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Heteroatom-doped flowerene derivatives and synthesis method thereof

A technology for hydrinoflorene and heteroatom, which is applied in the field of heteroatom-doped florene derivatives and the preparation thereof, can solve the problems of low total yield, difficult synthesis of raw materials, inability to synthesize parent structures, etc., and achieves short synthesis steps, Easy bulk preparation, mild effect

Active Publication Date: 2019-08-06
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this route has disadvantages such as difficult synthesis of raw materials, high temperature (1000° C.), low pressure (0.005 Torr) and low total yield (0.7%). These shortcomings prompt us to find a more effective and practical synthetic route.
In 2014, Li Xuexiang et al. efficiently synthesized thia and selenides whose edges were all substituted by alkoxy groups (Angew. Chem. Int. Ed. 2014, 53, 535), but this method could not synthesize its unsubstituted parent structure

Method used

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  • Heteroatom-doped flowerene derivatives and synthesis method thereof
  • Heteroatom-doped flowerene derivatives and synthesis method thereof
  • Heteroatom-doped flowerene derivatives and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: Taking the synthesis of iodofloralene compound as an example, its structural formula is as follows:

[0035]

[0036] Dissolve 2.18g of 1,5,9-triiodotriphenylene (refer to patent for preparation method: 1,5,9-trisubstituted ketone compound and its synthesis method, application number: 201610962972.8) in 100mL of dichloromethane In the flask, 3.6g of m-chloroperoxybenzoic acid (70%wt%) in dichloromethane (100mL) and 1.9mL of trifluoromethanesulfonic acid were added dropwise at room temperature, reacted for 12h at 20°C, and the reaction was completed Finally, remove the solvent, add diethyl ether, filter with suction, wash with diethyl ether, the obtained brown solid is 2.73g of iodofloralene salt compound, the yield is 72%, melting point: >300°C.

[0037] The characterization of the gained iodine salt compound is as follows: IR (KBr, cm -1 ):3083,1701,1642,1549,1370,1241,1176,1029,809,641; 1 H NMR (500MHz, DMSO-d 6 ):δ8.77(s,6H); 19 F NMR (470MHz, DM...

Embodiment 2

[0038] Embodiment 2: Taking the synthesis of thiaflorene as an example, its structural formula is as follows:

[0039]

[0040] Raw materials used and their synthesis methods:

[0041] 1. Synthesis of thia polycyclic aromatic compounds

[0042] Method A: Add 525mg of the iodine salt compound in Example 1 together with 96mg of sulfur powder and 1.6g of cesium carbonate into a Schlenk tube filled with 10mL of dimethyl sulfoxide, under the protection of an inert gas, at 140°C React for 12 hours. After the reaction is completed, add water, then add dichloromethane for extraction, wash the organic phase with water, wash with saturated brine, dry over anhydrous sodium sulfate, concentrate the solvent, add ethanol, and filter with suction. The obtained brown solid is a thia polycyclic aromatic Compound 87.5mg, its yield 50%, melting point: >300°C.

[0043] Method B: 525mg of the iodine salt compound in Example 1 was added together with 6.7mg of copper chloride and 343mg of potas...

Embodiment 3

[0046] Embodiment 3: Taking the synthesis of thiaflorene as an example, its structural formula is as follows:

[0047]

[0048] Add 315mg of the iodine salt compound in Example 1 together with 142mg of selenium powder and 336mg of potassium tert-butoxide into a Schlenk tube containing 8mL of dimethyl sulfoxide, and react at 70°C for 12h under the protection of an inert gas , after the reaction is complete, add water, then add dichloromethane for extraction, wash the organic phase with water, wash with saturated brine, dry over anhydrous sodium sulfate, concentrate the solvent, add ethanol, and filter with suction, the resulting brown solid is mixed with 1.5g of copper powder and 4mL of 1 , 2,3,4-Tetrahydronaphthalene was added to the Schlenk tube together, and reacted at 200°C for 1 hour. After the reaction was completed and cooled, dichloromethane was added, filtered with suction, the filtrate was desolventized, n-hexane was added, and the obtained brown-yellow solid It is...

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Abstract

The invention provides a heteroatom doped sumanene derivative and a synthetic method thereof. The heteroatom doped sumanene derivative has a structural formula as shown in the specification. The raw materials for the method provided by the invention can be prepared easily in a large amount, and the method is short in synthetic step, mild in operation and good in yield. A method of high-temperature pyrolysis is not needed, and the synthetic method has the advantages of being mild in condition and easy for large-amount preparation. According to the invention, an iodine doped sumanene salt compound (I) and selenium doped sumanene (III) are synthesized for the first time, which has originality. The compound (I) has an important value in preparation of other polycyclic aromatic hydrocarbon compounds. A sulfur doped sumanene compound has a special curved surface structure (Buckybowl), is similar to a part of fullerene, and has an important application value in the fields of new material research, supramolecular recognition and the like.

Description

technical field [0001] The invention relates to a heteroatom-doped flowerene derivative and a preparation method thereof. In particular, a heteroatom-doped sumanene derivative formed by introducing heteroatoms into the molecular skeleton of the bowl-shaped aromatic compound Sumanene and a preparation method thereof. Background technique [0002] Buckybowl is a representative class of polycyclic aromatic hydrocarbons with curved surfaces. Its structure is similar to a segment of fullerene or the capping structure of carbon nanotubes. Its biggest feature is its curved surface. , and its shape is similar to a bowl, hence the name. Bucky bowls have novel physical and chemical properties due to their novel and unique structure, and have potential application value in organic optoelectronic materials, such as they can be used to synthesize fullerenes and carbon nanotubes with uniform size and chirality control and curl Graphene and other multi-carbon materials. In addition, as ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D517/16C07D495/16
CPCC07D495/16C07D517/16
Inventor 谭启涛周丹丹张涛许斌刘秉新
Owner SHANGHAI UNIV
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