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All-alkyl substituted triindene cyclotrimeric indole derivatives and preparation method thereof

A technology for alkylation of trimerindole and trimerindole, which is applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve problems such as limited research and difficult synthesis

Inactive Publication Date: 2011-12-28
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current research on it is very limited due to the difficulty in its synthesis

Method used

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  • All-alkyl substituted triindene cyclotrimeric indole derivatives and preparation method thereof
  • All-alkyl substituted triindene cyclotrimeric indole derivatives and preparation method thereof
  • All-alkyl substituted triindene cyclotrimeric indole derivatives and preparation method thereof

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Embodiment

[0038] Isatin-3-hydrazone (1) preparation of

[0039] Isatin (25.00 g, 170.00 mmol) was dissolved in 200 ml of methanol, 85% hydrazine hydrate (19.40 g, 85%, 515 mmol) was added, heated to reflux for 60 minutes and then cooled, the precipitated solid was suction filtered and dried to obtain yellow Solid (25.15 g, 91.2 %). M.p.: 225°C (decomposition); literature value: 215-219°C.

[0040] 1H-indol-2-one (2) preparation of

[0041] Add sodium ethoxide solution (10.00 g sodium, 250 ml absolute ethanol) dropwise into solid isatin-3-hydrazone (1) (25.00 g, 155.13 mmol), after heating to reflux for 4 hours, the reaction solution was poured into water, extracted with dichloromethane to obtain an organic phase, washed with water, dried with anhydrous magnesium sulfate, spin-dried, and washed with absolute ethanol / petroleum Ether was recrystallized and sucked dry to obtain a white solid (12.40 g, 60.7 %). M.p.: 121-123°C; literature value: 125-127°C.

[0042] trimindole (3) prepa...

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Abstract

The invention discloses an all-alkyl substituted triindenyl-looped trimeric-indole derivative, which is characterized in that indene and trimeric indole are linked to form a star-shaped highly-symmetrical trimeric-indole derivative with a larger conjugated system; and the trimeric-indole derivative belongs to the technical field of organic electroluminescent materials. The invention also relates to a preparation method of the all-ethyl substituted triindenyl-looped trimeric-indole derivative, which comprises the following steps of: by using isatin as a raw material, introducing three n-hexylsto 5, 10 and 15 bits to improve the dissolvability of the trimeric indole after synthesizing the trimeric indole as an intermediate, then introducing three 2-iodophenyl formoxyls to 3, 8 and 13 bits through Friedel-Crafts acylation reaction, then synthesizing a triindone-looped trimeric-indole derivative by utilizing intramolecular palladium-catalyzed C-H aryl-coupling reaction, and then reducingand alkylating to obtain the all-alkyl substituted triindenyl-looped trimeric-indole derivative. A new path is provided for exploring novel organic electroluminescent materials by the compound disclosed by the invention.

Description

technical field [0001] The invention relates to the field of novel organic electroluminescence materials, in particular to a kind of all-ethyl substituted triindene ring and trimerindole derivatives and a preparation method thereof. Background technique [0002] In recent years, organic optoelectronic functional materials have increasingly shown broad prospects and unique characteristics, such as their flexibility and easy regulation between structure and performance. Preparation of devices and materials with excellent photoelectric properties has become a research hotspot in materials chemistry in the 21st century. Hyperbranched organic small molecule compounds (especially organic small molecule compounds with strong symmetry) have received extensive attention, and their multi-directional charge transfer characteristics often endow the compounds with some special photofunctional properties. [0003] It has been reported in the literature that a variety of derivatives of 2,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14C09K11/06
Inventor 刘乾才刘亮
Owner EAST CHINA NORMAL UNIV
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