Abstract
We prepared imidazolium-containing silica hybrid films by sol–gel reactions of 1-(trimethoxysilylpropyl)-3-methylimidazolium chloride under microwave irradiation. Furthermore, we incorporated hydrophobic dyes such as pyrene and 1-pyrenecarboxaldehyde into the silica hybrids, and we investigated the dispersion behaviors of these dyes in the matrices. The local heating of the imidazolium groups under microwave irradiation was suggested to contribute to the enhancement of reaction rates in the sol–gel process. Finally, we achieved the incorporation of higher dye concentrations in the silica hybrids compared with those achieved with conventional heating.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Dantas de Morais, T., Chaput, F., Lahlil, K. & Boilot, J.-P. Hybrid organic-inorganic light-emitting diodes. Adv. Mater. 11, 107–112 (1999).
Dantas de Morais, T., Chaput, F., Boilot, J.-P., Lahlil, K., Darracq, B. & Lévy, Y. Hole mobilities in sol–gel materials. Adv. Mater. Opt. Electron. 10, 69–79 (2000).
Biteau, J., Chaput, F., Yokoyama, Y. & Boilot, J.-P. Photochromism of an indolylfulgide trapped in a hybrid sol-gel matrix. Chem. Lett. 27, 359–360 (1998).
Rottman, C., Grader, G., De Hazan, Y., Melchior, S. & Avnir, D. Surfactant-induced modification of dopants reactivity in sol−gel matrixes. J. Am. Chem. Soc. 121, 8533–8543 (1999).
Tanaka, K., Jeon, J.-H., Inafuku, K. & Chujo, Y. Enhancements of optical properties of dyes for bioprobes by freezing effect of molecular motion using POSS-core dendrimers. Bioorg. Med. Chem. 20, 915–919 (2012).
Tanaka, K., Murakami, M., Jeon, J.-H. & Chujo, Y. Enhancement of affinity in molecular recognition via hydrogen bonds by POSS-core dendrimer and its application for selective complex formation between guanosine triphosphate and 1,8-naphthyridine derivatives. Org. Biomol. Chem. 10, 90–95 (2012).
Tanaka, K., Ohashi, W., Kitamura, N. & Chujo, Y. Reductive glutathione-responsive molecular release using water-soluble POSS network polymers. Bull. Chem. Soc. Jpn 84, 612–616 (2011).
Tanaka, K., Kitamura, N. & Chujo, Y. Bi-modal quantitative monitoring for enzymatic activity with simultaneous signal increases in 19F NMR and fluorescence using silica nanoparticle-based molecular probes. Bioconjugate Chem. 22, 1484–1490 (2011).
Tanaka, K., Inafuku, K., Naka, K. & Chujo, Y. Enhancement of entrapping ability of dendrimers by a cubic silsesquioxane core. Org. Biomol. Chem. 6, 3899–3901 (2008).
García, O., Garrido, L., Sastre, R., Costela, A. & García-Moreno, I. Synthetic strategies on hybrid materials improving properties for optoelectronic applications. Adv. Funct. Mater. 18, 2017–2025 (2008).
Gilliland, J. W., Yokoyama, K. & Yip, W. T. Solvent effect on mobility and photostability of organic dyes embedded inside silica sol-gel thin films. Chem. Mater. 17, 6702–6712 (2005).
Lei, Q. & Yip, W. T. Probing the effect of post-synthesis grafting on guest-host interactions in sol-gel silica with single-molecule mobility and photostability. J. Phys. Chem. C 113, 21130–21138 (2009).
Ye, F., Collinson, M. M. & Higgins, D. A. What can be learned from single molecule spectroscopy? Applications to sol–gel-derived silica materials. Phys. Chem. Chem. Phys. 11, 66–82 (2009).
Hellriegel, C., Kirstein, J., Brauchle, C., Latour, V., Pigot, T., Lacombe, S., Brown, R., Guieu, V., Payrastre, C., Izquierdo, A. & Mocho, P. Diffusion of single streptocyanine Molecules in the nanoporous network of sol−gel glasses. J. Phys. Chem. B 108, 14699–14709 (2004).
Martínez-Palou, R. Microwave-assisted synthesis using ionic liquids. Mol. Divers 14, 3–25 (2010).
Valkenberg, M. H., deCastro, C. & Hölderich, W. F. Immobilisation of chloroaluminate ionic liquids on silica materials. Top. Catal 14, 139–144 (2001).
Nakajima, A. Variations in the vibrational structures of fluorescence spectra of naphthalene and pyrene in water and in aqueous surfactant solutions. Bull. Chem. Soc. Jpn 50, 2473–2474 (1977).
Kalyanasundaram, K. & Thomas, J. K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 99, 2039–2044 (1977).
Dong, D. C. & Winnik, M. A. The Py scale of solvent polarities. Can. J. Chem. 62, 2560–2565 (1984).
Fretcher, K. A., Storey, I. A., Hendricks, A. E., Pandey, S. & Pandey, S. Behavior of the solvatochromic probes Reichardt’s dye, pyrene, dansylamide, Nile Red and 1-pyrenecarbaldehyde within the room-temperature ionic liquid bmimPF6 . Green Chem. 3, 210–215 (2001).
Acknowledgements
This work was partially supported by the Kansai Research Foundation for the promotion of technology.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kajiwara, Y., Tanaka, K. & Chujo, Y. Enhancement of dye dispersibility in silica hybrids through local heating induced by the Imidazolium group under microwave irradiation. Polym J 46, 195–199 (2014). https://doi.org/10.1038/pj.2013.81
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/pj.2013.81
Keywords
This article is cited by
-
PM-bound polycyclic aromatic compounds (PACs) in two large-scale petrochemical bases in South China: Spatial variations, sources, and risk assessment
Environmental Science and Pollution Research (2023)
-
Recent progress in the development of advanced element-block materials
Polymer Journal (2018)
-
On-demand easy peeling of acrylic adhesives containing ionic liquids through a microwave irradiation stimulus
Polymer Journal (2018)
-
Remarkably high miscibility of octa-substituted POSS with commodity conjugated polymers and molecular fillers for the improvement of homogeneities of polymer matrices
Polymer Journal (2016)
-
Preparation of photo-responsive hybrid materials based on hydrogels involving imidazolium-presenting gold nanoparticles
Polymer Journal (2016)
