Suspended Alicyclic Skeleton: Synthetic Approach to Zero-Birefringence Polycarbonate

Poly­(cyclohexene carbonate) (PCHC) is a recyclable, sustainable, alicyclic polycarbonate that can be synthesized from CO2. However, the optical properties of PCHC, including birefringence, are not well understood. Herein, we designed novel carbonate units via two approaches: “fusion” and “suspensio...

Full description

Saved in:
Bibliographic Details
Published inMacromolecules Vol. 57; no. 5; pp. 2413 - 2420
Main Authors Toda, Tatsuro, Nakata, Takuto, Fukuoka, Hiroshi, Yoneda, Hisanari
Format Journal Article
LanguageEnglish
Published American Chemical Society 12.03.2024
Online AccessGet full text

Cover

Abstract Poly­(cyclohexene carbonate) (PCHC) is a recyclable, sustainable, alicyclic polycarbonate that can be synthesized from CO2. However, the optical properties of PCHC, including birefringence, are not well understood. Herein, we designed novel carbonate units via two approaches: “fusion” and “suspension” of a norbornane skeleton to obtain PCHC-based zero-birefringence polycarbonates. Compared to PCHC, the in-plane retardation of the 100% uniaxially stretched norbornane-fused PCHC film was reduced, whereas the photoelastic coefficient unexpectedly increased. In contrast, the photoelastic birefringence of norbornane-suspended PCHC decreased. Furthermore, the copolymer synthesized via the copolymerization of cyclohexene carbonate with a tetracyclododecane-suspended monomer exhibited almost zero photoelastic birefringence. This result indicates that the photoelastic birefringence can be reduced by “suspending” the cyclic skeleton rather than “fusing” it. Computational studies suggested that the chair cyclohexane skeleton suppresses photoelastic birefringence. The results obtained in this study have the potential to guide the design of low-birefringence polycarbonates and other polymers.
AbstractList Poly­(cyclohexene carbonate) (PCHC) is a recyclable, sustainable, alicyclic polycarbonate that can be synthesized from CO2. However, the optical properties of PCHC, including birefringence, are not well understood. Herein, we designed novel carbonate units via two approaches: “fusion” and “suspension” of a norbornane skeleton to obtain PCHC-based zero-birefringence polycarbonates. Compared to PCHC, the in-plane retardation of the 100% uniaxially stretched norbornane-fused PCHC film was reduced, whereas the photoelastic coefficient unexpectedly increased. In contrast, the photoelastic birefringence of norbornane-suspended PCHC decreased. Furthermore, the copolymer synthesized via the copolymerization of cyclohexene carbonate with a tetracyclododecane-suspended monomer exhibited almost zero photoelastic birefringence. This result indicates that the photoelastic birefringence can be reduced by “suspending” the cyclic skeleton rather than “fusing” it. Computational studies suggested that the chair cyclohexane skeleton suppresses photoelastic birefringence. The results obtained in this study have the potential to guide the design of low-birefringence polycarbonates and other polymers.
Author Toda, Tatsuro
Yoneda, Hisanari
Nakata, Takuto
Fukuoka, Hiroshi
AuthorAffiliation Chemistry & Chemical Process Laboratory, Corporate Research & Development
Asahi Kasei Corporation
AuthorAffiliation_xml – name: Chemistry & Chemical Process Laboratory, Corporate Research & Development
– name: Asahi Kasei Corporation
Author_xml – sequence: 1
  givenname: Tatsuro
  surname: Toda
  fullname: Toda, Tatsuro
– sequence: 2
  givenname: Takuto
  surname: Nakata
  fullname: Nakata, Takuto
– sequence: 3
  givenname: Hiroshi
  surname: Fukuoka
  fullname: Fukuoka, Hiroshi
– sequence: 4
  givenname: Hisanari
  orcidid: 0009-0006-8961-5096
  surname: Yoneda
  fullname: Yoneda, Hisanari
  email: yoneda.hc@om.asahi-kasei.co.jp
BookMark eNp9kMFOwzAQRC1UJNrCH3DID6SsHTupuZUKClIlkFIuXCLX3tCU1I7s9JC_x1XLlcuutKNZzbwJGVlnkZB7CjMKjD4oHWYHpb07uHaWaWAZl1dkTAWDVMwzMSJjAMZTyWRxQyYh7AEoFTwbk015DB1agyZZtI0edBxJ-YMt9s4-JuVg-x328bboOu-U3iW9S77Qu_Sp8Vj7xn6j1Zh8uHbQym-dVT3ekutatQHvLntKPl-eN8vXdP2-elsu1qlinPapVFAXIGMDzlVRM0NrJrXiyCTdyjnmxhgKhcE5A4UCc0mRC5rn3AgsRJ1NCT__jdVDiHGqzjcH5YeKQnUiU0Uy1R-Z6kIm2uBsO6l7d_Q2hvzf8gs0Xm4V
Cites_doi 10.1002/pola.23044
10.1021/acsmacrolett.6b00591
10.1021/acs.macromol.0c01571
10.1021/ja206352x
10.1021/ma9012626
10.1021/acs.macromol.6b01492
10.1295/polymj.32.676
10.1016/j.envres.2019.108575
10.1021/jacs.9b06259
10.1002/pol.20210901
10.1039/C9GC00250B
10.1295/polymj.27.943
10.1039/b417973k
10.1021/ma300803b
10.1039/C9DT00595A
10.1364/AO.54.000779
10.1021/acs.inorgchem.0c01156
10.1021/acs.macromol.1c02101
10.1021/acs.oprd.8b00391
10.1021/ja992433b
10.1039/D0SC01609H
10.1021/ma0527000
10.1002/pat.3825
10.1039/C0CC02205E
10.1021/ma301110c
10.1038/pj.2015.7
10.1021/acssuschemeng.0c04335
10.1002/pol.1969.110070408
10.1021/acssuschemeng.9b00884
10.1039/B513107C
10.1038/nchem.2574
10.1002/chem.202101140
10.1021/ma010732r
10.1021/acs.macromol.9b02407
10.1038/s41557-020-0450-3
10.1021/acsapm.1c00149
10.1038/pj.2012.52
10.1122/1.550283
10.1038/pj.2013.50
10.1039/C9SC00385A
10.1021/acs.macromol.5b00548
10.1002/ange.202201785
10.1021/jacs.2c01436
10.1021/acs.orglett.9b01989
10.1038/s41428-019-0264-6
10.1016/j.polymer.2017.03.077
10.1038/pj.2011.141
10.1016/j.reactfunctpolym.2021.105145
10.1021/acs.inorgchem.7b02952
10.1021/ma102585a
10.1021/ma5009397
10.1039/c2sc00802e
10.1007/s00397-005-0454-3
10.1021/ma4000495
10.1021/acs.chemrev.0c01055
10.1021/jacs.6b11864
10.1002/pola.24150
10.1039/C7PY00236J
ContentType Journal Article
Copyright 2024 American Chemical Society
Copyright_xml – notice: 2024 American Chemical Society
DBID AAYXX
CITATION
DOI 10.1021/acs.macromol.3c02349
DatabaseName CrossRef
DatabaseTitle CrossRef
DatabaseTitleList
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1520-5835
EndPage 2420
ExternalDocumentID 10_1021_acs_macromol_3c02349
g90301313
GroupedDBID -~X
.K2
4.4
55A
5GY
5VS
7~N
AABXI
ABFRP
ABJNI
ABMVS
ABMYL
ABPPZ
ABQRX
ABUCX
ACBEA
ACGFO
ACGFS
ACJ
ACNCT
ACS
ADHLV
AEESW
AENEX
AFEFF
AHGAQ
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
BAANH
CS3
DU5
EBS
ED~
F5P
GGK
GNL
IH9
IHE
JG~
LG6
P2P
ROL
TN5
TWZ
UI2
VF5
VG9
W1F
WH7
YZZ
53G
AAHBH
AAYXX
AGXLV
CITATION
CUPRZ
ID FETCH-LOGICAL-a241t-9a0f70902144a7f2d1f29ca4e291b98e6ddd107de820ae5e691e451664d5e75f3
IEDL.DBID ACS
ISSN 0024-9297
IngestDate Fri Aug 23 01:24:38 EDT 2024
Wed Mar 13 05:13:56 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 5
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-a241t-9a0f70902144a7f2d1f29ca4e291b98e6ddd107de820ae5e691e451664d5e75f3
ORCID 0009-0006-8961-5096
PageCount 8
ParticipantIDs crossref_primary_10_1021_acs_macromol_3c02349
acs_journals_10_1021_acs_macromol_3c02349
PublicationCentury 2000
PublicationDate 2024-03-12
PublicationDateYYYYMMDD 2024-03-12
PublicationDate_xml – month: 03
  year: 2024
  text: 2024-03-12
  day: 12
PublicationDecade 2020
PublicationTitle Macromolecules
PublicationTitleAlternate Macromolecules
PublicationYear 2024
Publisher American Chemical Society
Publisher_xml – name: American Chemical Society
References ref9/cit9
ref45/cit45
ref3/cit3
ref27/cit27
ref63/cit63
ref56/cit56
ref16/cit16
ref52/cit52
ref23/cit23
ref8/cit8
ref31/cit31
ref2/cit2
ref34/cit34
ref37/cit37
ref20/cit20
ref48/cit48
ref60/cit60
ref17/cit17
ref10/cit10
ref35/cit35
ref53/cit53
ref19/cit19
ref21/cit21
ref42/cit42
ref46/cit46
ref49/cit49
ref13/cit13
Lamata M. P. (ref59/cit59) 2021
ref61/cit61
ref24/cit24
ref38/cit38
ref50/cit50
ref64/cit64
ref54/cit54
ref6/cit6
ref36/cit36
ref18/cit18
ref11/cit11
ref25/cit25
ref29/cit29
ref32/cit32
ref39/cit39
ref14/cit14
ref57/cit57
ref5/cit5
ref51/cit51
ref43/cit43
ref28/cit28
ref40/cit40
ref26/cit26
Belikova N. A. (ref55/cit55) 1965; 35
ref12/cit12
ref15/cit15
ref62/cit62
ref41/cit41
ref58/cit58
ref22/cit22
ref33/cit33
ref4/cit4
ref30/cit30
ref47/cit47
ref1/cit1
ref44/cit44
ref7/cit7
References_xml – ident: ref48/cit48
  doi: 10.1002/pola.23044
– ident: ref27/cit27
  doi: 10.1021/acsmacrolett.6b00591
– ident: ref29/cit29
  doi: 10.1021/acs.macromol.0c01571
– ident: ref15/cit15
  doi: 10.1021/ja206352x
– ident: ref13/cit13
  doi: 10.1021/ma9012626
– ident: ref31/cit31
  doi: 10.1021/acs.macromol.6b01492
– ident: ref62/cit62
  doi: 10.1295/polymj.32.676
– ident: ref4/cit4
– ident: ref2/cit2
  doi: 10.1016/j.envres.2019.108575
– ident: ref33/cit33
  doi: 10.1021/jacs.9b06259
– ident: ref40/cit40
  doi: 10.1002/pol.20210901
– ident: ref56/cit56
  doi: 10.1039/C9GC00250B
– ident: ref44/cit44
– ident: ref52/cit52
  doi: 10.1295/polymj.27.943
– ident: ref11/cit11
  doi: 10.1039/b417973k
– ident: ref18/cit18
  doi: 10.1021/ma300803b
– ident: ref20/cit20
  doi: 10.1039/C9DT00595A
– ident: ref45/cit45
  doi: 10.1364/AO.54.000779
– ident: ref24/cit24
  doi: 10.1021/acs.inorgchem.0c01156
– ident: ref54/cit54
  doi: 10.1021/acs.macromol.1c02101
– ident: ref1/cit1
  doi: 10.1021/acs.oprd.8b00391
– ident: ref9/cit9
  doi: 10.1021/ja992433b
– ident: ref23/cit23
  doi: 10.1039/D0SC01609H
– ident: ref47/cit47
  doi: 10.1021/ma0527000
– ident: ref64/cit64
– ident: ref49/cit49
  doi: 10.1002/pat.3825
– ident: ref14/cit14
  doi: 10.1039/C0CC02205E
– ident: ref41/cit41
  doi: 10.1021/ma301110c
– ident: ref51/cit51
  doi: 10.1038/pj.2015.7
– ident: ref57/cit57
  doi: 10.1021/acssuschemeng.0c04335
– ident: ref8/cit8
  doi: 10.1002/pol.1969.110070408
– ident: ref35/cit35
  doi: 10.1021/acssuschemeng.9b00884
– ident: ref12/cit12
  doi: 10.1039/B513107C
– ident: ref26/cit26
  doi: 10.1038/nchem.2574
– ident: ref25/cit25
  doi: 10.1002/chem.202101140
– ident: ref10/cit10
  doi: 10.1021/ma010732r
– ident: ref42/cit42
  doi: 10.1021/acs.macromol.9b02407
– ident: ref22/cit22
  doi: 10.1038/s41557-020-0450-3
– ident: ref63/cit63
  doi: 10.1021/acsapm.1c00149
– start-page: 67
  volume-title: Iridium Catalysts for Organic Reactions
  year: 2021
  ident: ref59/cit59
  contributor:
    fullname: Lamata M. P.
– ident: ref61/cit61
  doi: 10.1038/pj.2012.52
– ident: ref3/cit3
  doi: 10.1122/1.550283
– ident: ref37/cit37
  doi: 10.1038/pj.2013.50
– ident: ref21/cit21
  doi: 10.1039/C9SC00385A
– ident: ref39/cit39
  doi: 10.1021/acs.macromol.5b00548
– ident: ref43/cit43
  doi: 10.1002/ange.202201785
– ident: ref30/cit30
  doi: 10.1021/jacs.2c01436
– ident: ref60/cit60
  doi: 10.1021/acs.orglett.9b01989
– ident: ref36/cit36
  doi: 10.1038/s41428-019-0264-6
– ident: ref5/cit5
  doi: 10.1016/j.polymer.2017.03.077
– ident: ref46/cit46
  doi: 10.1038/pj.2011.141
– ident: ref6/cit6
  doi: 10.1016/j.reactfunctpolym.2021.105145
– ident: ref19/cit19
  doi: 10.1021/acs.inorgchem.7b02952
– ident: ref16/cit16
  doi: 10.1021/ma102585a
– ident: ref38/cit38
  doi: 10.1021/ma5009397
– ident: ref17/cit17
  doi: 10.1039/c2sc00802e
– ident: ref53/cit53
  doi: 10.1007/s00397-005-0454-3
– ident: ref34/cit34
  doi: 10.1021/ma4000495
– ident: ref58/cit58
  doi: 10.1021/acs.chemrev.0c01055
– ident: ref28/cit28
  doi: 10.1021/jacs.6b11864
– ident: ref7/cit7
– ident: ref50/cit50
  doi: 10.1002/pola.24150
– ident: ref32/cit32
  doi: 10.1039/C7PY00236J
– volume: 35
  start-page: 1745
  year: 1965
  ident: ref55/cit55
  publication-title: J. Gen. Chem. USSR
  contributor:
    fullname: Belikova N. A.
SSID ssj0011543
Score 2.4888394
Snippet Poly­(cyclohexene carbonate) (PCHC) is a recyclable, sustainable, alicyclic polycarbonate that can be synthesized from CO2. However, the optical properties of...
SourceID crossref
acs
SourceType Aggregation Database
Publisher
StartPage 2413
Title Suspended Alicyclic Skeleton: Synthetic Approach to Zero-Birefringence Polycarbonate
URI http://dx.doi.org/10.1021/acs.macromol.3c02349
Volume 57
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV07T8MwELagDLDwRpSXPLAwuDSOEydspQJVSDyktlLFEjn2eWlpUJsO5ddzThOoQCBYMliJZZ3P-b7zvQg5V4EIoyZIhvaPZkJDwGJtQqZ4KmxoA-1FLnf4_iHs9MXdIBh8GopfPfjcu1R62nhRRXDaqOFrxBgRr5I1LvF8OCrU7n54DZAOLDzKXDCEfVmlyv0wiwMkPV0CpCVkud0ij1V-ziKgZNiY5WlDv30v1_jHRW-TzZJk0tZCK3bICox3yXq76u22R3rd2bRofmtoy9UF1vig3SFCEFLBK9qdj5EX4se0VZYcp3lGn2GSsWv8RdriLhC1hT5lo7lWk9RdwcM-6d_e9NodVvZXwJ0QXs5i1bTSxWWiUaWk5cazPNZKAI-9NI4gNMagdWgAWYKCAMLYA9fXNxQmABlY_4DUxtkYDgnlSvlgo6bmUgkhIZIgUA2Mb01spPTr5AJFkpTnY5oUrm_uJW6wklNSyqlOWLUhyeui5Mav7x_9Y-5jssGddriAPH5CavlkBqfIKvL0rFCld6trysI
link.rule.ids 315,783,787,2772,27088,27936,27937,57066,57116
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LT9wwEB4BPcAFKG1VHgUfuPTgZePYccJtWYGWpyrtUiEukWOPL9BdtMke4NczziYUIYHEJQcrHo3sSb7PnhfAvlEySbuoOZ1_LJcWFc-sS7gRhfSJVzZKQ-7w5VUyuJZnN-pmAVSbC0NKlCSprJ34_6sLRAdh7J-pY9TuO7ElqJHZInxRmjAzMKL-8MV5QKxg7lgWkhP66zZj7h0pAZds-QqXXgHMyRr8fVGtjiu568yqomOf3lRt_LTu67DaUE7Wm9vIV1jA8QYs99tOb99gNJyVdStcx3qhSrClBxveESARMTxkw8cxsUSazHpNAXJWTdgtTif8iH6Yvr4ZJNthfyb3j9ZMi3Ahj9_h-uR41B_wptsC7YuMKp6ZrtchSpOOWEZ74SIvMmskiiwqshQT5xydFR0SZzCoMMkiDF1-E-kUauXjH7A0nozxJzBhTIw-7VqhjZQaU42SjMLF3mVO63gTftOS5M3XUua1I1xEeRhs1ylv1mkTeLsv-cO8AMeH7299QvYeLA9Glxf5xenV-TasiGAwIVRP7MBSNZ3hL-IbVbFbW9czoTXTJw
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LT8MwDI5gSMCFN2I8c-DCIWNN06blNgYTb03aJk1cqjRxLoMNrd0Bfj1O16EJCSS45BClluU49efYsQk5VYEIozpIhv6PZkJDwGJtQqZ4KmxoA-1F7u3w41N40xN3_aA_1-oLmciQUlYE8d2pfjO2rDDgnbv5V1Xkqb3UfI3mRsSLZCmQXhGhbTQ7XwEERAbT4DIXDBGAnL2a-4GKs006m7NNc0amtU6ev9grcksGtUme1vTHt8qN_-J_g6yV0JM2prqySRZguEVWmrOOb9uk25lkRUtcQxuuWrDGgXYGaJgQIF7QzvsQ0SJ-TBtlIXKaj-gzjEfsEn-ctrghRB2i7dHLu1bj1F3Mww7pta67zRtWdl3A_RFezmJVt9Jla6KrpaTlxrM81koAj700jiA0xqDPaACxg4IAwtgD1-03FCYAGVh_l1SGoyHsEcqV8sFGdc2lEkJCJEGgchjfmthI6VfJGYokKU9NlhQBce4lbnImp6SUU5Ww2d4kb9NCHL-u3_8D7ROy3L5qJQ-3T_cHZJU7nXEZe_yQVPLxBI4QduTpcaFgn22m1aE
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Suspended+Alicyclic+Skeleton%3A+Synthetic+Approach+to+Zero-Birefringence+Polycarbonate&rft.jtitle=Macromolecules&rft.au=Toda%2C+Tatsuro&rft.au=Nakata%2C+Takuto&rft.au=Fukuoka%2C+Hiroshi&rft.au=Yoneda%2C+Hisanari&rft.date=2024-03-12&rft.issn=0024-9297&rft.eissn=1520-5835&rft.volume=57&rft.issue=5&rft.spage=2413&rft.epage=2420&rft_id=info:doi/10.1021%2Facs.macromol.3c02349&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_acs_macromol_3c02349
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0024-9297&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0024-9297&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0024-9297&client=summon