Towards an operationally practical synthesis of benzene-1,2,4,5-tetracarbaldehyde : – a key building block for proposed electro-responsive materials
(2023) KEML10 20231Department of Chemistry
- Abstract
- Introduction: Electro-responsive materials have many applications such as electronic devices, actuators, and artificial muscles.
Background: When an electric field is applied to electro-responsive materials, they can change in size, shape, or conformation.
Aim: The aim of this thesis is to develop an operationally practical synthesis of a key building block in a proposed electro-responsive material. This building block is benzene-1,2,4,5-tetracarbaldehyde (1). Important parameters for the practicality of the synthesis are high yield, low cost, and low environmental impact.
Methods: Two oxidation pathways were evaluated, and the second pathway was optimized by changing factors such as solvent, reaction time, temperature, concentration,... (More) - Introduction: Electro-responsive materials have many applications such as electronic devices, actuators, and artificial muscles.
Background: When an electric field is applied to electro-responsive materials, they can change in size, shape, or conformation.
Aim: The aim of this thesis is to develop an operationally practical synthesis of a key building block in a proposed electro-responsive material. This building block is benzene-1,2,4,5-tetracarbaldehyde (1). Important parameters for the practicality of the synthesis are high yield, low cost, and low environmental impact.
Methods: Two oxidation pathways were evaluated, and the second pathway was optimized by changing factors such as solvent, reaction time, temperature, concentration, and equivalents of reagent. The results were quantified by 1H NMR spectroscopy.
Results: The yields were <5%, which means that they are not synthetically useful at this point. In the optimization, no key parameter was identified that could be varied to improve the yields significantly, as only small improvements were seen. The critical issue appears to be the oxidation of the aldehydes to the carboxylic acid stage.
Conclusion: Benzene-1,2,4,5-tetracarbaldehyde (1) was not isolated and the oxidations were proven to be complicated due to high reactivity leading to over-oxidation. The reactions were however not proven impossible. Benzene-1,2,4,5-tetracarboxylic acid (3) and 1,2,4,5-tetramethyl-benzene (durene, 4) are two cheap starting materials and the oxidation methods evaluated were comparatively less toxic and less environmentally hazardous compared to commonly used Swern and pyridinium chlorochromate (PCC) oxidation. (Less) - Popular Abstract
- The use of electronic equipment has increased rapidly since the first electric battery was developed in the 1800s. Electronic devices such as computers, smartphones, and medical devices are used every day, and as our need for electronic equipment evolves, the devices need to follow. A switch is an electronic device, that controls an electric circuit by switching it between on and off states. The process of making components smaller is called miniaturization, and miniaturization of devices has been shown to increase speed and decrease energy consumption. Problems that emerged in the early 2000s included heat buildup and quantum effects leading to electron unpredictability. One solution could be to shift the focus from silicon dioxide, which... (More)
- The use of electronic equipment has increased rapidly since the first electric battery was developed in the 1800s. Electronic devices such as computers, smartphones, and medical devices are used every day, and as our need for electronic equipment evolves, the devices need to follow. A switch is an electronic device, that controls an electric circuit by switching it between on and off states. The process of making components smaller is called miniaturization, and miniaturization of devices has been shown to increase speed and decrease energy consumption. Problems that emerged in the early 2000s included heat buildup and quantum effects leading to electron unpredictability. One solution could be to shift the focus from silicon dioxide, which is the most commonly used material in transistors today, to other materials. The aim of the study is to synthesize an intermediate compound, benzene-1,2,4,5-tetracarbaldehyde (1), in a proposed synthesis of dibisbenzo[a,e]cyclooctatetraene (dbbCOT, 2), which has potential to be used as an electro-responsive material. Multiple pathways for the synthesis of this compound have been explored. The pathways are promising but no conditions were found to achieve yields that are synthetically useful. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/9136428
- author
- Sundman, Tanja LU
- supervisor
- organization
- course
- KEML10 20231
- year
- 2023
- type
- M2 - Bachelor Degree
- subject
- keywords
- cyclooctatetraene, benzene-1 2 4 5-tetracarbaldehyde, switchable hydrocarbon, electro-responsive materials, oxidation, organic chemistry
- language
- English
- id
- 9136428
- date added to LUP
- 2023-09-15 11:56:56
- date last changed
- 2023-09-15 11:56:56
@misc{9136428,
abstract = {{Introduction: Electro-responsive materials have many applications such as electronic devices, actuators, and artificial muscles.
Background: When an electric field is applied to electro-responsive materials, they can change in size, shape, or conformation.
Aim: The aim of this thesis is to develop an operationally practical synthesis of a key building block in a proposed electro-responsive material. This building block is benzene-1,2,4,5-tetracarbaldehyde (1). Important parameters for the practicality of the synthesis are high yield, low cost, and low environmental impact.
Methods: Two oxidation pathways were evaluated, and the second pathway was optimized by changing factors such as solvent, reaction time, temperature, concentration, and equivalents of reagent. The results were quantified by 1H NMR spectroscopy.
Results: The yields were <5%, which means that they are not synthetically useful at this point. In the optimization, no key parameter was identified that could be varied to improve the yields significantly, as only small improvements were seen. The critical issue appears to be the oxidation of the aldehydes to the carboxylic acid stage.
Conclusion: Benzene-1,2,4,5-tetracarbaldehyde (1) was not isolated and the oxidations were proven to be complicated due to high reactivity leading to over-oxidation. The reactions were however not proven impossible. Benzene-1,2,4,5-tetracarboxylic acid (3) and 1,2,4,5-tetramethyl-benzene (durene, 4) are two cheap starting materials and the oxidation methods evaluated were comparatively less toxic and less environmentally hazardous compared to commonly used Swern and pyridinium chlorochromate (PCC) oxidation.}},
author = {{Sundman, Tanja}},
language = {{eng}},
note = {{Student Paper}},
title = {{Towards an operationally practical synthesis of benzene-1,2,4,5-tetracarbaldehyde : – a key building block for proposed electro-responsive materials}},
year = {{2023}},
}