Furan fused boron aza dihydropyrene and synthesis method thereof
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A technology for furan-fused boron nitrogen and heterodihydropyrene, which is applied in the field of furan-fused borazadihydropyrene and its synthesis, and can solve the problems that the potential application characteristics of luminescent materials have not been widely developed.
Pending Publication Date: 2021-12-28
TIANJIN UNIVERSITY OF TECHNOLOGY
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[0009] In recent years, with the advancement of science and technology, the invention of simple synthesis methods and the discovery that boron and nitrogen doping can effectively adjust the photoelectric physical properties of aromatic systems during the research process, boron and nitrogen doped polycyclic conjugated aromatics have successfully attracted people research interest, its potential applications in electronic devices have been extensively studied, but its potential application properties in light-emitting materials have not been extensively developed
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[0042] Embodiment: the synthesis of compound 1,2,3 and 4a-4e;
[0043] 1) Synthesis of Compound 1: Add 3,6-dibromobenzene-1,2-diamine (265.9mg, 1.0mmol, 1.0equiv), glyoxal (87.06mg, 1.5mmol, 1.5equiv) into a 100ml flask, Triethylamine (151.79mg, 1.5mmol, 1.5equiv) was flushed three times with argon, added an argon balloon, and then added 20mL of ethanol with a syringe, and reacted at room temperature for 16h. After the reaction was complete, dichloromethane was dissolved and washed with saturated aqueous sodium bicarbonate solution. The organic layer was collected and dried with anhydrous sodium sulfate. After filtration, the solvent was spin-dried. The product was purified by silica gel column chromatography, and eluted with ethyl acetate and petroleum ether to obtain compound 1 as a white solid.
[0044] 2) Synthesis of compound 2: add compound 1 (287.94mg, 1.0mmol, 1.0equiv) and sodium borohydride (378.25mg, 10.0mmol, 10.0equiv) in a 100ml flask, flush with argon three tim...
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Abstract
The invention aims to provide a design and synthesis method of a furan fused boron aza dihydropyrene polycyclic aromatic hydrocarbon molecule, and provides more schemes for obtaining more efficient organic photoelectric materials. In order to achieve the purpose, the technical scheme adopted by the invention is as follows: 3, 6-bis (furan-3-yl) benzene-1, 2-diamine is taken as a raw material, the furan fused boron aza dihydropyrene large conjugated polycyclic aromatic hydrocarbon and the derivative thereof at a specific position are generated through nitrogen guidance, and the structural formula of the compound is shown in the specification,wherein the R is independent,can be alkane and can also be a substituted or unsubstituted aryl group or heteroaryl group; R1 and R2 are independent, can be substituted or non-substituted aryl, heteroaryl, alkane, cycloalkane, olefin and alkyne, and can also be hydrogen or single substituted halogen atoms X: F, Cl, Br and I. and Ar aryl is a benzene ring, a thiophene ring, a furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, benzopyridine, a naphthalene ring, an anthracene ring, phenene, tetracene, pyrene, linear or angular pentacene, hexacene, indene or fluorene respectively.
Description
technical field [0001] The present invention relates to furan-fused borazadihydropyrene and its synthesis method and its synthesis method, with commercially available 3,6-dibromobenzene-1,2-diamine as raw material, through Suzuki coupling reaction, Lewis Base-directed electrophilic borocyclization reaction, Suzuki coupling reaction can obtain furan-fused borazadihydropyrene and its derivatives. The synthesis method has the characteristics of simple operation, mild reaction conditions, short reaction path and the like. Background technique [0002] Polycyclic aromatic hydrocarbons (PAHs) have attracted widespread attention due to their unique electronic properties and supramolecular properties, making them attractive candidates for organic semiconductor devices such as organic field-effect transistors (OFETs). s ), organic photovoltaic devices (OPV s ) and Organic Light Emitting Diodes (OLEDs s )) candidates. [0003] Since the outermost shell of the boron atom has three ...
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