A kind of π-conjugated polycyclic aminoisoquinoline compound and its synthesis method and application

A polycyclic aminoisoquinoline and compound technology, which is applied in the fields of organic chemistry and materials science to achieve the effects of long photoluminescence lifetime, strong fluorescence quantum yield and good application prospects

Active Publication Date: 2022-05-24
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, oxidative [4+2] cyclizations using these electron-deficient internal alkenes are very challenging because the two coupling reagents prefer aza-Michael addition reactions

Method used

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  • A kind of π-conjugated polycyclic aminoisoquinoline compound and its synthesis method and application
  • A kind of π-conjugated polycyclic aminoisoquinoline compound and its synthesis method and application
  • A kind of π-conjugated polycyclic aminoisoquinoline compound and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1 Synthesis of π-conjugated polycyclic aminoisoquinolines

[0047] (1) Synthesis of compound 3 by oxidative amination reaction: weighed aryl amidine 1 (0.25 mmol, 1.0 equiv), maleimide 2 (0.50 mmol, 2.0 equiv), Cu(OAc) 2 (9.0 mg, 20.0 mol%) and 2,2'-bipyridine (11.7 mg, 30.0 mol) were placed in a dry reaction tube, and after vacuum-oxygen replacement (three times) through a double row tube, anhydrous was added. DCE (1.0 mL) was stirred at 120 °C for 12 h under an atmosphere of oxygen (1 atm). The solvent was evaporated in vacuo at room temperature and the remaining residue was purified by silica gel column chromatography (n-hexane / EtOAc as eluent) to afford starting material 3.

[0048] (2) Synthesis of compound 4: Place the weighed raw material 3 (0.15 mmol, 1.0 equiv.), TEMPO (0.03 mmol, 20 mol%) in a dry reaction tube, and carry out vacuum-oxygen replacement through double-row tubes (three times) ), isopropanol (3.0 mL) was added, and the mixture was stirre...

Embodiment 2

[0265] Embodiment 2 explores the influence of solvent selection on the synthesis of intermediate compounds in the process of oxidative amination

[0266] With reference to the preparation process of Example 1, when each reaction condition selects the conditions shown in Table 1, the results of the corresponding synthetic intermediate compound 3-a are shown in Table 1:

[0267] Table 1 Results of the synthesis of intermediate compound 3-a in different oxidative amination reaction solvent systems

[0268]

Embodiment 3

[0269] Example 3 Exploring the influence of catalyst selection on the synthesis of intermediate compounds in the process of oxidative amination

[0270] With reference to the preparation process of Example 1, when each reaction condition selects the conditions shown in Table 2, the results of the corresponding synthetic intermediate compound 3-a are shown in Table 2:

[0271] Table 2 Results of the synthesis of intermediate compound 3-a by different oxidative amination catalyst systems

[0272]

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Abstract

The invention discloses a π-conjugated polycyclic aminoisoquinoline compound, a synthesis method and application thereof, and belongs to the fields of organic chemistry and materials science. The invention provides an economical, efficient and green method for synthesizing the novel π-conjugated polycyclic aminoisoquinoline compounds with good atom and reaction steps, and the synthesized novel π-conjugated polycyclic aminoisoquinoline The structure of quinoline compounds has strong fluorescence quantum yield and long photoluminescence lifetime, and can be used in the fields of small molecule fluorescent markers, new optoelectronic materials, etc., and has good application prospects.

Description

technical field [0001] The invention relates to a π-conjugated polycyclic aminoisoquinoline compound, a synthesis method and application thereof, and belongs to the fields of organic chemistry and materials science. Background technique [0002] Fused N-containing heterocycles have become important building blocks in materials science applications due to their structures possessing various special optoelectronic and electromagnetic properties. In this context, there is a continuing and strong need for the design and efficient synthesis of novel N-containing heterocycles. Among many synthetic approaches, transition metal-catalyzed activation of carbon-hydrogen bonds has recently been reorganized as an increasingly viable tool for the preparation of fused N-containing heterocyclic compounds with extended π-conjugated systems. Despite the great progress, the use of transition metal catalysts, especially noble metal Ru-, Rh-, Pd-, and Ir-complexes, makes this strategy still hav...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06
CPCC07D471/04C09K11/06C09K2211/1044C09K2211/1007
Inventor 刘蕾李杰王大伟张钊
Owner JIANGNAN UNIV
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