Azobenzene-based photothermal energy storage molecule, method for preparing the same and use thereof

Patent metadata

Field	Value
Publication number	US-10160720-B1
Application number	US-201816123405-A
Country	US
Kind code	B1
Filing date	Sep 6, 2018
Priority date	Apr 13, 2018
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

Provided is an azobenzene-based photothermal energy storage molecule represented by Formula I which contains two types of azobenzene unit: two biscarboxyl azobenzene units and one monoamino azobenzene unit. By utilizing the energy difference between the two configurations of the azobenzene units, energy is stored during the transition from trans to cis, and in reverse, energy is released. The carboxyl and amino groups on different azobenzene units can form strong intermolecular and intramolecular hydrogen bonds, which leads to a great improvement in energy density and reversion half-life compared with the traditional azobenzene materials in which a single type of an azobenzene unit is grafted. Moreover, the release of thermal energy can be controlled by light and heating, which is beneficial to fully utilize the solar energy for photothermal energy conversion and storage, and used as a solar thermal fuel to the field of heating technology and new generation of light-driven spacecrafts.

First claim

The invention claimed is:

1. An azobenzene-based photothermal energy storage molecule having a structure represented by Formula I:

2. A method for preparing the azobenzene-based photothermal energy storage molecule according to claim 1 , comprising:
subjecting trimethyl 1,3,5-benzenetricarboxylate to a hydrolysis reaction to obtain an intermediate represented by Formula II;
activating the intermediate represented by Formula II with oxalyl chloride, and then reacting with Disperse Orange 3 to obtain an intermediate represented by Formula III;
subjecting the intermediate represented by Formula III to a hydrolysis reaction to obtain an intermediate represented by Formula IV;
activating the intermediate represented by Formula IV with oxalyl chloride, and then reacting with biscarboxyl azobenzene to obtain an intermediate represented by Formula V; and
reacting the intermediate represented by Formula V with Na 2 S to obtain the azobenzene-based photothermal energy storage molecule represented by Formula I;

3. The method according to claim 2 , wherein the subjecting trimethyl 1,3,5-benzenetricarboxylate to a hydrolysis reaction is:
subjecting trimethyl 1,3,5-benzenetricarboxylate to a hydrolysis reaction under an alkaline condition, followed by acidification.

4. The method according to claim 3 , wherein the alkaline condition is provided by an alkaline compound, and the molar ratio of the alkaline compound to trimethyl 1,3,5-benzenetricarboxylate is (1˜1.2): 1.

5. The method according to claim 2 , wherein the subjecting the intermediate represented by Formula III to a hydrolysis reaction is:
subjecting the intermediate represented by Formula III to a hydrolysis reaction under an alkaline condition, followed by acidification.

6. The method according to claim 5 , wherein the alkaline condition is provided by an alkaline compound, and the molar ratio of the alkaline compound to the intermediate represented by Formula III is (2˜2.4): 1.

7. A method of using the azobenzene-based photothermal energy storage molecule according to claim 1 as a solar thermal fuel, comprising applying the azobenzene-based photothermal energy storage molecule to the solar thermal fuel.

8. The method according to claim 7 , wherein the solar thermal fuel is used in the field of heating technology and light-driven spacecrafts.

9. A method of using the azobenzene-based photothermal energy storage molecule produced by the method according to claim 2 as a solar thermal fuel, comprising applying the azobenzene-based photothermal energy storage molecule to the solar thermal fuel.

10. The method according to claim 9 , wherein the solar thermal fuel is used in the field of heating technology and light-driven spacecrafts.

Assignees

• Univ Tianjin

Inventors

• Feng Wei
• Zhai Fei
• Feng Yiyu
• Yang Weixiang
• Dong Liqi

Classifications

• C07C245/08 Primary

  with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene · CPC title

• F24S60/20

  using chemical reactions, e.g. thermochemical reactions or isomerisation reactions · CPC title

• C07C67/313

  by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups · CPC title

• C09K8/08

  containing natural organic compounds, e.g. polysaccharides, or derivatives thereof · CPC title

• Y02E10/40

  Solar thermal energy, e.g. solar towers · CPC title