Synthesis of Unzipping Polyester and a Study of its Photochemistry

Preparation of an unzipping polyester is reported. The monomer was prepared from benzoic acid in a four-step sequence. Step growth polymerization of the monomer provides the target polymer. Efficient depolymerization upon irradiation at 254 nm was confirmed with a quantum yield of >0.8. The photo...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 37; pp. 14736 - 14741
Main Authors Joo, Wontae, Wang, Wade, Mesch, Ryan, Matsuzawa, Kensuke, Liu, Di, Willson, C. Grant
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.09.2019
Amer Chemical Soc
Subjects
aromatization
benzoic acid
Chemistry
Chemistry, Multidisciplinary
depolymerization
homolytic cleavage
irradiation
photolysis
Physical Sciences
polyesters
polymerization
Science & Technology
ultraviolet radiation
DEPOLYMERIZATION
POLYMERS
CASCADE
RELEASE
PRODRUG
CHEMICAL AMPLIFICATION
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ISSN0002-7863
1520-5126
1520-5126
DOI10.1021/jacs.9b06285

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Summary:Preparation of an unzipping polyester is reported. The monomer was prepared from benzoic acid in a four-step sequence. Step growth polymerization of the monomer provides the target polymer. Efficient depolymerization upon irradiation at 254 nm was confirmed with a quantum yield of >0.8. The photolysis mechanism was investigated, and the results of radical trapping experiments are consistent with an initial Norrish type I like homolysis followed by a radical mediated depropagation reaction driven by aromatization.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.9b06285