Carbazole 1, 3-site Friedel-Crafts ring-closing cyclic compound and preparation method thereof

A technology for cyclic compounds and compound structures, applied in organic chemistry and other directions, can solve the problems of difficult separation and low synthesis yield

Pending Publication Date: 2020-10-27
NANJING UNIV OF POSTS & TELECOMM
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Problems solved by technology

However, it was found that this kind of lattice has potential chirality due to the potential chirality at the 9th position of the fluorenyl group. In the non-stereoselective lattice reaction, a large number of chiral isomers will be formed, resulting in low synthesis yield and difficult separation.

Method used

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  • Carbazole 1, 3-site Friedel-Crafts ring-closing cyclic compound and preparation method thereof
  • Carbazole 1, 3-site Friedel-Crafts ring-closing cyclic compound and preparation method thereof
  • Carbazole 1, 3-site Friedel-Crafts ring-closing cyclic compound and preparation method thereof

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preparation example Construction

[0040] A kind of preparation method of the cyclic compound of carbazole 1,3 Friedel-Crafts ring closure, specifically comprises the following steps:

[0041] The first step: synthesize the Grignard reagent from p-bromobenzene or its derivatives, and then react the prepared Grignard reagent with fluorenone or its derivatives to obtain a type I di-tertiary alcohol synthon;

[0042] The second step: the obtained type I di-tertiary alcohol synthon is reacted with carbazole or its derivatives at room temperature with an acid as a catalyst in a dry organic solvent to obtain the carbazole 1,3 A cyclic compound with a Friedel-Crafts ring.

[0043]

Embodiment 1

[0045] Embodiment 1: the preparation of DBDFOH-I type tertiary alcohol synthon 1

[0046] Dry all the glass instruments to be used in advance (magnets, long needles, two two-necked flasks, and two spherical condenser tubes); steam THF in advance (during the distillation of tetrahydrofuran, a small amount of benzophenone needs to be added to color, when there is no water in the flask, the bottle turns dark blue, at this time tetrahydrofuran can be collected for experiment); then the glass instrument is assembled, magnesium grains (3.06g, 0.127mol) and a grain of iodine (2.54mg, 0.02 mmol) was added (vacuum grease, sealing tape) to one of the instruments, vacuumed three times, and protected by a nitrogen balloon. Dissolve the steamed THF (60 mL) in 1,4-dibromobenzene (10 g, 0.042 mol) that has been evacuated and supplemented with nitrogen, dissolve it, inject it into the reactor with a syringe, and blow hot air to initiate the reaction. Then slowly add the drug (the remaining d...

Embodiment 2

[0047] Embodiment 2: Preparation of LBDFOH-I type tertiary alcohol synthon 2

[0048] Dry all the glass instruments to be used in advance (magnets, long needles, two two-necked flasks, and two spherical condenser tubes); steam THF in advance (during the distillation of tetrahydrofuran, a small amount of benzophenone needs to be added to color, when there is no water in the flask, the bottle turns dark blue, at this time tetrahydrofuran can be collected for experiment); then the glass instrument is assembled, magnesium grains (2.34g, 0.096mol) and a grain of iodine (2.54mg, 0.02 mmol) was added (vacuum grease, sealing tape) to one of the instruments, vacuumed three times, and protected by a nitrogen balloon. Dissolve the evaporated THF (90mL) in 4,4'-dibromobiphenyl (10g, 0.032mol) that has been evacuated and supplemented with nitrogen, dissolve it, inject it into the reactor with a syringe, and blow hot air to initiate the reaction. Then slowly add the drug (the remaining dru...

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Abstract

The invention discloses a carbazole 1, 3-site Friedel-Crafts ring-closing cyclic compound and a preparation method thereof. The compound is a chirality-free I-type di-tert-alcohol synthon composed offluorenyl and phenyl or derivatives of fluorenyl and phenyl, a closed lattice structure which is clear and lasting in shape is formed by connecting the ninth position of fluorenyl with the first siteand the third site of carbazole, the compound has clear side length and vertex on the nanoscale, and due to the obvious length, width and height attributes, the molecular rigidity is higher. The general molecular formula is as shown in the specification. The reaction breaks through the 3, 6-site ring-closing mode of carbazole in the previous Friedel-Crafts reaction, realizes a new method for 1, 3-site ring-closing of carbazole by a simple method, has a deep research value, and has the advantages of no metal catalysis, greenness, environmental protection and atom economy. Meanwhile, the molecule has the advantages of regular structure, adjustable cavity size and easiness in expansion, so that the molecule is worthy of deep research in the fields of organic molecular materials and photoelectric high and new technologies.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a cyclic compound with Friedel-Crafts ring closure at the 1,3-position of carbazole and a preparation method thereof. Background technique [0002] In 2014, Prof. Xie Linghai’s research group proposed a novel structurally rigid nanoscale three-dimensional closed-loop structure—organic nanolattice (L.Wang, G.-W.Zhang, C.-J.Ou, L.-H.Xie , J.-Y. Lin, Y.-Y. Liu and W. Huang, Org. Lett., 2014, 16, 1748-1751). From the analysis of the geometric structure, the grid is a closed-loop structural unit different from the macrocycle, which has obvious edges and corners, vertices and side lengths. Although some structures of macrocyclic compounds with regular corners have also been reported, in fact, regular polygonal macrocycles have not attracted the attention of scientists. However, lattices with three-dimensional configurations are the basis for buildi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/10
CPCC07D487/10C07D403/10
Inventor 张广维向佳茵黄维高闯解令海支欣茹
Owner NANJING UNIV OF POSTS & TELECOMM
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