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Fluorescent nanoparticle solution, as well as preparation method and application thereof
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A technology of fluorescent nanometers and particles, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of no literature reports, etc., and achieve the effect of broad application prospects
Inactive Publication Date: 2012-11-07
NANKAI UNIV
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[0003] Tetraphenylethylene and its derivatives, due to their aggregation-induced emission characteristics, exhibit strong fluorescence in the aggregated state, see (1) J.Liu, J.W.Y.Lam, B.Z.Tang.Chem.Rev.2009,109,5799-5867; (2) M.Wang, G.Zhang, D.Zhang, D.Zhu, B.Z.Tang.J.Mater.Chem.2010,20,1858–1867, received more and more attention, so they are used as fluorescent detectors Needles and organic electroluminescent materials are widely used in the fields of detection, sensing and preparation of organic electroluminescent devices, see (1) Y.Liu, C.Deng, L.Tang, A.Qin, R.Hu, J.Z. Sun, B.Z.Tang.J.Am.Chem.Soc.2011,133,660-663, but these reports are rarely involved in the study of its supramolecular assembly behavior and assembly
In these upper / lower edge modifications, the upper edge sulfonation of calixarene not only brings it good water solubility, but also improves its binding ability to organic guest molecules, see D.-S.Guo, K. Wang, Y.Liu.J.Inclusion Phenom. & Macrocyclic Chem.2008, 62, 1–21, thus greatly opened up the research on the assembly of calixarene, which includes the use of sulfonated calixarene to construct amphiphilic materials, see K.Wang, D.-S.Guo, Y.Liu.Chem.Eur, J.2010, 16, 8006-8011, also used bridged sulfonated calixarene to construct linear supramolecular polymers, see D.-S .Guo, Y.Liu.Chem.Soc.Rev.2012, in press, but so far there are few literature reports on sulfonated calixarene-induced aggregation of organic cations to form nanoparticles and accompanying supramolecules from non-fluorescence to fluorescence emission self-assembly behavior
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Embodiment 1
[0020] A preparation method of the fluorescent nanoparticle solution, comprising the following steps:
[0021] 1) Dissolve 1896 mg (0.003 mol) of 1,2-bis[4-(4-bromobutoxy)phenyl]-1,2-stilbene in 0.05 L of tetrahydrofuran, stir under ice bath, and pour in 0.12 mol of trimethylamine gas, the reaction mixture was warmed to room temperature, and after stirring for 24 hours, 0.01 L of water was added, the mixture was stirred for 24 hours, and the solvent was removed by rotary evaporation. Solid, 51% yield.
[0022] 1 H NMR (400MHz, D 2 O,δ): 6.86-6.69(m,14H), 6.30(br,4H), 3.46(d,4H), 3.12(br,4H), 2.91(d,18H), 1.49(br,8H); ESI -MS: 673.3 (MBr) + ,296.5((M-2Br) / 2) + .
[0023] 2) Dissolve the light yellow TPE solid and SC4A prepared above into water and mix them uniformly to prepare a fluorescent nanoparticle solution. The concentrations of TPE and SC4A used are 0.000072mol / L and 0.000036mol / L, respectively.
[0024] figure 1 a is the fluorescence spectrum after the interacti...
Embodiment 2
[0029]A preparation method of the fluorescent nanoparticle solution, comprising the following steps:
[0030] 1) Dissolve 1896 mg (0.003 mol) of 1,2-bis[4-(4-bromobutoxy)phenyl]-1,2-stilbene in 0.05 L of tetrahydrofuran, stir under ice bath, and pour in 0.12mol of trimethylamine gas, the reaction mixture was warmed to room temperature, and after stirring for 24 hours, 0.01 L of water was added, the mixture was stirred for 24 hours, and the solvent was removed by rotary evaporation. Solid, 51% yield.
[0031] 1 H NMR (400MHz, D 2 O,δ): 6.86-6.69(m,14H), 6.30(br,4H), 3.46(d,4H), 3.12(br,4H), 2.91(d,18H), 1.49(br,8H); ESI -MS:673.3(M-Br) + ,296.5((M-2Br) / 2) + .
[0032] 2) Dissolve the light yellow TPE solid and bisSC4A prepared above into water and mix them uniformly to prepare a fluorescent nanoparticle solution. The concentrations of TPE and bisSC4A used are 0.000072 mol / L and 0.000018 mol / L, respectively.
[0033] figure 1 b is the fluorescence spectrum after the inte...
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Abstract
The invention provides a fluorescent nanoparticle solution. A building unit of the fluorescent nanoparticle uses sulfonato calix[4]arene derivative as the host and tetraphenylethylenequaternaryammonium salt as the guest. A supramolecular assembly is built through interactions of inclusion and complexation of the host-guest among the building units. The sulfonato calix[4]arene derivative is a single-bridged sulfonato calix[4]arene containing a sulfonato calix[4]arene unit or double-bridged sulfonato calix[4]arene containing two sulfonato calix[4]arene units. A preparation method provided by the invention is as follows: tetraphenylethylenequaternaryammonium salt is firstly prepared, and then tetraphenylethylenequaternaryammonium salt and sulfonato calix[4]arene derivative are dissolved into water and mixed uniformly to obtain the final product. The fluorescent nanoparticle solution provided by the invention has the advantages that: (1) the nanoparticle has the specific gathered fluorescence emission characteristic of tetraphenylethylene and the tetraphenylethylene derivatives; and (2) with the fluorescent nanoparticle, a high sensitive sensing to 2,4,6-trinitrophenol can be realized, which means that the fluorescent nanoparticle has a broad application prospects in the sensing technology field of explosive nitro compounds.
Description
【Technical field】 [0001] The invention belongs to the technical field of nano-supramolecular materials, in particular to a fluorescent nano-particle solution and a preparation method and application thereof. 【Background technique】 [0002] In recent years, the construction of functionalized nanoparticles has been one of the research hotspots of chemical and material scientists, see (1) M.Sastry, M.Rao, K.N.Ganesh.Acc.Chem.Res.2002,35,847–855 ;(2) H.Goesmann,C.Feldmann.Angew.Chem.Int.Ed.2010,49,1362–1395, among which fluorescent nanoparticles are unique due to their unique properties in fluorescencemicroscopy, immunolabeling and sensing More attention has been paid to performance, see (1) A.Palma, L.A.Alvarez, D.Scholz, D.O.Frimannsson, M.Grossi, S.J.Quinn, D.l F.O'Shea.J.Am.Chem.Soc.2011, 133 , 19618–19621; (2) X. Zhao, R. Tapec-Dytioco, W. Tan. J. Am. Chem. Soc. 2003, 125, 11474–11475. In the construction of these nanoparticles, most of them are purely inorganic nanopart...
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