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Propellane derivatives based on perylene bisimide C3 symmetry, and synthesis and application thereof

A technology of perylene imide and spirane, which is applied to the spirane derivatives based on perylene imide C3 symmetry and their synthesis and application fields, can solve the problems of low charge conversion efficiency, electronic structure, and aggregated state optoelectronic materials. Performance is less well known and other issues

Active Publication Date: 2018-12-14
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, peryleneimide compounds with a two-dimensional structure have large intermolecular forces and are easy to crystallize and assemble. Such compounds usually have high electron transport efficiency, and as acceptor materials for batteries, their charge conversion efficiency relatively low
However, there are relatively few studies on peryleneimide derivatives with three-dimensional structures, and their electronic structures, aggregation states, and properties as optoelectronic materials are rarely known.

Method used

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  • Propellane derivatives based on perylene bisimide C3 symmetry, and synthesis and application thereof
  • Propellane derivatives based on perylene bisimide C3 symmetry, and synthesis and application thereof
  • Propellane derivatives based on perylene bisimide C3 symmetry, and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of compound 2a

[0044] Compound 1a (100mg, 69.27mmol) and 100mL chloroform solvent were added into a two-necked flask. After heating to reflux, bromine (0.97g, over 120eq.) was added slowly. Reflux for 6 hours, cool, the reaction solution was extracted with saturated aqueous sodium sulfite, and the solvent was removed after drying. The remaining residue was purified and separated on a silica gel column, and the developing solvent was petroleum ether / chloroform (1:1 to 3:1, v / v ) to obtain purple-red compound 2a (60 mg, 45%).

[0045] Bromine is used as a bromination reagent, and the bromination reagent can also be other commonly used bromination reagents, but the effect is different, and the effect of bromine is verified through experiments.

[0046]

[0047] 2a: 1 H NMR (400MHz, CDCl 3 ,300K)δ9.57(d,J=8.0Hz,6H),8.80(s,6H),8.33(d,J=8.0Hz,6H),5.17-5.09(m,3H),2.26-2.16(m ,6H),1.86-1.76(m,6H),1.32-1.20(m,36H),0.81(t,J=6.5Hz,18H);

[0048] 13 C NMR (126...

Embodiment 2

[0062] Synthesis of compound 3a

[0063] Compound 2a (80mg, 0.04mmol), 4-tert-butylphenylboronic acid (9eq., 64.12mg, 0.36mmol) and tetrakis(triphenylphosphine)palladium (30%eq., 13.85mg, 0.01mmol) were added to In a Shrek bottle filled with nitrogen, tetrahydrofuran (20 mL) and 2M potassium carbonate aqueous solution (10 mL) were added sequentially. The reaction solution was heated to 55°C for 12 hours, then the water phase was removed with a separatory funnel to retain the organic phase, the solvent was evaporated to dryness under reduced pressure, the filter residue was washed with methanol and dried. The dried crude product was further purified using a silica gel column to obtain the purple product 3a (53 mg, 59%), and the entire post-treatment process needs to be protected from light.

[0064]

[0065] 3a: 1 H NMR (500MHz, CDCl 2 CDCl 2 ,373K)δ=8.41(s,6H),7.80(d,J=8.1Hz,6H),7.56(d,J=8.1Hz,12H),7.40(dd,J=7.8,5.4Hz,18H), 5.18-5.14(m,3H),2.28-2.21(m,6H),1.93-1.88(m,6...

Embodiment 3

[0069] Synthesis of Compound 4a

[0070] In a standard photochemical reaction tube, compound 3a (2×40 mg, 35.77 mmol), toluene (2×40 mL) and iodine (5 mg) were added. The reaction solution was irradiated under blue light (460-465 nm) at 95° C. for 12 hours. Then, the reaction solution was extracted with saturated aqueous sodium sulfite solution, and then the aqueous phase was removed with a separatory funnel to retain the organic phase. The solvent was evaporated to dryness under reduced pressure, and the filter residue was washed with methanol and dried. The dried crude product was further purified by silica gel column (PE:DCM=2:1, v:v) to obtain yellow compound 4a (60 mg, 75%).

[0071]

[0072] 4a: 1 H NMR (400MHz, CDCl 3 ,300K)δ=10.90(s,6H),10.54(d,J=15.1Hz,6H),9.96(s,6H),9.53(d,J=8.8Hz,6H),8.32(d,J=8.7 Hz,6H),5.49-5.42(m,3H),2.47-2.37(m,6H),2.14-1.87(m,60H),1.34-1.18(m,36H),0.83-0.74(m,18H);

[0073] 13 C NMR (125MHz, CDCl 2 CDCl 2 ,373K):δ=166.38,152.24,147.07...

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Abstract

The invention provides propellane derivatives based on perylene bisimide C3 symmetry, and synthesis and application thereof. The structural formula of the propellane derivatives is as shown in a formula 2 which is described in the specification. The group X in the formula 2 is selected from groups as described in the specification. The invention discloses a series of the propellane derivatives based on perylene bisimide C3 symmetry and synthesized for the first time. According to the invention, a ring structure is introduced between two naphthalene rings in perylene on the basis of a compound1 to further enlarge a conjugated Pi system so as to obtain more excellent electron transmission efficiency.

Description

technical field [0001] The invention relates to the technical field of organic materials, in particular to a perylene imide C 3 Symmetrical Spiralane Derivatives and Their Synthesis and Applications. Background technique [0002] C 3 Symmetrical three-dimensional materials have recently attracted much attention due to their significance in sensors, photoelectric conversion, energy storage, and supramolecular self-assembly. A notable feature of this type of material is that the molecular structure contains three structural units that are 120° to each other, so this type of molecule generally has a large intramolecular free volume (intramolecular free volume), which is ideal for preparing molecular cages and two-dimensional polymers. (2D polymers) important structural unit. Such compounds with unique structures usually contain more active sites. Appropriate chemical modification of the active sites of the compounds can endow the compounds with some special properties. For ...

Claims

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Application Information

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IPC IPC(8): C07D471/20C07F7/08C09K11/06H01L51/30H01L51/46H01L51/54
CPCC09K11/06C07D471/20C07F7/0814C09K2211/1092C09K2211/1029C09K2211/1007H10K85/655H10K85/6572H10K85/657H10K85/40
Inventor 张磊吕玲玲贾珍梅
Owner BEIJING UNIV OF CHEM TECH
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