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Rare earth complex with aggregation-induced fluorescence enhancement effect, probe and preparation method

A technology of rare earth complexes and enhancement effects, applied in the field of probes and their preparation, and functional rare earth complexes, can solve the problems of emission energy level change and difficult emission energy level matching, etc., and achieve enhanced emission intensity, novel physical properties, Effects with simple synthesis steps

Inactive Publication Date: 2015-08-26
SICHUAN NEW MATERIAL RES CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report on the functional metal complexes with aggregation-induced fluorescence enhancement effect, which may be due to the fact that transition metal building blocks and multi-branched non-coplanar organic functional groups are both outer-shell electron transition-induced fluorescence, and the emission energy level is easily affected by the external environment. It is difficult to match the emission levels of the two

Method used

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  • Rare earth complex with aggregation-induced fluorescence enhancement effect, probe and preparation method
  • Rare earth complex with aggregation-induced fluorescence enhancement effect, probe and preparation method
  • Rare earth complex with aggregation-induced fluorescence enhancement effect, probe and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] The principle of the reaction formula is as above.

[0037] Take 4-(1,2,2-triphenylenyl)phenylboronic acid ((4-(1,2,2-triphenylvinyl)phenyl)boronic acid, TPV-B(OH) 2 ) (i.e. 1a), a total of 0.564g, i.e. 1.5mmol, take 4'-chloro-2,2':6',2"-terpyridine (4'-chloro-2,2':6',2"- terpyridine, TPy) (i.e. 1b), a total of 0.267g, i.e. 1mmol, another Pd (PPh 3 ) 4 (0.202g, namely 0.2mmol), K 2 CO 3(2.8g, namely 20mmol) was mixed and dissolved in 120mL of deoxygenated toluene / ethanol / water (volume ratio 8:2:2) mixed solvent, and heated to reflux for 24 hours under the protection of argon. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated. After the organic phase was dried over magnesium sulfate, the solvent was evaporated under reduced pressure, and the obtained crude product was separated by column chromatography to obtain a white solid 4'-(4-(1,2 ,2-triphenylenyl)phenyl)-2,2':6',2"-terpyridine (4'-(4-(1,2,2...

Embodiment 2

[0042]

[0043] The synthesis method of the compound is the same as in Example 1. TPV-B(OH) 2 (1a) with 4'-(4-bromophenyl)-2,2':6',2"-terpyridine (4'-(4-bromophenyl)-2,2':6',2"-terpyridine ) (2b) coupled to give a white solid 4'-(4'-(1,2,2-triphenylvinyl)-[1,1'-biphenyl]-4-yl)-2,2':6',2″ -terpyridine (2c); 2c and rare earth compound Ln (hfac) 3 (H 2 O) 2 Coordination affords the target compound 2d.

Embodiment 3

[0045]

[0046] 2-(4-ethynylphenyl)-1,1,2-triphenylethylene ((2-(4-ethynylphenyl)ethene-1,1,2-triyl)tribenzene) (3a) (0.356g, 1mmol ) with 4'-(4-azidophenyl)-2,2':6',2"-terpyridine (4'-(4-azidophenyl)-2,2':6',2"-terpyridine) (3b) (0.350g, 1mmol) was mixed and dissolved in 8mL tert-butanol / water (1:1, V / V), and sodium ascorbate (0.04g, 0.2mmol) and copper sulfate pentahydrate (0.025 g, 0.1 mmol), stirred at room temperature for about 2 hours, added 30 mL of ethyl acetate, washed with saturated brine (15 mL), separated the organic phase, dried the organic phase with anhydrous sodium sulfate, evaporated the solvent under reduced pressure, and passed the crude product through the column Chromatographic separation gave light yellow oily liquid 4'-(4-(4-(4-(1,2,2-triphenylvinyl)phenyl)-1H-1,2,3-triazol-1-yl)phenyl)-2 ,2':6',2″-terpyridine (3c).

[0047] The compound 3c (1mmol) with AIE effect and the rare earth compound Ln(hfac) 3 (H 2 O) 2 (1 mmol) was mixed and dissolved i...

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Abstract

The invention discloses a rare earth complex with an aggregation-induced luminescence enhancement effect, which comprises multi-branch non-coplanar organic functional groups. Aggregation-induced enhanced energy is transferred to rare earth ions through an 'antenna effect' by using organic functional groups with the aggregation-induced luminescence enhancement effect, so as to obtain the functional rare earth luminescent complex with the aggregation-induced luminescence enhancement effect. According to the invention, the multi-branch non-coplanar organic functional groups are used as bridging ligands, and aggregation-induced emission enhanced emitted energy is transferred to rare earth building blocks through the 'antenna effect' to realize the aggregation-induced luminescence enhancement effect of the functional rare earth complex. The synthesizing step is simple and the accessibility is strong. The system provided by the invention expands the aggregation-induced luminescence enhancement effect from special organic functional groups to a functional rare earth complex system. The complex is expected to have a good application background in chemical sensors, biological probes and solid illuminators.

Description

technical field [0001] The invention relates to a rare earth complex and a preparation method thereof, more specifically to a functional rare earth complex having an aggregation-induced luminescent enhancement effect, a probe and a preparation method thereof. Background technique [0002] The cluster quenching effect affects the sensitivity and performance of high-performance optoelectronic materials in chemical sensors, biological probes, smart nanomaterials, and solid-state light-emitting devices. For example, aromatic hydrocarbons and their derivatives, whose shape is similar to that of a disc, will have a strong π-π stacking effect, causing the fluorescence quenching (ACQ) effect, which greatly limits its detection sensitivity. In biological detection systems, small fluorophore molecules may accumulate on the surface of biomacromolecules and in the hydrophobic cavities of folded structures, which greatly increases the local fluorophore concentration, resulting in a conce...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/00C09K11/06
Inventor 徐海兵张衍焦鹏冲邓建国黄辉
Owner SICHUAN NEW MATERIAL RES CENT
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