Synthesis of maleimidotriethoxy silane-series compounds, and preparation method of self-assembled film

A technology of maleimidotriethoxysilane and its synthesis method, which is applied in the fields of chemical instruments and methods, compounds of Group 4/14 elements of the periodic table, organic chemistry, etc., and can solve the problem of catalytic yield and repeatability Poor and other issues

Active Publication Date: 2015-12-09
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But because amino group can make Karstedt catalyst poisoning, so Karstedt catalyst is bad (N.Sabourault, G.Mignani, A.Wagner, C.Mioskowski) for the catalyzed yield and the reproducibility of some olefin compound hydrosilylation reactions with amino groups , Org. Lett., 2002, 13, 2117-2119.)

Method used

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  • Synthesis of maleimidotriethoxy silane-series compounds, and preparation method of self-assembled film
  • Synthesis of maleimidotriethoxy silane-series compounds, and preparation method of self-assembled film
  • Synthesis of maleimidotriethoxy silane-series compounds, and preparation method of self-assembled film

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Synthesis of self-assembly material 11-maleimidoundecyltriethoxysilane.

[0027]

[0028] Synthesis of 10-undecylenamide:

[0029]

[0030] Take urea (15g, 0.25mol) and undecylenic acid (23.01g, 0.125mol) in a two-necked flask, raise the temperature to 170-180°C, and stop heating after 4 hours of reaction. When the temperature drops to 110-120°C, add 5% Na 2 CO 3 The solution (100-150ml) was used to stop the reaction, and the mixture was placed in an ice-water bath, filtered after solid precipitation, recrystallized twice with 95% ethanol, and vacuum-dried to obtain a colorless solid with a yield of 60%. 1 HNMR (400MHz; CDCl 3 ): δ5.80 (1H, m), 5.47 (2H, s), 2.22 (2H, t), 2.04 (2H, m), 1.63 (2H, m), 1.38-1.29 (10H, m).

[0031] Synthesis of 11-amino-1-undecene:

[0032]

[0033] Take LiAlH 4 (2.3g, 60.6mmol), 50ml of dry THF in a 250ml two-necked flask, protected by nitrogen, heated to reflux for 30min and then stopped heating. Compound 10-undecylena...

Embodiment 2

[0041] (1) Preparation of self-assembled membrane

[0042] Step 1: Wash the silicon wafer with a size of 1cm×1cm with a neutral detergent and wash it with a large amount of ultrapure water;

[0043] Step 2: Sonicate silicon wafers with acetone, ethanol, and ultrapure water for 10 minutes in sequence and use N 2 blow dry;

[0044] Step 3: Incorporate the cleaned Si / SiO 2 The substrate is immersed in the piranha solution (H 2 SO 4(conc.) / H 2 o 2(30％) =5:1) for 24h to form hydroxyl groups on its surface;

[0045] Step 4: Dip the activated silicon wafer in 10ml of toluene (dry) solution of 11-maleimidoundecyltriethoxysilane (10 -3 M), N 2 protected, heated to 75°C, and self-assembled for 48h, the Si / SiO 2 A self-assembled film of 11-maleimido undecyltriethoxysilane is self-assembled on a substrate.

[0046] (2) Characterization of materials

[0047] (a) X-ray photoelectron spectroscopy (XPS)

[0048] figure 2 It is the XPS schematic diagram of N1s. The peak with bin...

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Abstract

Among various factors influencing performances of organic electronic components, interfacial property is the most important one influencing the performance of the whole component. In the invention, a series of maleimidotriethoxy silane-series compounds are synthesized, wherein a monomolecular film layer is formed on a surface of an oxide substrate through a self-assembling method, thereby modifying the substrate. Dicyclopentadiene platinum chloride is employed as a catalyst to perform hydrosilylation. Nuclear magnetism is carried out for representation. A test result proves that the catalyst allows catalytic addition to a compound having an amino group to be carried out high-efficiently, and furthermore, silicone on a silanoethoxyl group is connected to a position of a terminal group of a double bond before addition. A self-assembling method is utilized to form the monomolecular film layer on the surface of the oxide substrate. A Young contact angle instrument and XPS is employed for representation, which proves that a flat monomolecular film layer is formed on the surface of the oxide substrate.

Description

technical field [0001] The invention uses a series of triethoxysilane compounds to form a monomolecular film on the surface of an oxide substrate by self-assembly, thereby realizing the modification of the substrate. Background technique [0002] Among the many factors affecting the performance of organic electronic devices, the interface properties have a crucial impact on the performance of the entire device. Because the interface properties affect the growth of organic materials, resulting in changes in the microstructure of thin films, and ultimately affect the performance of organic electronic devices, so the modification of substrates with organic film materials has become an important means to improve interface properties. The organic material commonly used to modify oxide substrates is alkylsilane RSi(OEt) 3 , modified substrates have been widely used in the field of devices (N. Herzer, S. Hoeppener, U.S. Schubert, Chem. Commun. 2010, 46, 5634-5652.). One advantage...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
Inventor 高德青郑朝月陈乃武朱杰黄维
Owner NANJING UNIV OF TECH
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