi.org/10.1002/adma.201002884
[26]	Kawatsuki, N. (2011) Photoalignment and Photoinduced Molecular Reorientation of Photosensitive Materials. Chemistry Letters, 40, 548-554. http://dx.doi.org/10.1246/cl.2011.548
[27]	Kurihara, S., Nomitama, S. and Nonaka, T. (2001) Photochemical Control of the Macrostructure of Cholesteric Liquid Crystals by Means of Photoisomerization of Chiral Azobenzene Molecules. Chemistry of Materials, 13, 1992-1997. http://dx.doi.org/10.1021/cm0007555
[28]	Moriyama, M., Mizoshita, N., Yokota, T., Kashimoto, K. and Kato, T. (2003) Photoresponsive Anisotropic Soft Solids: Liquid-Crystalline Physical Gels Based on a Chiral Photochromic Gelator. Advanced Materials, 15, 1335-1338. http://dx.doi.org/10.1002/adma.200305056
[29]	Matsumoto, M., Tachibana, H., Sato, F. and Terrettaz, S. (1997) Photoinduced Self-Organization in Langmuir-Blodgett Films. The Journal of Physical Chemistry B, 101, 702-704. http://dx.doi.org/10.1021/jp9629093
[30]	Ishihara, M., Hirase, R., Mori, M., Yoshioka, H. and Ueda, Y. (2009) Photoinduced Spectral Changes in Hybrid Thin Films of Functional Dyes and Inorganic Layered Material. Thin Solid Films, 518, 857-860. http://dx.doi.org/10.1016/j.tsf.2009.07.103
[31]	Irie, M. (2000) Diarylethenes for Memories and Switches. Chemical Reviews, 100, 1685-1716. http://dx.doi.org/10.1021/cr980069d
[32]	Bujdak, J. and Iyi, N. (2006) Molecular Aggregation of Rhodamine Dyes in Dispersions of Layered Silicates: Influence of Dye Molecular Structure and Silicate Properties. The Journal of Physical Chemistry B, 110, 2180-2186. http://dx.doi.org/10.1021/jp0553378
[33]	Iyi, N., Sasai, R., Fujita, T., Deguchi, T., Sota, T., Arbeloa, F.L. and Kitamura, K. (2002) Orientation and Aggregation of Cationic Laser Dyes in a Fluoromica: Polarized Spectrometry Studies. Applied Clay Science, 22, 125-136. http://dx.doi.org/10.1016/S0169-1317(02)00144-8
[34]	Bujdak, J., Iyi, N. and Fujita, T. (2002) The Aggregation of Methylene Blue in Montmorillonite Dispersions. Clay Minerals, 37, 121-133. http://dx.doi.org/10.1180/0009855023710022
[35]	Neumann, M.G., Schmidt, C.C. and Gessner, F. (1996) Time-Dependent Spectrophotometric Study of the Interaction of Basic Dyes with Clays II: Thionine on Natural and Synthetic Montmorillonites and Hectorites. Journal of Colloid and Interface Science, 177, 495-501. http://dx.doi.org/10.1006/jcis.1996.0063
[36]	Fujimoto, Y., Katayama, N., Ozaki, Y., Yasui, S. and Iriyama, K. (1992) Spectroscopic Studies of Thiatri-, Penta-and Heptamethine Cyanine Dyes II. Infrared and Resonance Raman Spectra of Thiatri-, Penta-and Heptamethine Cyanine Dyes. Journal of Molecular Structure, 274, 183-195. http://dx.doi.org/10.1016/0022-2860(92)80157-D
[37]	Sato, H., Kawasaki, M., Kasatani, K. and Katsumata, M. (1988) Raman Spectra of Some Indo-, Thia- and Selena-Carbocyanine Dyes. Journal of Raman Spectroscopy, 19, 129-132. http://dx.doi.org/10.1002/jrs.1250190210
[38]	Yang, J.P. and Callender, R.H. (1985) The Resonance Raman Spectra of Some Cyanine Dyes. Journal of Raman Spectroscopy, 16, 319-321. http://dx.doi.org/10.1002/jrs.1250160507
[39]	Ras, R.H.A., Johnston, C.T., Franses, E.I., Ramaekers, R., Maes, G., Foubert, P., De Schryver, F.C. and Schoonheydt, R.A. (2003) Polarized Infrared Study of Hybrid Langmuir-Blodgett Monolayer Containing Clay Mineral Nanoparticles. Langmuir, 19, 4295-4302. http://dx.doi.org/10.1021/la026786r
[40]	Cao, J.F., Wu, T., Hu, C., Liu, T., Sun, W., Fan, J.L. and Peng, X.J. (2012) The Nature of the Different Environmental Sensitivity of Symmetrical and Unsymmetrical Cyanine Dyes: An Experimental and Theoretical Study. Physical Chemistry Chemical Physics, 14, 13702-13708. http://dx.doi.org/10.1039/c2cp42122d