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π-extended s-triazepine derivatives and their synthetic methods

A technology of mesitrazine and synthesis method, applied in the field of synthesis of nano-graphene compounds, can solve unfavorable electron transport performance and improvement of device performance, limit conjugation, hinder π-π stacking effect and self-assembly Properties and other issues, to achieve the effect of eliminating adverse effects, improving material properties and device performance, and expanding π-conjugated systems

Inactive Publication Date: 2018-03-06
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This nearly vertical geometric relationship not only restricts the conjugation between the edge aryl groups and the pine core, but also the resulting steric hindrance hinders the π-π stacking and self-assembly properties between PAH molecules, thus It is not conducive to the improvement of the electron transport performance of the material and the performance of the device

Method used

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  • π-extended s-triazepine derivatives and their synthetic methods
  • π-extended s-triazepine derivatives and their synthetic methods
  • π-extended s-triazepine derivatives and their synthetic methods

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Taking the synthesis of π-extended s-triazepine derivatives with the following structural formula as an example, the specific synthesis method is as follows:

[0020]

[0021] Add 0.14g (0.2mmol) 1,5,9-triamino-2,3,6,7,10,11-hexabutoxytriphenylene and 0.15g (1.2mmol) salicylaldehyde to 5mL N-formaldehyde In pyrrolidone (NMP), stir evenly at room temperature, then dropwise add 0.0014g trifluoromethanesulfonic acid, raise the temperature to 120°C, track and detect with TLC, the reaction ends after 12 hours, cool to room temperature, add 0.16g (1.2mmol) Water K 2 CO 3 , heated to 120°C with stirring, cooled to room temperature after 12 hours of reaction, diluted with 20 mL of distilled water, extracted with chloroform (20 mL x 3 times), washed repeatedly with water and saturated saline, and finally the combined organic phase with anhydrous Na 2 SO 4 Dry overnight, concentrate by rotary evaporation, and carry out column chromatography with chloroform, and the obtaine...

Embodiment 2

[0025] Taking the synthesis of π-extended s-triazepine derivatives with the following structural formula as an example, the specific synthesis method is as follows:

[0026]

[0027] The salicylaldehyde used in Example 1 is replaced with equimolar 5-tert-butyl salicylaldehyde, and other steps are the same as in Example 1 to obtain an orange-red solid, i.e., π-extended s-triazepine derivatives, and the yield It is 96%, and the melting point is greater than 300°C.

[0028] The resulting product was characterized with an Avance type superconducting Fourier digital nuclear magnetic resonance spectrometer (Switzerland, Bruker company) and a MALDI-TOF mass spectrometer (Germany, BurkerDaltonics), and the characterization data were as follows:

[0029] 1 H NMR (400MHz, CDCl 3 +TMS)δ(ppm): 8.93(s, 3H), 7.56(dd, J=8.2, 2.4Hz, 3H), 7.13(d, J=8.6Hz, 3H), 4.84(t, J=6.1Hz, 6H), 2.20-2.13(m, 6H), 2.03-1.94(m, 6H), 1.63(s, 27H), 1.20(t, J=7.3Hz, 9H); 13 C NMR (75MHz, CDCl 3 +TMS)δ(ppm)...

Embodiment 3

[0031] Taking the synthesis of π-extended s-triazepine derivatives with the following structural formula as an example, the specific synthesis method is as follows:

[0032]

[0033] The salicylaldehyde used in Example 1 is replaced with equimolar 4-methoxy salicylaldehyde, and other steps are the same as in Example 1 to obtain an orange-red solid, that is, π-extended s-triazepine derivatives, and the yield It is 85%, and the melting point is greater than 300°C.

[0034] The resulting product was characterized with an Avance type superconducting Fourier digital nuclear magnetic resonance spectrometer (Switzerland, Bruker company) and a MALDI-TOF mass spectrometer (Germany, BurkerDaltonics), and the characterization data were as follows:

[0035] 1 H NMR (300MHz, CDCl 3 +TMS) δ (ppm): 8.17 (d, J = 8.6Hz, 3H), 6.68 (d, J = 6.9Hz, 3H), 6.43 (s, 3H), 4.53 (t, J = 6.0Hz, 6H) , 3.87(s, 9H), 1.96-1.89(m, 6H), 1.81-1.74(m, 6H), 1.15(t, J=7.2Hz, 9H); 13 C NMR (75MHz, CDCl 3 +TM...

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Abstract

The invention discloses Pi-extended sym-triazacoronene derivative and a synthetic method thereof. This derivative has a following structural formula, wherein R refers to C1-C10 alkyl, R1, R2 and R3 individually represent any one of H, C1-C4 alkyl, C1-C4 alkoxy, phenyl and C1-C4 alkyl substituted phenyl; 1,5,9-triamine-2,3,6,7,10,11-hexaalkoxybenzphenanthrene and salicylaldehyde or salicylaldehyde derivatives are subjected as raw materials to Pictet-Spengler reaction under acid catalysis and then subjected to intramolecular nucleophilic substitution under alkaline condition to obtain the Pi-extended sym-triazacoronene derivative by one-pot process; reaction conditions are mild, operating is convenient, product yield is high, yield of partial products is up to higher than 90%, and the method is a simple method for synthesizing these compounds.

Description

technical field [0001] The invention belongs to the field of synthesis of nano-graphene compounds, and in particular relates to a synthesis method of a class of triazine compounds and derivatives thereof extended by a π system. Background technique [0002] Polycyclic aromatic hydrocarbons (PAHs) with nano-graphene microstructure can be widely used in organic light-emitting diodes, field-effect transistors, organic photovoltaic cells, and solar cells due to their unique physical and chemical properties and optoelectronic properties. Therefore, the design and synthesis of polycyclic aromatic hydrocarbons with novel structures and better performances has aroused great interest in the scientific and industrial circles. Introducing heteroatoms into the molecular framework of PAHs and expanding their π-conjugated systems is one of the important ways to adjust the physical and chemical properties and photoelectric properties of PAHs. The introduction of heteroatoms can affect the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/22C09K11/06
CPCC07D491/22C09K11/06C09K2211/1088
Inventor 魏俊发刘波李明李靖石先莹杨明瑜施东辉杨奕辉程昆木张强刘恒鲁瑶
Owner SHAANXI NORMAL UNIV
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