Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in Polycarbonate

Photodegradation of polycarbonate (PC) is investigated based on quantum chemical methods with PC models to clarify the effect of substituents at different positions of phenyl rings on the carbonate O-C bond cleavage. Compared to the results without substituents on phenyl rings, the breakage of the c...

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Main Authors: Xiao Huang, Yuuichi Orimoto, Yuriko Aoki
Format: Article
Language:English
Published: MDPI AG 2025-04-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/30/8/1839
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author Xiao Huang
Yuuichi Orimoto
Yuriko Aoki
author_facet Xiao Huang
Yuuichi Orimoto
Yuriko Aoki
author_sort Xiao Huang
collection DOAJ
description Photodegradation of polycarbonate (PC) is investigated based on quantum chemical methods with PC models to clarify the effect of substituents at different positions of phenyl rings on the carbonate O-C bond cleavage. Compared to the results without substituents on phenyl rings, the breakage of the carbonate O-C bond is promoted or suppressed when the electron-donating or electron-withdrawing group is placed on the <i>meta</i>- or <i>ortho</i>-positions of the <i>gem</i>-dimethyl groups of phenyl rings, respectively. Moreover, the promotion and suppression of carbonate O-C bond scission are more significant if the substituents are located on the <i>ortho</i>-positions of the <i>gem</i>-dimethyl groups.
format Article
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publishDate 2025-04-01
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series Molecules
spelling doaj-art-aafdc3f08a0b43e693b5a90468ffc3b32025-08-20T02:18:15ZengMDPI AGMolecules1420-30492025-04-01308183910.3390/molecules30081839Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in PolycarbonateXiao Huang0Yuuichi Orimoto1Yuriko Aoki2Department of Interdisciplinary Engineering Sciences, Chemistry and Materials Science, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga Park, Fukuoka 816-8580, JapanDepartment of Material Sciences, Faculty of Engineering Sciences, Kyushu University, 6-1 Kasuga Park, Fukuoka 816-8580, JapanDepartment of Interdisciplinary Engineering Sciences, Chemistry and Materials Science, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga Park, Fukuoka 816-8580, JapanPhotodegradation of polycarbonate (PC) is investigated based on quantum chemical methods with PC models to clarify the effect of substituents at different positions of phenyl rings on the carbonate O-C bond cleavage. Compared to the results without substituents on phenyl rings, the breakage of the carbonate O-C bond is promoted or suppressed when the electron-donating or electron-withdrawing group is placed on the <i>meta</i>- or <i>ortho</i>-positions of the <i>gem</i>-dimethyl groups of phenyl rings, respectively. Moreover, the promotion and suppression of carbonate O-C bond scission are more significant if the substituents are located on the <i>ortho</i>-positions of the <i>gem</i>-dimethyl groups.https://www.mdpi.com/1420-3049/30/8/1839polycarbonatebond cleavageDFT/TDDFT
spellingShingle Xiao Huang
Yuuichi Orimoto
Yuriko Aoki
Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in Polycarbonate
Molecules
polycarbonate
bond cleavage
DFT/TDDFT
title Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in Polycarbonate
title_full Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in Polycarbonate
title_fullStr Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in Polycarbonate
title_full_unstemmed Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in Polycarbonate
title_short Mechanistic Study of Substituent Effect on Photoinduced O-C Bond Activation in Polycarbonate
title_sort mechanistic study of substituent effect on photoinduced o c bond activation in polycarbonate
topic polycarbonate
bond cleavage
DFT/TDDFT
url https://www.mdpi.com/1420-3049/30/8/1839
work_keys_str_mv AT xiaohuang mechanisticstudyofsubstituenteffectonphotoinducedocbondactivationinpolycarbonate
AT yuuichiorimoto mechanisticstudyofsubstituenteffectonphotoinducedocbondactivationinpolycarbonate
AT yurikoaoki mechanisticstudyofsubstituenteffectonphotoinducedocbondactivationinpolycarbonate