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Tetraaryl-substituted bis-phenanthrene-fused compound based on dithienothiophene and preparation

A technology for bisphenanthrene fused dithiophenes and compounds, applied in the field of tetraaryl substitution and bisphenanthrene fused compounds

Inactive Publication Date: 2019-04-05
SICHUAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still a few reports on the expansion of functional materials formed by π-conjugated coplanar surfaces by coupling with aryl groups first and then ring-closing to achieve fusion.

Method used

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  • Tetraaryl-substituted bis-phenanthrene-fused compound based on dithienothiophene and preparation
  • Tetraaryl-substituted bis-phenanthrene-fused compound based on dithienothiophene and preparation
  • Tetraaryl-substituted bis-phenanthrene-fused compound based on dithienothiophene and preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] The compound provided in this example is a compound of general formula (I), wherein R is C n h 2n+1， n represents that the number of carbon atoms is 12, and its preparation process is as follows.

[0068] R is C 12 h 25 Preparation of intermediate B.

[0069] Intermediate B: .

[0070] Starting from 3,4-bis(dodecyloxy)bromobenzene, obtained in any manner, N 2 Under protection, it was mixed with biboronic acid pinacol ester and palladium catalyst ([1, 1']-bis(diphenylphosphino)ferrocenedichloropalladium dichloromethane complex) at 1:1.5:0.05 The molar ratio was added to dimethyl sulfoxide, and reacted at a temperature of 120° C. for 24 hours in the presence of potassium acetate with a molar ratio of 3:1 to the raw material. After the reaction, cool to room temperature, extract with dichloromethane, combine organic phases and dry over anhydrous magnesium sulfate, filter, and spin dry in vacuo; the resulting substance is separated and purified by silica column chro...

Embodiment 2

[0077] The compound provided in this example is a compound of general formula (I), wherein R is C n h 2n+1， n represents that the number of carbon atoms is 16, and its preparation process is as follows.

[0078] R is C 16 h 33 Preparation of intermediate B.

[0079] Intermediate B: .

[0080] Starting from 3,4-bis(hexadecyloxy)bromobenzene, obtained in any way, N 2 Under protection, it was mixed with biboronic acid pinacol ester and palladium catalyst ([1, 1']-bis(diphenylphosphino)ferrocenedichloropalladium dichloromethane complex) at 1:2:0.1 Add the molar ratio of 1,4-dioxane into 1,4-dioxane, and react at a temperature of 80° C. for 36 hours in the presence of potassium acetate with a molar ratio of 3:1 to the raw material. After the reaction, cool to room temperature, extract with dichloromethane, combine organic phases and dry over anhydrous magnesium sulfate, filter, and spin dry in vacuo; the resulting substance is separated and purified by silica column chromat...

Embodiment 3

[0087] The compound provided in this example is a compound of general formula (II), wherein R is C n h 2n+1， n represents that the number of carbon atoms is 12, and its preparation reaction is as follows.

[0088] General formula (Ⅱ): .

[0089] Convert R to C 12 h 25 The compound of general formula (I) was dissolved in dichloromethane, added with R as C 12 h 25 The molar ratio of the compound of general formula (I) to FeCl is 6:1 3 , room temperature reaction 3 ~ 5h. The reaction was quenched with methanol, the mixed solution was washed 3 times with distilled water, and the organic phase was spin-dried in vacuum, recrystallized 3-5 times with toluene to obtain R is C 12 h 25 The octalkoxy-substituted bisphenanthrene fused dithienothiophene compound in the general formula (II), the yield: 79%.

[0090] H NMR spectrum: 1 H NMR (CDCl3, TMS, 400 MHz). δ: 7.55 (s, 4H, ArH), 7.44 (s,2H, ArH), 7.00 (s, 2H, ArH), 4.31 (s, 4H, OCH 2 ), 4.14 (s, 12H, OCH 2 ), 1.95-2.05 (m...

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Abstract

The invention discloses a tetraaryl-substituted bis-phenanthrene-fused compound based on dithienothiophene containing a plurality of alkoxy chains and a synthesis method of the compound, and the compound has the structures shown in general formulas (I) and (II). A polycyclic-fused compound of the bis-phenanthrene-fused dithienothiophene in the general formula (II) can be obtained by intramolecularoxidation ring-closing of FeCl3 of a tetraaryl-substituted dithienothiophene compound in the general formula (I). The tetraaryl-substituted dithienothiophene compound in the general formula (I) has blue fluorescence emission and certain liquid crystal properties. Due to the further expansion of the central conjugated coplanar, the bis-phenanthrene-fused dithienothiophene compound in the general formula (II) can be self-assembled into a stable liquid crystal interphase in a highly ordered manner and is a good mesocrystal. The compound can further be used as an OLED blue luminescent material with higher optical quantum yield, an excellent P-type semiconductor material with high hole transport rate and a gel of multiple polar / non-polar organic solvents.

Description

technical field [0001] The invention relates to a dithienothiophene-based tetraaryl-substituted and bisphenanthrene condensed compound containing eight alkoxy chains and a preparation method thereof. Background technique [0002] At present, many research efforts are focused on extended π-conjugated large planar polyaromatic fused organic materials, mainly because these compounds have large π-electron delocalization area, self-assembly self-healing function and controllable HOMO-LUMO energy gap And other highlights. Its applications include liquid crystal displays, solar cells, field effect transistors, thin film transistors, organic light-emitting diodes, electrical conductors in optoelectronic materials, and organic semiconductors. In addition, large planar π-conjugated arene condensed compounds also have important applications in nonlinear optical materials. [0003] Dithienothiophenes, as a typical polycyclic heterocyclic fused compound, have become one of the most pro...

Claims

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Application Information

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IPC IPC(8): C07D495/14C09K11/06C09K19/34B01J13/00
CPCB01J13/0065C07D495/14C09K11/06C09K19/3491C09K2211/1092
Inventor 马涛赵可清赵可孝
Owner SICHUAN NORMAL UNIVERSITY
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