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Azobenzene derivative, solar thermal energy fuel film composite material and preparation method and application thereof

A technology of azobenzene derivatives and hydroxymethyl azobenzene is applied in the fields of processing and molding to prepare solar thermal fuel film composite materials, photothermal energy storage and solar energy utilization, and can solve the problems of inconvenient use, short energy storage life, and storage problems. For problems such as low energy capacity, it achieves the effects of fast response, good mechanical flexibility and rich sources

Active Publication Date: 2021-03-26
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the prior art, it is reported that azobenzene-based photoresponsive materials are usually in a solid state, such as azobenzene materials containing graphene structures and corrole, which use There is inconvenience, CN111004146A discloses a liquid azophenyl "molecular solar thermal energy fuel" 4-bromobutoxy-2', 6'-diethylazobenzene, its melting point is -18.73 ° C, at normal temperature It is in a liquid state and can be used as a solvent-free solar thermal energy storage material. It is convenient to use, but when the product isomerization rate is 88%, the energy storage capacity is 96.65J / g, and the complete energy storage capacity of the product is 42.8KJ / mol. The energy storage capacity is not high, and the energy storage life is short

Method used

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  • Azobenzene derivative, solar thermal energy fuel film composite material and preparation method and application thereof
  • Azobenzene derivative, solar thermal energy fuel film composite material and preparation method and application thereof
  • Azobenzene derivative, solar thermal energy fuel film composite material and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The preparation of embodiment 1 p-hydroxymethyl azobenzene

[0047] Mix p-methylaniline (10mmol, 1equiv) and high-concentration hydrochloric acid (37%, 2.5mL) in a 100mL round bottom flask, then add distilled water (10mL), put the round bottom flask into ice water and stir. Weigh NaNO 2 (690mg, 10mmol, 1equiv) was put into a 50mL beaker, and 1.5mL of distilled water was added to dissolve it, and then the solution was slowly poured into the above-mentioned round bottom flask and stirred for 4h. Then weigh phenol (940mg, 10mmol, 1equiv), Na 2 CO 3 (1.092mg, 10.3mmol, 1.03equiv) and sodium hydroxide (400mg, 10mmol, 1equiv) in a 50mL beaker, add 10mL of distilled water to dissolve, then add drop by drop in the round bottom flask, and stir at room temperature for 4 Hour. After adjusting the pH to 7 with hydrochloric acid, the precipitated product was filtered off, washed with water (3×20 mL), and dried under vacuum at room temperature for 24 hours. Then put the dried so...

Embodiment 2

[0048] Example 2 1-(4-(isoamyloxy)phenyl)-2-(p-tolyl)diazene (C 18 h 22 N 2 O) Preparation

[0049]

[0050] Weigh p-hydroxymethylazobenzene (1060mg, 5mmol, 1equiv), 1-bromo-3-methylbutane (2266mg, 15mmol, 3equiv) and sodium hydroxide (400mg, 10mmol, 2equiv) in a 100mL round bottom flask , and then add 45mL of absolute ethanol and 5mL of distilled water to it, then put the round bottom flask into an oil bath and heat it to 70°C, circulate the condensed water, and stir for 24h. Then add an appropriate amount of silica gel and rotary steam to form a solid, put it into a chromatography column, use dichloromethane:petroleum ether=1:3 to pass through the product point, and rotary steam to obtain 1-(4-(isoamyloxy)phenyl) -2-(p-Tolyl)diazene, yield 71%, MS (m / z) 282.1. 1 H NMR (500MHz, CDCl 3 ,δ):7.91-7.87(d,2H,Ar-H),7.81-7.77(d,2H,Ar-H),7.32-7.28(d,2H,Ar-H),7.02-6.98(d,2H ,Ar-H),4.09-4.05(t,2H,O-CH 2 ),2.44-2.41(s,3H,-CH 3 ),1.91-1.79(m,1H,-CH),1.75-1.69(q,2H,-CH 2 ),1.0...

Embodiment 3

[0051] Example 3 1-(4-(2-methylbutoxy)phenyl)-2-(p-tolyl)diazene (C 18 h 22 N 2 O) Preparation

[0052]

[0053] Weigh p-hydroxymethylazobenzene (1060mg, 5mmol, 1equiv), 1-bromo-2-methylbutane (2266mg, 15mmol, 3equiv) and sodium hydroxide (400mg, 10mmol, 2equiv) in a 100mL round bottom flask Add 45mL of absolute ethanol and 5mL of distilled water to it, then put the round bottom flask into an oil bath and heat it to 70°C, circulate the condensed water, and stir for 24h. Then add an appropriate amount of silica gel and rotary steam to form a solid, put it into a chromatography column, pass through the product point, and rotary steam to obtain 1-(4-(2-methylbutoxy)phenyl)-2-(p-tolyl) Diazene, yield 63%, MS (m / z) 282.1.

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Abstract

The invention relates to an azobenzene derivative, a solar thermal energy fuel film composite material and a preparation method and application thereof, discloses a series of azobenzene derivatives, and provides a method for preparing a photo-induced phase change ready-to-use solar thermal energy fuel film through the azobenzene derivatives. The prepared solar thermal energy fuel composite film has good mechanical flexibility, photoisomerization effect and energy storage capacity. The composite film can rapidly generate cis-trans isomerization to store energy under the irradiation of an ultraviolet lamp, the stored energy is gradually increased along with the prolonging of irradiation time, the full state can be achieved within about 2 hours, the energy density can reach 200 J / g or above,and the temperature of the composite film can be continuously increased by about 5 DEG C. The charging / discharging process has very good reversibility, and no obvious attenuation exists after the energy is circularly charged / discharged for more than 5 times. The composite material has the advantages of simple preparation process, environmental friendliness, easily available materials, large heat release amount, good mechanical flexibility, strong acid and alkali corrosion resistance, good recycling performance and the like.

Description

technical field [0001] The invention belongs to the field of clean energy and renewable energy, and mainly relates to the design and synthesis of photoresponsive materials, a method for processing and molding solar thermal fuel film composite materials, and applications for photothermal energy storage and solar energy utilization. Background technique [0002] In recent years, the world is facing an energy crisis, and the extensive use of fossil fuels has also caused environmental pollution. The search for new renewable clean energy has become the focus of people. Since the beginning of the 21st century, with the continuous development of solar resource utilization and people's strong demand for clean energy, light-responsive solar thermal fuels have become the focus of research in the field of clean energy. Solar thermal fuel, as a new type of energy storage device, converts solar energy into chemical energy stored in the form of molecular isomers such as cis / trans azobenze...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08F24S60/10
CPCC07C245/08F24S60/10Y02E10/40
Inventor 赵瑞阳李永仓韩吉姝傅云磊穆家慧宋修艳刘福胜
Owner QINGDAO UNIV OF SCI & TECH
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