A kind of hbc compound containing crown ether and its preparation and application

A compound and crown ether-containing technology, which are applied to supramolecular assembly materials and their preparation and application fields, can solve problems such as reduced efficiency and difficulty, and achieve the effects of simple synthesis method, good solubility and mature preparation technology of raw materials.

Active Publication Date: 2021-07-02
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this strategy of introducing chiral centers through covalent bonds requires a large number of asymmetric synthesis and precise control of their chirality during the assembly process, which is very difficult and greatly reduces the efficiency. We hope Achieving this through non-covalent bonds

Method used

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  • A kind of hbc compound containing crown ether and its preparation and application
  • A kind of hbc compound containing crown ether and its preparation and application
  • A kind of hbc compound containing crown ether and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of Compound 4

[0040] Add 3 (400mg, 1.03mmol), bispinacol diboron (313mg, 1.23mmol), PdCl 2 (dppf) (75mg, 0.103mmol, 10%), KOAc (221mg, 2.25mmol, 3eq.), pumped and exchanged air three times under the protection of Ar gas, added anhydrous DMF (freezing deoxygenation) (20mL), heated to 80°C , reacted for 3 hours, and stopped the reaction. After cooling to room temperature, CH 2 Cl 2 Extract (50mL×3), combine the organic phases, wash with distilled water (50mL×3), dry the organic phase with anhydrous magnesium sulfate, filter to remove the magnesium sulfate, rotary evaporate to remove the solvent, and the residue is purified by silica gel chromatography (eluent : dichloromethane: methanol = 20: 1), to obtain light yellow oil: 200.41mg, yield 61%. 1 H NMR (600MHz, CDCl 3 )δ (ppm) 7.08 (d, J = 7.1Hz, 2H), 6.93 (d, J = 8.4Hz, 1H), 4.23 (d, J = 20.9Hz, 4H), 3.98 (s, 4H), 3.81 ( s,4H),3.75(s,4H),3.72(s,4H),1.27(s,12H). 13 C NMR (150MHz, CDCl 3 ): δ (ppm) 148....

Embodiment 2

[0042] Synthesis of compound 6

[0043] Add compound 5 (5g, 15.36mmol), cuprous iodide (0.293g, 1.54mmol), PdCl 2 (PPh 3 ) 2 (0.66g, 0.9mmol), under the protection of Ar, gas exchanged three times, added DBU (14.24mL), benzene (20mL), trimethylethynyl silicon (TMSA, 1.1mL) and H 2 O (60 μL), heated to 80°C, stopped the reaction after 24 hours and cooled to room temperature. CH 2 Cl 2 Take three times (30mL×3), combine the organic phase, wash the organic phase with 10% HCl, then wash with saturated NaCl, rotary evaporate most of the solvent, add an appropriate amount of silica gel for dry column chromatography, (eluent: petroleum ether) to obtain 2.1 g of a colorless transparent liquid with a yield of 65%. 1 H NMR (600MHz, CDCl 3 ): δ (ppm) 7.45 (d, J = 7.3Hz, 4H), 7.17 (d, J = 7.2Hz, 4H), 2.62 (d, J = 6.6Hz, 4H), 1.62 (s, 4H), 1.30 (d, J = 17.1 Hz, 36H), 0.90 (d, J = 6.5 Hz, 6H). 13 C NMR (150MHz, CDCl 3 ): δ (ppm) 143.6, 131.8, 128.8, 121.0, 89.3, 36.3, 36.2, 31.6, 30...

Embodiment 3

[0045] Synthesis of compound 7

[0046] Add 6 (2.46g, 4.79mmol) to the 500mL two-necked flask, RuO 2 (14mg), add CH3CN / CCl4 / H2O=14mL / 14mL / 21mL in proportion, stir at 25°C for 2.5 hours, distill off the solvent, and use CH 2 Cl 2 Extract (50mL×3), combine the organic phase, dry the organic phase with anhydrous magnesium sulfate, filter to remove the magnesium sulfate, rotary evaporate to remove the solvent, and the residue is purified by silica gel chromatography, (eluent: petroleum ether: dichloromethane =3:1), 1.6 g of a light yellow solid was obtained, and the yield was 85%. 1 H NMR (600MHz, CDCl 3 ): δ (ppm) 7.91 (d, J = 7.9Hz, 4H), 7.33 (d, J = 8.0Hz, 4H), 2.70 (t, J = 7.7Hz, 4H), 1.65 (m, 4H), 1.30 (d, J=18.0Hz, 36H), 0.90 (t, J=6.6Hz, 6H). 13 C NMR (150MHz, CDCl 3 ): δ (ppm) 194.8, 151.2, 131.2, 128.8, 129.3, 36.5, 32.2, 31.3, 29.9, 29.8, 29.7, 29.6, 29.5, 23.0, 14.4. MALDI–TOF–MS: Calcd.for C 38 h 58 o 2 [M+H] + :m / z=546.88; Found: 546.98.

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Abstract

The invention relates to a crown ether-containing HBC compound and its preparation and application. The general formula of the compound is formula: I or II. Preparation: Suzuki coupling reaction between the substituted hexaphenylbenzene intermediate and the monomer is used to obtain the oxidation precursor, and the precursor is catalyzed by ferric chloride to perform Scholl oxidation ring closure to obtain the target compound. The invention can be used as an excellent self-assembled unit molecule in the fields of biological materials, selective separation materials, chiral response materials and the like; the synthesis of raw materials has the advantages of simple method and mature preparation process, and has good application prospects.

Description

technical field [0001] The invention belongs to the field of supramolecular assembly materials and their preparation and application, in particular to a crown ether-containing HBC compound and its preparation and application. Background technique [0002] Since the concept of supramolecular chemistry was proposed in the 1980s, supramolecular chemistry has experienced rapid development. Among them, supramolecular materials with regular assembly morphology assembled from organic single molecules have become a research hotspot, and their molecular design and material development have attracted the interest of a large number of scientists. Hexa-peri-hexabenzocoronene (HBC) derivatives with large π-conjugated structures are favored, and the solubility and thermal properties of HBC derivatives can be endowed by introducing flexible side chains on the aromatic nucleus , is crucial for molecular synthesis and subsequent application of functional materials. Due to the large π-conju...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D323/00C09K11/06G01N21/64C07C227/40C07C229/00
CPCC07C227/40C07D323/00C09K11/06C09K2211/181G01N21/64C07C229/00
Inventor 张灯青曾旺金武松李贤英刘雨
Owner DONGHUA UNIV
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