A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy
Summary: A novel cyclobutane-containing diacid building block, CBDA-3, was synthesized from sorbic acid using clean, efficient [2 + 2] photocycloaddition. This photoreaction can be performed using commercially available germicidal lamps, which represent a form of ECO-UV. SC-XRD showed that the cyclo...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-09-01
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| Series: | iScience |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2589004222012925 |
| _version_ | 1828177055764709376 |
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| author | Micah Mabin Quintin Elliott Zhihan Wang Angel Ugrinov Qianli R. Chu |
| author_facet | Micah Mabin Quintin Elliott Zhihan Wang Angel Ugrinov Qianli R. Chu |
| author_sort | Micah Mabin |
| collection | DOAJ |
| description | Summary: A novel cyclobutane-containing diacid building block, CBDA-3, was synthesized from sorbic acid using clean, efficient [2 + 2] photocycloaddition. This photoreaction can be performed using commercially available germicidal lamps, which represent a form of ECO-UV. SC-XRD showed that the cyclobutane ring in CBDA-3 has a unique semi-rigid character, unlike more rigid aromatic rings or more flexible types of aliphatic rings. C=C bonds present in the structure of CBDA-3 provide opportunities for derivatization which could be used to alter the characteristics of polymers made from this monomer. Additionally, TGA and DSC analysis showed CBDA-3 to have excellent thermal stability. These characteristics make CBDA-3 a promising building block with the potential to be used as a sustainable alternative to traditional petroleum-derived diacids. Finally, a facile and reliable Fischer esterification of CBDA-3 was performed to tune its melting point and solubility for different applications and to demonstrate the applicability of this building block in polymer synthesis. |
| first_indexed | 2024-04-12T04:53:17Z |
| format | Article |
| id | doaj.art-3157f7d110f449ce967cdbfa4ca0b959 |
| institution | Directory Open Access Journal |
| issn | 2589-0042 |
| language | English |
| last_indexed | 2024-04-12T04:53:17Z |
| publishDate | 2022-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | iScience |
| spelling | doaj.art-3157f7d110f449ce967cdbfa4ca0b9592022-12-22T03:47:13ZengElsevieriScience2589-00422022-09-01259105020A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergyMicah Mabin0Quintin Elliott1Zhihan Wang2Angel Ugrinov3Qianli R. Chu4Department of Chemistry, University of North Dakota, Grand Forks, ND 58202, USADepartment of Chemistry, University of North Dakota, Grand Forks, ND 58202, USADepartment of Chemistry, University of North Dakota, Grand Forks, ND 58202, USADepartment of Chemistry and Biochemistry, North Dakota State University, Fargo, ND 58102, USADepartment of Chemistry, University of North Dakota, Grand Forks, ND 58202, USA; Corresponding authorSummary: A novel cyclobutane-containing diacid building block, CBDA-3, was synthesized from sorbic acid using clean, efficient [2 + 2] photocycloaddition. This photoreaction can be performed using commercially available germicidal lamps, which represent a form of ECO-UV. SC-XRD showed that the cyclobutane ring in CBDA-3 has a unique semi-rigid character, unlike more rigid aromatic rings or more flexible types of aliphatic rings. C=C bonds present in the structure of CBDA-3 provide opportunities for derivatization which could be used to alter the characteristics of polymers made from this monomer. Additionally, TGA and DSC analysis showed CBDA-3 to have excellent thermal stability. These characteristics make CBDA-3 a promising building block with the potential to be used as a sustainable alternative to traditional petroleum-derived diacids. Finally, a facile and reliable Fischer esterification of CBDA-3 was performed to tune its melting point and solubility for different applications and to demonstrate the applicability of this building block in polymer synthesis.http://www.sciencedirect.com/science/article/pii/S2589004222012925Chemistryorganic chemistrygreen chemistry |
| spellingShingle | Micah Mabin Quintin Elliott Zhihan Wang Angel Ugrinov Qianli R. Chu A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy iScience Chemistry organic chemistry green chemistry |
| title | A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy |
| title_full | A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy |
| title_fullStr | A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy |
| title_full_unstemmed | A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy |
| title_short | A biorenewable cyclobutane-containing building block synthesized from sorbic acid using photoenergy |
| title_sort | biorenewable cyclobutane containing building block synthesized from sorbic acid using photoenergy |
| topic | Chemistry organic chemistry green chemistry |
| url | http://www.sciencedirect.com/science/article/pii/S2589004222012925 |
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