Weak light frequency up-conversion ternary supramolecular composite system

A supramolecular and system technology, applied in the directions of luminescent materials, chemical instruments and methods, can solve the problems of low up-conversion efficiency of material systems, and achieve the effect of improving up-conversion quantum yield, increasing the probability of vertical transition, and inhibiting aggregation.

Inactive Publication Date: 2013-09-25
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the upconversion efficiency of the material system obtained by the above method is very low, which still limits its application; therefore, it is necessary to find more material systems that can obtain frequency upconversion under weak light fields.

Method used

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  • Weak light frequency up-conversion ternary supramolecular composite system
  • Weak light frequency up-conversion ternary supramolecular composite system
  • Weak light frequency up-conversion ternary supramolecular composite system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation of β-cyclodextrin / 2-chloro-9,10-di(4-methylphenyl)anthracene (β-cyclodextrin / CDTA)

[0031] (1) 2-Chloro-9,10-bis(4-methylphenyl)-9,10-dihydroxyanthracene (compound 1 ) synthesis: burn a 250ml three-necked round-bottom flask to replace N 2 gas three times at N 2 Under air protection, inject 4-bromotoluene (5.5 mL, 0.041 mol) in anhydrous tetrahydrofuran solution (40 mL), cool the system to -78 °C, slowly add t-BuLi (25 mL, 0.062 mol, 1.6M), colorless A white precipitate gradually appeared in the transparent solution. After reacting at -78°C for 30 minutes, the reaction was continued at room temperature for 30 minutes. The system was then cooled to -78°C, and 2-chloroanthraquinone (4 g, 0.016 mol) was injected into THF (60 mL). , the white turbid liquid turned into a wine red turbid liquid. After the dropwise addition, the system was reacted at -78°C for 30 minutes, and the reaction was naturally warmed to room temperature and stirred for 24 hours...

Embodiment 2

[0036] Example 2 Preparation of β-cyclodextrin / 2-cyano-9,10-di(4-tolyl)anthracene (abbreviation: β-cyclodextrin / DTACN)

[0037] (1) Synthesis of 2-cyano-9,10-di(4-tolyl)anthracene (DTACN): under nitrogen atmosphere, add CDTA (0.72 g, 0.0018 mol) prepared in Example 1, CuCN (0.97 g, 0.0108 mol) and NMP (30 mL), stirred, heated to reflux, reacted for 96 hours, the yellow-green turbid liquid gradually became clear, and then a black solid precipitated out. Cool down to 70°C and add FeCl 3 (5.8 g) in concentrated HCl (10 mL) was stirred for 3 hours, filtered with suction, washed with water and dichloromethane, and spin-dried to obtain a black solid, which was purified by silica gel column chromatography (dichloromethane:petroleum ether=0~1:6) , to obtain 0.46 g of a yellow-green solid, which is the luminescent molecule DTACN, with a yield of 66.7%. 1 H NMR (CDCl 3 , ppm): δ=2.55 (s, 6H, CH 3 ), 7.26-7.46d, 12H, Ar-H), 7.76-7.80 (d, 3H, Ar-H), 8.16 (s, 1H, Ar-H ). MS (m / z): 383;...

Embodiment 3

[0040] Example 3 Preparation of β-cyclodextrin / 2-chloro-9,10-di(β-naphthyl)anthracene (abbreviation: β-cyclodextrin / CDNA)

[0041] (1) 2-Chloro-9,10-di(β-naphthyl)-9,10-dihydroxyanthracene (compound 2 ) Synthetic: method is as described in the step (1) in the embodiment one, only need change 4-bromotoluene into 2-bromonaphthalene, obtain tan solid; Column chromatographic purification (dichloromethane: sherwood oil=1:4 ) to obtain a beige solid compound 2 , the molecular structure formula is:

[0042]

[0043] (2) Synthesis of 2-chloro-9,10-di(β-naphthyl)anthracene (CDNA): The method is as described in step (2) in Example 1, and the compound 1 switch to compound 2 , to obtain 1.08 g light yellow needle-like solid cDNA, yield: 24.83%. 1 H NMR (CDCl 3 , ppm): δ = 7.42-8.11 (m, 21H, Ar-H); MS(m / z): 464; Elemental analysis (%): Caled. C, 87.82%; H, 4.55%; Cl, ​​7.62% ; Found C, 87.86%; H, 4.65%; Cl, ​​7.49%. The molecular structural formula is:

[0044]

[0045] (3) P...

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Abstract

The invention belongs to the up-conversion fluorescence field, and concretely discloses a weak light frequency up-conversion ternary supramolecular composite system. The system comprises beta-cyclodextrin, an illuminant and a photosensitizer; the illuminant is a 2,9,10-substituted anthracene derivative; and the photosensitizer is a metalloporphyrin complex. The above material can obtain frequency up-convension fluorescence emitted through the excitation of short waves by long waves in a weak light field (1W*cm<-2>, and the highest up-conversion efficiency can reach 22.6%. The system has a wide application prospect in the solar photovoltaic field, the solar photocatalysis field, the environmental photochemical technology field and the like.

Description

technical field [0001] The invention belongs to the field of up-conversion fluorescent materials, and specifically relates to a ternary supramolecular system composed of 2,9,10-substituted anthracene derivatives and metal porphyrin complexes enveloped by β-cyclodextrin. Background technique [0002] The emergence of high-energy pulsed lasers has confirmed that substances can undergo two-photon absorption under strong light fields, realize long-wave excitation and short-wave emission, and achieve frequency up-conversion (Up-conversion). Two-photon upconversion has shown high application value in high-tech fields such as three-dimensional optical storage, laser light limiting, upconversion lasing, three-dimensional fluorescence microscopy and photodynamic cancer treatment, which has aroused great interest in the scientific community. [0003] However, two-photon "upconversion" requires intense optical excitation with high peak power, with pulse intensities up to MW×cm -2 ~GW×...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
Inventor 王筱梅孙彬王晶晶叶常青丁平王宝梁作芹
Owner SUZHOU UNIV OF SCI & TECH
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