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Quaterthiophene condensed perylene bisimide derivative and preparation method thereof

A technology of tetrathiophene-fused peryleneimide and thiophene-fused peryleneimide, which is applied in the field of tetrathiophene-fused peryleneimide derivatives and their preparation, and there are few derivatives that can solve nonbay position functionalization Reporting and other issues

Active Publication Date: 2019-11-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0004] Although the method of nonbay functionalization has been discovered and reported as early as 2009, so far there are few reports of nonbay functionalized derivatives

Method used

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  • Quaterthiophene condensed perylene bisimide derivative and preparation method thereof
  • Quaterthiophene condensed perylene bisimide derivative and preparation method thereof
  • Quaterthiophene condensed perylene bisimide derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Example 1, [1,2-b:6,5-b':7,8-b":12,11-b"']tetrathiophene fused peryleneimide derivative C 5,5 -Preparation of PTTI compound (formula Ⅰ-1)

[0101] 1) Preparation of 2,5,8,11-position tetraboronic acid ester substituted perylene imide derivatives (formula IV-1)

[0102]

[0103] Concrete synthetic steps:

[0104] In a 100ml sealed tube, add PDI (500mg, 0.715mmol) of formula Ⅴ-1, pinacol borate (1.45g, 5.723mmol), [Ir(OMe)cod] 2 (14mg, 0.02mmol), tris(pentafluorophenyl)phosphine (47mg, 0.09mmol), vacuumize and fill with argon, add 10ml of dioxane, heat to 110°C for 48h, cool the reaction to room temperature, spin to dry the solvent , silica gel column chromatography (CH 2 Cl 2 ), via CH 2 Cl 2 / MeOH recrystallization to obtain orange-yellow compound formula IV-1 (671 mg, 78%).

[0105] 1 H NMR (CDCl 3 ):δ=0.80(t,12H),1.21(m,32H),1.59(s,48H),1.73-1.78(m,4H),2.09-2.14(m,4H),5.01-4.94(m,2H ), and 8.44(s,4H)ppm; HRMS(MALDI(N),100%):calcd(%)for C 70 h 98 B 4 N ...

Embodiment 2

[0125] Example 2, [1,2-b:6,5-b':7,8-b":12,11-b"']tetrathiophene fused peryleneimide derivative C4F-PTTI compound ( The synthetic route of formula Ⅰ-2):

[0126] 1) Preparation of 2,5,8,11-position tetraboronic acid ester substituted perylene imide derivatives (formula IV-2)

[0127] The reaction equation is as follows, and the specific steps are referring to step 1) of Example 1.

[0128]

[0129]2) Preparation of 2,5,8,11-tetrabromo-substituted perylene imide derivatives (formula III-2)

[0130] The reaction equation is as follows, and the specific steps are referring to step 2) of Example 1.

[0131]

[0132] 3) Preparation of 2,5,8,11-tetrakynyl substituted perylene imide derivatives (Formula II-2)

[0133] The reaction equation is as follows, and the specific steps are referring to step 3 of Example 1).

[0134]

[0135] Characterization parameters:

[0136] 1 H NMR (400MHz, CDCl 3 ): δ=8.60(s, 4H), 5.09-5.02(m, 4H), 1.25-1.24(d, J=4.0Hz, 84H); 13 C NMR (1...

Embodiment 3

[0147] Example 3, [1,2-b:6,5-b':7,8-b":12,11-b"'] tetrathiophene fused perylene imide derivative C 5,5 -Preparation of PTTI-Ph compound (formula Ⅰ-3)

[0148] 1) Preparation of 2,5,8,11-tetraphenylethynyl substituted perylene imide derivatives (Formula II-3)

[0149]

[0150] Concrete synthetic steps:

[0151] Add compound formula III-1 (500mg, 0.493mmol), phenylacetylene (503mg, 4.928mmol), Pd (pph 3 ) 2 Cl 2 (70mg, 0.1mmol), evacuated and filled with argon, added 20ml THF, heated to 40°C for 2h, cooled to room temperature, poured into 500ml water, filtered with suction, dried, and separated by silica gel column chromatography DCM:PE=1: 4. Obtain compound formula II-3 (440 mg, 80%). HRMS(MALDI(N),100%): calcd(%) for C 40 h 70 N 2 o 4 :1250.248; found, 1250.247.

[0152] 2) [1,2-b:6,5-b':7,8-b":12,11-b"'] tetrathiophene fused perylene imide derivatives (formula Ⅰ-3) preparation

[0153] The reaction equation is as follows, and the specific steps are referring to...

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Abstract

The invention relates to a quaterthiophene condensed perylene bisimide derivative and a preparation method thereof. The quaterthiophene condensed perylene bisimide derivative is a [1,2-b:6,5-b':7,8-b'':12,11-b'' '] quaterthiophene condensed perylene bisimide derivative, and a structural formula of the derivative is shown in a formula I (please see the specification for the formula). The preparation method includes the steps that 2,5,8,11-alkyne substituted 3,4:9,10-perylenetetracarboxylic diimide is used as a raw material and heated under protection of inert gas, the sulfur element is introduced through elemental sulfur, and thus the quaterthiophene condensed perylene bisimide derivative as shown in the formula is prepared. The derivative can be used as an organic semiconductor n- type electron transmission material to be applied to organic electroluminescence devices, organic thermochromism elements, organic field effect transistors, organic solar cells and the like, and also can be used as an intermediate for preparing novel perylene bisimide electron acceptor materials.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a tetrathiophene-fused peryleneimide derivative and a preparation method thereof. Background technique [0002] Perylene imide (PDI) consists of two units of perylene and strong electron-withdrawing imide of fused ring aromatic hydrocarbons. The core of perylene imide has eight reactive sites, and the ortho position of the imide substituent is It is called nonbay position or alpha position (2,5,8,11-position), and the meta-position of imide substituent is called bay position or beta position (1,6,7,12-position). From the frontier orbitals (HOMO and LUMO) of perylene imide, it can be seen that the substituents on the PDI nitrogen atom have little effect on the HOMO and LUMO of the molecule, while the changes of the substituents on the eight side positions can regulate the HOMO and LUMO. LUMO energy level, thereby changing its electrochemical propert...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22
CPCC07D495/22
Inventor 王朝晖曾成姜玮
Owner INST OF CHEM CHINESE ACAD OF SCI
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