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A technology of benzocoronet dimer and synthesis method, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as insufficient stability of intermediates, low total yield of routes, harsh conditions, etc. , to achieve the effect of regular molecular arrangement, widening range and high stability
Pending Publication Date: 2022-04-15
SHANGHAI NORMAL UNIVERSITY
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However, using this reaction to synthesize the corresponding compound requires more steps (13 steps), the stability of intermediates (thiones and azides) is not good enough, the conditions are harsh and the overall yield of the route is very low
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Embodiment 1
[0049] see figure 1 As shown in the technical process, this embodiment provides a synthetic method of hexabenzocoronene dimer, using the following steps:
[0050] (1) 7,8-bis(dodecyloxy)anthracene-1,4-dione (compound 1) was synthesized according to literature. (References: Org. Lett. 2009, 11(11), 2225-2228.)
[0051] (2) Under nitrogen atmosphere, add 1,2 , 4,5-Tetrakis(bromomethyl)benzene (2.25g, 5mmol, 1.0eq) and potassium iodide (9.96g, 60mmol, 12.0eq). The brown suspension was stirred at 150° C. under nitrogen for 24 hours, then 100 mL of methanol was added at room temperature. The resulting brown solid was filtered and dried. The insoluble solid was used in the next step without further purification.
[0052] Under nitrogen atmosphere, the above solid was dissolved in 100 mL of chlorobenzene, then triphenylphosphine (15.74 g, 60 mmol, 12.0 eq) and carbon tetrachloride (9.64 mL, 100 mmol, 20.0 eq) were added. The solution was refluxed for 24 hours under the protecti...
Embodiment 2
[0064] Compared with Example 1, most of them are the same, except that in this example, 7,8-bis(dodecyloxy)anthracene-1,4-dione, 1,2,4,5-tetra( The molar weights of bromomethyl)benzene, potassium iodide, triphenylphosphine and carbon tetrachloride were adjusted to 2eq, 10eq, 10eq, 18eq respectively.
Embodiment 3
[0066] Compared with Example 1, most of them are the same, except that in this example, 7,8-bis(dodecyloxy)anthracene-1,4-dione, 1,2,4,5-tetra( The molar weights of bromomethyl)benzene, potassium iodide, triphenylphosphine and carbon tetrachloride were adjusted to 2.5eq, 14eq, 14eq, 22eq respectively.
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Abstract
The invention relates to a synthesis method of a hexabenzocoronene dimer. A skeleton is introduced in advance, so that the stability of an intermediate and the reaction yield are greatly improved. The preparation method comprises the following steps: firstly synthesizing a polybenzopolyquinone skeleton through a D-A reaction, then obtaining a dichloroethylene intermediate through a Corey-Fuchs reaction, obtaining a polyaryl intermediate through a Suzuki-Miyaura (Suzuki-Miyaura) reaction, and finally generating the c-HBC dimer through a ring closing reaction. Compared with the prior art, the synthesis method disclosed by the invention is relatively simpler, the obtained product molecules have C2 symmetry axis, the crystallization is good, the molecular arrangement is regular, the potential application of the hexabenzocoronene dimer in the fields of semiconductor transistors, organic photovoltaic cells, chiral optics and the like is facilitated, and the application prospect is wide. And meaningful exploration, material storage and the like are provided for meeting future requirements of semiconductor devices.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a synthesis method of hexabenzocoronene dimer. Background technique [0002] In recent years, organic photoelectric functional materials have been rapidly developed and applied in many emerging fields due to their unique advantages (solution processing, printed electronics, flexibility, low consumption, etc.), such as organic light-emitting diodes (OLEDs), organic photovoltaic cells (OSL) , Organic Field Effect Transistor (OFET), etc. However, in order to further improve the performance of these devices, it is necessary to regulate these molecules structurally. Graphene nanoribbons exhibit unique electrical and optical properties that are strongly dependent on their chemical structure, especially the bandwidth and edge structure. Graphene nanoribbons are obtained by bottom-up solution synthesis method, which can precisely control the edge structure, bandwidth, band gap a...
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