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High fluorescence emitted POSS substituted perylene diimide crystal and preparation method

A perylene diimide and fluorescence emission technology, applied in chemical instruments and methods, luminescent materials, silicon organic compounds, etc., can solve the problem of low fluorescence quantum yield of solid perylene imide derivatives and achieve high stability , strong absorption, and enhanced fluorescence quantum yield

Inactive Publication Date: 2012-10-24
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention provides POSS substituted perylene diimide crystals with high fluorescence emission and a preparation method thereof, which are used to solve the technical problem of low fluorescence quantum yield of the above-mentioned solid perylene imide derivatives

Method used

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  • High fluorescence emitted POSS substituted perylene diimide crystal and preparation method
  • High fluorescence emitted POSS substituted perylene diimide crystal and preparation method
  • High fluorescence emitted POSS substituted perylene diimide crystal and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] Preparation of compound crystals of formula (III): use good solvent chloroform to configure unsaturated solution (7.4 mg / ml) of compound of formula (III); configure the crystal growth system in the container from bottom to top as the above-mentioned unsaturated solution, The buffer layer (volume ratio 1:1) of the good solvent chloroform / poor solvent methanol mixture and the poor solvent methanol layer, the unsaturated solution layer, the buffer layer, and the volume ratio of the methanol layer are 3:5:30; with the solvent Interdiffusion between layers, precipitation at the bottom of the container as image 3 Flat ribbon-shaped crystals of the compound of formula (III) shown.

[0053] see figure 1 , the crystal fluorescence emission peak (11) of the compound of formula (III) is 624 nm, and the fluorescence emission peak (12) of the compound of formula (III) is 649 nm in the amorphous solid.

[0054] see figure 2 , the characteristic peaks of the X-ray dif...

Embodiment 2

[0057]

[0058] Preparation of compound crystals of formula (IV): Add 1 mg of amorphous solid of formula (IV) to 5 ml of chloroform solvent, add the resulting solution dropwise into acetone, a poor solvent, and immediately precipitate as Image 6 Needle crystals of the compound of formula (IV);

[0059] see Figure 4 , the fluorescence emission peak (21) of the formula (IV) compound crystal is 646 nm, and the fluorescence emission peak (22) of the formula (IV) compound amorphous solid is 658 nm.

[0060] see Figure 5 , the characteristic peaks of the X-ray diffraction pattern (23) of the compound of formula (IV) show that the compound of formula (IV) is amorphous no matter in a small angle with a 2θ angle of less than 10° or in a wide angle between 10° and 60°. The solid diffraction pattern (24) has many sharp diffraction peaks, showing obvious crystal features.

[0061] The fluorescence quantum yield of the crystal of the compound of formula (IV) is 35.57%, and the flu...

Embodiment 3

[0063]

[0064] Preparation of compound crystals of formula (V): Add THF as a good solvent into a petri dish, cover with a watch glass and place it for 30-60 minutes to form a saturated atmosphere of THF; place the mica sheet in a saturated atmosphere of THF, and then place the ) compound tetrahydrofuran dilute solution (0.5mg / ml) was dropped on the mica sheet, quickly cover the petri dish, and put the whole device in a non-disturbing environment to prevent the crystal growth process from being affected. After the solvent has evaporated, it will form on the mica sheet such as Figure 9 Ribbon crystals of the compound of formula (V) shown.

[0065] Such as Figure 7 , the fluorescence emission peak (31) of the formula (V) compound crystal is 622nm, and the fluorescence emission peak (32) of the formula (V) compound amorphous solid is 648nm.

[0066] Such as Figure 8 , the characteristic peaks of the X-ray diffraction pattern (33) of the compound of formula (V) are higher...

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Abstract

The invention provides a high fluorescence emitted POSS substituted perylene diimide crystal and a preparation method. Due to obstruction of a POSS substituent group structure and a crystal lattice, the crystal obstructs the accumulation of perylene nucleus, the intermolecular PI-PI interaction is non-continuous, the fluorescence quenching can be prevented, and the crystal has high fluorescence emissivity. The preparation method is characterized by taking a corresponding amorphous solid as a raw material and crystallizing to obtain the crystal. The fluorescence quantum yield of the high fluorescence emitted POSS substituted perylene diimide crystal is 2-3 times of that of the amorphous solid, the POSS substituted perylene diimide crystal has strong and wide absorption in a 200-600nm ultraviolet-visible area, and has strong fluorescence emission performance at about 600-680nm. The POSS substituted perylene diimide crystal can be taken as a fluorescence functional organic crystal material which has wide application value in the biomedical fields such as organic light-emitting diodes, opticaly-pumped laser, field effect transistors, chemical sensors, microelectronic fields, biomolecule fluorescent labels, detection, screening and enrichment.

Description

technical field [0001] The invention belongs to the technical field of crystal materials with high fluorescence emission, and in particular relates to a POSS-substituted perylene diimide crystal with high fluorescence emission and a preparation method thereof. Background technique [0002] 3,4,9,10-Perylenetetracarboxylic diimide (PTCDI, referred to as peryleneimide) has excellent chemical stability, heat resistance, light resistance and radiation resistance. The large fused ring structure and large π-electron conjugated system in its molecular structure, as well as its good molecular planarity, make it have extremely strong photoelectric and fluorescent properties, and its fluorescence quantum yield is close to that of a single molecule in a dilute solution. 100%. These excellent properties make it have broad application prospects in the fields of organic light-emitting diodes (OLEDs), laser materials, bioluminescent probe molecules, liquid crystal display materials, molec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/21C09K11/06
Inventor 孙宾朱美芳张文斌刘洋贾朔珣
Owner DONGHUA UNIV
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