Abstract
New fluorescence dyes with an alkoxysilane moiety were synthesised by the condensation of 3-(triethoxysilyl)-1-propanamine (3-aminopropyltriethoxysilane) with 4,10-benzothioxanthene-3,1′-dicarboxylic acid anhydride (BTXA) and N,N-dimethylaminonaphthalene-1,8-dicarboxylic acid anhydride (DMANA), which was accompanied by the formation of an imidic bridge. The compounds N-(3-(triethoxysilyl)propyl)-thioxantheno[2,1,9-dej]isoquinoline-1,3-dione (BTX-S) and 4-(N′, N′-dimethyl)-N-(triethoxysilyl)propyl-1,8-naphthalene dicarboxylic acid imide (DMAN-S) were characterised by steady-state and time-resolved fluorescence spectroscopy in chloroform and ethanol. Both conjugates (BTX-S and DMAN-S) exhibited absorption and emission bands in the same region as the un-substituted BTXA and DMANA. An important Stokes shift was observed for DMAN-S in ethanol. A high fluorescence quantum yield was observed for BTX-S in both solvents and for DMAN-S in chloroform. In addition, the newly developed fluorescent silane dyes were covalently attached to the microscopic particles of layered silicates and on the surface of SiO2 wafers as a proof of concept for fluorescence particle (surface) visualisation. The surface wafer modification was precisely characterised by X-ray photoelectron spectroscopy (XPS). Successful covalent linkage onto the particles of layered silicates was proved by confocal laser scanning microscopy technique.
Similar content being viewed by others
References
Ameloot, R., Roeffaers, M., Baruah, M., De Cremer, G., Sels, B., De Vos, D., & Hofkens, J. (2009). Towards direct monitoring of discrete events in a catalytic cycle at the single molecule level. Photochemical & Photobiological Sciences, 8, 453–456. DOI: 10.1039/b821657f.
Arbeloa, F. L., Martínez, V. M., Prieto, J. B., & Arbeloa, I. L. (2002). Adsorption of rhodamine 3B dye on saponite colloidal particles in aqueous suspensions. Langmuir, 18, 2658–2664. DOI: 10.1021/la0113163.
Birks, J. B. (1970). Fluorescence. In Photophysics of aromatic molecules (pp. 84–139). London, UK: Wiley-Interscience.
Bringley, J. F., Penner, T. L., Wang, R., Harder, J. F., Harrison, W. J., & Buonemani, L. (2008). Silica nanoparticles encapsulating near-infrared emissive cyanine dyes. Journal of Colloid and Interface Science, 320, 132–139. DOI: 10.1016/j.jcis.2007.09.006.
Bujdák, J., & Iyi, N. (2005). Molecular orientation of rhodamine dyes on surfaces of layered silicates. Journal of Physical Chemistry B, 109, 4608–4615. DOI: 10.1021/jp0470039.
Bujdák, J., Chorvát, D., Jr., & Iyi, N. (2010). Resonance energy transfer between rhodamine molecules adsorbed on layered silicate particles. Journal of Physical Chemistry C, 114, 1246–1252. DOI: 10.1021/jp9098107.
Capek, I. (2002). Fate of excited probes in micellar systems. Advances in Colloid and Interface Science, 97, 91–149. DOI: 10.1016/s0001-8686(01)00049-5.
Chmela, Š., Danko, M., & Hrdlovic, P. (1999). Preparation, photochemical stability and photostabilizing efficiency of adducts of 1,8-naphthaleneimide and hindered amine stabilizers in polymer matrices. Polymer Degradation and Stability, 63, 159–164. DOI: 10.1016/s0141-3910(98)00088-3.
Chorvat, D., & Chorvatova, A. (2006). Spectrally resolved time-correlated single photon counting: a novel approach for characterisation of endogenous fluorescence in isolated cardiac myocytes. European Biophysics Journal, 36, 73–83. DOI: 10.1007/s00249-006-0104-4.
Czarnik, A. W. (1994). Chemical communication in water using fluorescent chemosensors. Accounts in Chemical Research, 27, 302–308. DOI: 10.1021/ar00046a003.
Czímerová, A., Bujdák, J., & Gáplovsky, A. (2004). The aggregation of thionine and methylene blue dye in smectite dispersion. Colloids and Surfaces A: Physicochemical Engineering Aspects, 243, 89–96. DOI: 10.1016/j.colsurfa.2004.05.002.
Danko, M., Szabo, E., & Hrdlovic, P. (2011). Synthesis and spectral characteristics of fluorescent dyes based on coumarin fluorophore and hindered amine stabilizer in solution and polymer matrices. Dyes and Pigments, 90, 129–138. DOI: 10.1016/j.dyepig.2010.12.006.
Gao, X., He, J., Deng, L., & Cao, H. (2009). Synthesis and characterisation of functionalized rhodamine B-doped silica nanoparticles. Optical Materials, 31, 1715–1719. DOI: 10.1016/j.optmat.2009.05.004.
Hrdlovič, P., Chmela, Š., Danko, M., Sarakha, M., & Guyot, G. (2008). Spectral properties of probes containing benzothioxanthene chromophore linked with hindered amine in solution and in polymer matrices. Journal of Fluorescence, 18, 393–402. DOI: 10.1007/s10895-007-0279-9.
Kawski, A., Kubicki, A., & Kuliński, B. (1993). Unusual absorption and fluorescence properties of 1,6-diphenyl-1,3,5-hexatriene in poly(vinyl alcohol) film. Journal of Photochemistry and Photobiology A: Chemistry, 71, 161–167. DOI: 10.1016/1010-6030(93)85068-j.
Kollár, J., Hrdlovič, P., Chmela, Š., Sarakha, M., & Guyot, G. (2005). Synthesis and transient absorption spectra of derivatives of 1,8-naphthalic anhydrides and naphthalimides containing 2,2,6,6-tetramethylpiperidine; triplet route of deactivation. Journal of Photochemistry and Photobiology A: Chemistry, 170, 151–159. DOI: 10.1016/j.jphotochem.2004. 07.021.
Kollár, J., Hrdlovič, P., & Chmela, S. (2009). Synthesis and spectral characteristics of substituted 1,8-naphthalimides: Intramolecular quenching by mono-nitroxides. Journal of Photochemistry and Photobiology A: Chemistry, 204, 191–199. DOI: 10.1016/j.jphotochem.2009.03.018.
Konstantinova, T., Lazarova, R., Venkova, A., & Vassileva, V. (2004). On the synthesis and photostability of some new naphthalimide dyes. Polymer Degradation and Stability, 84, 405–409. DOI: 10.1016/j.polymdegradstab.2003.11.016.
Lakowicz, J. R. (2006). Solvent and environmental effects. In Principles of fluorescence spectroscopy (3rd ed., pp. 205–216). New York, NY, USA: Springer Science.
Lenhart, J. L., van Zanten, J. H., Dunkers, J. P., & Parnas, R. S. (2000a). Interfacial response of a fluorescent dye grafted to glass. Langmuir, 16, 8145–8152. DOI: 10.1021/la000553n.
Lenhart, J. L., van Zanten, J. H., Dunkers, J. P., Zimba, C. G., James, C. A., Pollack, S. K., & Parnas, R. S. (2000b). Immobilizing a fluorescent dye offers potential to investigate the glass/resin interface. Journal of Colloid and Interface Science, 221, 75–86. DOI: 10.1006/jcis.1999.6577.
Lenhart, J. L., van Zanten, J. H., Dunkers, J. P., & Parnas, R. S. (2002). Using a localized fluorescent dye to probe the glass/resin interphase. Polymer Composites, 23, 555–563. DOI: 10.1002/pc.10456.
Martin, H. J., Schulz, K. H., Bumgardner, J. D., & Walters, K. B. (2008). An XPS study on the attachment of triethoxsilylbutyraldehyde to two titanium surfaces as a way to bond chitosan. Applied Surface Science, 254, 4599–4605. DOI: 10.1016/j.apsusc.2008.01.066.
Nakashima, K., Winnik, M. A., Dai, K. H., Kramer, E. J., & Washiyama, J. (1992). Fluorescent probe studies on the microstructure of polystyrene-poly(vinylpyridine) diblock copolymer film. Macromolecules, 25, 6866–6870. DOI: 10.1021/ma00051a022.
Nedelčev, T., Račko, D., & Krupa, I. (2008). Preparation and characterisation of a new derivative of rhodamine B with an alkoxysilane moiety. Dyes and Pigments, 76, 550–556. DOI: 10.1016/j.dyepig.2006.11.002.
de Silva, A. P., Gunarante, H. Q. N., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P., Rademacher, J. T., & Rice, T. E. (1997). Signaling recognition events with fluorescent sensors and switches. Chemical Reviews, 97, 1515–1566. DOI: 10.1021/cr960386p.
Trindade, F. J., Fernandes, G. J. T., Araújo, A. S., Fernandes, V. J., Jr., Silva, B. P. G., Nagayasu, R. Y., Politi, M. J., Castro, F. L., & Brochsztain, S. (2008). Covalent attachment of 3,4,9,10-perylenediimides onto the walls of mesoporous molecular sieves MCM-41 and SBA-15. Microporous and Mesoporous Materials, 113, 463–471. DOI: 10.1016/j.micromeso.2007.12.013.
Trindade, F. J., Rey, J. F. Q., & Brochsztain, S. (2011). Covalent attachment of 4-amino-1,8-naphthalimides onto the walls of mesoporous molecular sieves MCM-41 and SBA-15. Dyes and Pigments, 89, 97–104. DOI: 10.1016/j.dyepig.2010.09.009.
Tronc, F., Mei, L., Lu, J., Winnik, M. A., Kaul, B. L., & Graciet, J. C. (2003). Fluorescent polymer particles by emulsion and miniemulsion polymerization. Journal of Polymer Science Part A: Polymer Chemistry, 41, 766–778. DOI: 10.1002/pola.10619.
Wahab, M. A., Sudhakar, S., Elaine, Y., & Sellinger, A. (2008). Evaporation-induced self-assembly of mesoscopically ordered organic/organosilica nanocomposite thin films with photoluminescent properties and improved hardness. Chemistry of Materials, 20, 1855–1861. DOI: 10.1021/cm702753b.
Wahab, M. A., & He, C. (2009). Self-assembly, optical and mechanical properties of surfactant-directed biphenyl-bridged periodic mesostructured organosilica films with molecular-scale periodicity in the pore walls. Langmuir, 25, 832–838. DOI: 10.1021/la803192z.
Wahab, M. A., Hussain, H., & He, C. (2009). Photoactive perylenediimide-bridged silsesquioxane functionalized periodic mesoporous organosilica thin films (PMO-SBA15): Synthesis, self-assembly, and photoluminescent and enhanced mechanical properties. Langmuir, 25, 4743–4750. DOI: 10.1021/la900042g.
Winnik, F. M., & Regismond, S. T. A. (1996). Fluorescence methods in the study of the interactions of surfactants with polymers. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 118, 1–39. DOI: 10.1016/0927-7757(96)03733-8.
Zimerman, O. E., & Weiss, R. G. (1998). Static and dynamic fluorescence from α,ω-di(1-pyrenyl)alkanes in polyethylene films. Control of probe conformations and information about microstructure of the media. Journal of Physical Chemistry A, 102, 5364–5374. DOI: 10.1021/jp972758j.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Professor Štefan Toma on the occasion of his 75th birthday
An erratum to this article is available at http://dx.doi.org/10.2478/s11696-014-0619-6.
Rights and permissions
About this article
Cite this article
Danko, M., Mičušík, M., Omastová, M. et al. Spectral characterisation of new organic fluorescent dyes with an alkoxysilane moiety and their utilisation for the labelling of layered silicates. Chem. Pap. 67, 18–28 (2013). https://doi.org/10.2478/s11696-012-0249-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-012-0249-9