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Naphthalene bridged cyclic nitrogen heterocyclic carbene silver complex and its preparation method and application

A nitrogen heterocycle and complex technology, applied in the field of metal organic chemistry, to achieve the effect of obvious fluorescence photosensitive effect

Inactive Publication Date: 2019-10-11
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the coordination mode between N-heterocyclic carbene ligands and metals is similar to that of organic phosphine ligands, the good stability of carbene-metal complexes to water, heat and air is unmatched by phosphine ligand metal complexes

Method used

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  • Naphthalene bridged cyclic nitrogen heterocyclic carbene silver complex and its preparation method and application
  • Naphthalene bridged cyclic nitrogen heterocyclic carbene silver complex and its preparation method and application
  • Naphthalene bridged cyclic nitrogen heterocyclic carbene silver complex and its preparation method and application

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Experimental program
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Embodiment 1

[0034] Preparation of 1,8-bis(2'-chloroacetyl)aminonaphthalene (W)

[0035] In a 250 mL three-neck flask, dissolve 1,8-diaminonaphthalene (10.000 g, 63.2 mmol) in triethylamine (21.0 mL, 151.6 mmol) in CH 2 Cl 2 (120 mL) of the suspension was stirred at 0˚C for 30 min. Chloroacetyl chloride (11.4 mL, 151.7 mmol) was then added dropwise to the above suspension, and stirring was continued at 25 °C for 3 h. The mixture was filtered and washed with water to give 1,8-bis(2'-chloroacetyl)aminonaphthalene (W) as a yellow powder. Yield: 15.731 g (80%). Melting point: 265-267˚C. 1 H NMR (400 MHz, DMSO- d 6 ): δ 4.36 (s, 4H, C H 2), 7.53 (t, J = 3.4 Hz, 6H, Ph H ), 7.90 (t, J = 4.6 Hz, 2H, Ph H ), 10.10 (s, 2H, N H ). 13 C NMR (100 MHz, DMSO- d 6 ) : δ 43.8 ( C h 2 ), 126.0 (Ph C ), 127.8 (Ph C ), 132.1 (Ph C ), 135.9 (Ph C ),165.6 ( C =O).

[0036] Preparation of 1,8-bis[2'-(N-ethyl-imidazolinyl)acetamido]naphthalene chloride (Y)

[0037] A solution of 1,8-...

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Abstract

The invention discloses a naphthalene bridged annular n-heterocyclic carbene silver complex, a preparation method thereof and an application of the complex. 1, 8-diaminonaphthalene reacts with chloroacetyl chloride in an organic solvent, and an obtained product (W) reacts with N-ethylimidazole to obtain a product (Y). The product (Y) reacts with silver oxide to obtain the annular n-heterocyclic carbene silver complex (1). The complex (1) serves as a subject, different types of nitrates serve as objects, the subject and the objects are dissolved in the organic solvent at the temperature of 25 DEG C, subject solution is mixed with different object solution at a certain concentration, fluorescence spectra are measured, and the objects recognizable by the subject are found out. The subject istitrated by different-concentration objects recognizable by the subject, and the fluorescence spectra of the subject are measured. The annular n-heterocyclic carbene silver complex has the advantagesof simplicity in preparation and obvious fluorescence sensing effect, can be used for manufacturing a fluorescent molecular recognition system and can be applied to the field of fluorescent chemistry.

Description

[0001] Statement Regarding Funding Research or Development [0002] This invention is carried out under the support of National Natural Science Foundation of China (fund number: 21572159), Tianjin Normal University Youth Fund (fund number: 52XQ1402) and Tianjin Natural Science Foundation (fund number: 11JCZDJC22000). technical field [0003] The invention belongs to the technical field of organometallic chemistry, and relates to a nitrogen-heterocyclic carbene metal complex with a bisimidazolium salt bridged by naphthalene amide as a precursor, more specifically a ring-shaped nitrogen-heterocyclic carbene silver complex and its preparation method, and the study on the fluorescence recognition performance of cyclic nitrogen-heterocyclic carbene-silver complexes. Background technique [0004] In the past two decades, N-heterocyclic carbene has gradually become one of the research hotspots in organometallic chemistry, and it has been applied in the fields of organic synthesis, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/10C09K11/06G01N21/64
Inventor 柳清湘胡则亮赵志翔
Owner TIANJIN NORMAL UNIVERSITY