Synthesis of a Large, Shape-Flexible, Solvatomorphic Porous Organic Cage

Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported, large multicomponent organic cages with 20 components or more are still rare. Here, we present an [8 + 12] porous organic imine cage, CC20, wh...

Full description

Saved in:
Bibliographic Details
Published inCrystal growth & design Vol. 19; no. 7; pp. 3647 - 3651
Main Authors Teng, Baiyang, Little, Marc A, Hasell, Tom, Chong, Samantha Y, Jelfs, Kim E, Clowes, Rob, Briggs, Michael E, Cooper, Andrew I
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 03.07.2019
Online AccessGet full text

Cover

Loading…
Abstract Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported, large multicomponent organic cages with 20 components or more are still rare. Here, we present an [8 + 12] porous organic imine cage, CC20, which has an apparent surface area up to 1752 m2 g–1, depending on the crystallization and activation conditions. The cage is solvatomorphic and displays distinct geometrical cage structures, caused by crystal-packing effects, in its crystal structures. This indicates that larger cages can display a certain range of shape flexibility in the solid state, while remaining shape persistent and porous.
AbstractList Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported, large multicomponent organic cages with 20 components or more are still rare. Here, we present an [8 + 12] porous organic imine cage, CC20, which has an apparent surface area up to 1752 m2 g–1, depending on the crystallization and activation conditions. The cage is solvatomorphic and displays distinct geometrical cage structures, caused by crystal-packing effects, in its crystal structures. This indicates that larger cages can display a certain range of shape flexibility in the solid state, while remaining shape persistent and porous.
Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported, large multicomponent organic cages with 20 components or more are still rare. Here, we present an [8 + 12] porous organic imine cage, , which has an apparent surface area up to 1752 m g , depending on the crystallization and activation conditions. The cage is solvatomorphic and displays distinct geometrical cage structures, caused by crystal-packing effects, in its crystal structures. This indicates that larger cages can display a certain range of shape flexibility in the solid state, while remaining shape persistent and porous.
Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported, large multicomponent organic cages with 20 components or more are still rare. Here, we present an [8 + 12] porous organic imine cage, CC20, which has an apparent surface area up to 1752 m2 g-1, depending on the crystallization and activation conditions. The cage is solvatomorphic and displays distinct geometrical cage structures, caused by crystal-packing effects, in its crystal structures. This indicates that larger cages can display a certain range of shape flexibility in the solid state, while remaining shape persistent and porous.Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported, large multicomponent organic cages with 20 components or more are still rare. Here, we present an [8 + 12] porous organic imine cage, CC20, which has an apparent surface area up to 1752 m2 g-1, depending on the crystallization and activation conditions. The cage is solvatomorphic and displays distinct geometrical cage structures, caused by crystal-packing effects, in its crystal structures. This indicates that larger cages can display a certain range of shape flexibility in the solid state, while remaining shape persistent and porous.
Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported, large multicomponent organic cages with 20 components or more are still rare. Here, we present an [8 + 12] porous organic imine cage, CC20 , which has an apparent surface area up to 1752 m 2 g –1 , depending on the crystallization and activation conditions. The cage is solvatomorphic and displays distinct geometrical cage structures, caused by crystal-packing effects, in its crystal structures. This indicates that larger cages can display a certain range of shape flexibility in the solid state, while remaining shape persistent and porous. By increasing the bend angle between amine groups in diaminocyclohexane precursors, we have successfully directed the formation of an [8 + 12] porous organic cage. The cuboctahedral-shaped cage is flexible in the solid state, and it can be processed into two different porous crystalline solids, which have contrasting stabilities and sorption properties.
Author Hasell, Tom
Chong, Samantha Y
Teng, Baiyang
Jelfs, Kim E
Cooper, Andrew I
Briggs, Michael E
Little, Marc A
Clowes, Rob
AuthorAffiliation Department of Chemistry
Department of Chemistry and Materials Innovation Factory
AuthorAffiliation_xml – name: Department of Chemistry and Materials Innovation Factory
– name: Department of Chemistry
Author_xml – sequence: 1
  givenname: Baiyang
  surname: Teng
  fullname: Teng, Baiyang
  organization: Department of Chemistry and Materials Innovation Factory
– sequence: 2
  givenname: Marc A
  surname: Little
  fullname: Little, Marc A
  email: malittle@liverpool.ac.uk
  organization: Department of Chemistry and Materials Innovation Factory
– sequence: 3
  givenname: Tom
  surname: Hasell
  fullname: Hasell, Tom
  organization: Department of Chemistry and Materials Innovation Factory
– sequence: 4
  givenname: Samantha Y
  orcidid: 0000-0002-3095-875X
  surname: Chong
  fullname: Chong, Samantha Y
  organization: Department of Chemistry and Materials Innovation Factory
– sequence: 5
  givenname: Kim E
  orcidid: 0000-0001-7683-7630
  surname: Jelfs
  fullname: Jelfs, Kim E
  organization: Department of Chemistry
– sequence: 6
  givenname: Rob
  surname: Clowes
  fullname: Clowes, Rob
  organization: Department of Chemistry and Materials Innovation Factory
– sequence: 7
  givenname: Michael E
  orcidid: 0000-0003-1474-1267
  surname: Briggs
  fullname: Briggs, Michael E
  organization: Department of Chemistry and Materials Innovation Factory
– sequence: 8
  givenname: Andrew I
  orcidid: 0000-0003-0201-1021
  surname: Cooper
  fullname: Cooper, Andrew I
  email: aicooper@liverpool.ac.uk
  organization: Department of Chemistry and Materials Innovation Factory
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31303868$$D View this record in MEDLINE/PubMed
BookMark eNp9UU1LxDAQDaL4ffYmPQraNR9Nm14EWfyCBQW9h0madCPdZk26ov_eLLuKCnqaGea9N8l7e2iz971B6IjgEcGUnIOOI902I6EwqUqygXYJpyKvOOabn30h2A7ai_EZY1yVjG2jHUYYZqIUu-j28b0fpia6mHmbQTaB0Jqz7HEKc5Nfd-bNqW45--4VBj_zYT51OnvwwS9idh9a6NM4htYcoC0LXTSH67qPnq6vnsa3-eT-5m58OcmhqPmQCxBFbXRjlWINMKqs1bQmolKNtmWjhKWCFURoCpRTXitqORQUGDNEa8X20cVKdr5QM9No0w8BOjkPbgbhXXpw8uemd1PZ-ldZlqQQVZ0ETtYCwb8sTBzkzEVtug56k_4kKeUi-VYUVYIef7_1deTTvQQ4XwF08DEGY78gBMtlPjLlI1M-cp1PYvBfDO0GGJxfPtZ1__BOV7zl4tkvQp88_hP9AdhupeA
CitedBy_id crossref_primary_10_1021_acsami_0c11200
crossref_primary_10_1002_chem_202003864
crossref_primary_10_1021_acs_jced_0c00776
crossref_primary_10_1360_SSC_2023_0190
crossref_primary_10_1016_j_molliq_2023_121536
crossref_primary_10_1039_D1SC06372C
crossref_primary_10_1039_D0CC00932F
crossref_primary_10_1039_D4SC00889H
crossref_primary_10_1002_chem_202302116
crossref_primary_10_1021_jacs_0c07367
crossref_primary_10_1016_j_molliq_2024_124731
crossref_primary_10_1021_acsami_9b19480
crossref_primary_10_1039_D1QO00478F
crossref_primary_10_1021_jacs_0c04885
crossref_primary_10_1002_anie_202102982
crossref_primary_10_1021_acs_cgd_0c00407
crossref_primary_10_1039_D3CC05091B
crossref_primary_10_1002_adfm_201909842
crossref_primary_10_1002_ejic_202100986
crossref_primary_10_1002_ange_202102982
crossref_primary_10_1002_cplu_202000445
crossref_primary_10_1038_s41467_023_40255_4
crossref_primary_10_1039_D4TA07124G
crossref_primary_10_1021_jacs_3c06175
Cites_doi 10.1039/C6CC01034B
10.1021/acs.chemmater.6b02903
10.1002/anie.201710190
10.1002/adma.201202786
10.1002/anie.201308924
10.1038/natrevmats.2016.53
10.1021/jacs.5b11797
10.1039/C6OB01429A
10.1039/C8FD00031J
10.1039/C7CC09918E
10.1021/ja800803c
10.1002/anie.201105104
10.1021/ja210418t
10.1002/anie.201208156
10.1039/C4CC08883B
10.1246/cl.150021
10.1039/C5CS00878F
10.1039/c3cc39098e
10.1039/C6SC05196K
10.1021/acs.jpcb.6b03059
10.1021/jacs.5b02716
10.1038/nmat4035
10.1038/nature16072
10.1039/C4CC01794C
10.1039/c2cs35157a
10.1021/ja0644733
10.1021/acs.jpcc.7b03848
10.1039/C3CS60358J
10.1002/anie.201502983
10.1021/jacs.5b13307
10.1126/science.1188605
10.1021/ja412606t
10.1021/cr300014x
10.1038/nmat2545
10.1039/C7SC03148C
ContentType Journal Article
Copyright Copyright © 2019 American Chemical Society 2019 American Chemical Society
Copyright_xml – notice: Copyright © 2019 American Chemical Society 2019 American Chemical Society
DBID AAYXX
CITATION
NPM
7X8
5PM
DOI 10.1021/acs.cgd.8b01761
DatabaseName CrossRef
PubMed
MEDLINE - Academic
PubMed Central (Full Participant titles)
DatabaseTitle CrossRef
PubMed
MEDLINE - Academic
DatabaseTitleList
PubMed
MEDLINE - Academic

Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Engineering
Chemistry
EISSN 1528-7505
EndPage 3651
ExternalDocumentID PMC6614879
31303868
10_1021_acs_cgd_8b01761
c023353595
Genre Journal Article
GroupedDBID 55A
5GY
7~N
AABXI
ABMVS
ABPTK
ABUCX
ACGFS
ACS
AEESW
AENEX
AFEFF
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
CS3
DU5
EBS
ED
ED~
EJD
F5P
GNL
IH9
JG
JG~
P2P
RNS
ROL
TN5
UI2
VF5
VG9
W1F
X
-~X
4.4
5VS
6J9
AAYXX
ABBLG
ABJNI
ABLBI
ABQRX
ADHLV
AHGAQ
BAANH
CITATION
CUPRZ
GGK
NPM
7X8
5PM
ID FETCH-LOGICAL-a495t-8a849ecdfbb3da32bffc29187bdcf6db8f283418c2a25259b2f5a42a33e1ccb3
IEDL.DBID ACS
ISSN 1528-7483
IngestDate Thu Aug 21 18:14:19 EDT 2025
Fri Jul 11 08:46:49 EDT 2025
Thu Jan 02 23:01:39 EST 2025
Tue Jul 01 01:00:03 EDT 2025
Thu Apr 24 23:06:08 EDT 2025
Thu Aug 27 13:41:54 EDT 2020
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 7
Language English
License http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html
This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-a495t-8a849ecdfbb3da32bffc29187bdcf6db8f283418c2a25259b2f5a42a33e1ccb3
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ORCID 0000-0002-3095-875X
0000-0003-0201-1021
0000-0003-1474-1267
0000-0001-7683-7630
OpenAccessLink https://pubmed.ncbi.nlm.nih.gov/PMC6614879
PMID 31303868
PQID 2258152447
PQPubID 23479
PageCount 5
ParticipantIDs pubmedcentral_primary_oai_pubmedcentral_nih_gov_6614879
proquest_miscellaneous_2258152447
pubmed_primary_31303868
crossref_primary_10_1021_acs_cgd_8b01761
crossref_citationtrail_10_1021_acs_cgd_8b01761
acs_journals_10_1021_acs_cgd_8b01761
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
7~N
VG9
W1F
ACS
AEESW
AFEFF
ABMVS
ABUCX
IH9
AQSVZ
ED~
UI2
CITATION
AAYXX
PublicationCentury 2000
PublicationDate 2019-Jul-03
PublicationDateYYYYMMDD 2019-07-03
PublicationDate_xml – month: 07
  year: 2019
  text: 2019-Jul-03
  day: 03
PublicationDecade 2010
PublicationPlace United States
PublicationPlace_xml – name: United States
PublicationTitle Crystal growth & design
PublicationTitleAlternate Cryst. Growth Des
PublicationYear 2019
Publisher American Chemical Society
Publisher_xml – name: American Chemical Society
References ref9/cit9
ref6/cit6
ref36/cit36
ref27/cit27
ref18/cit18
ref11/cit11
ref25/cit25
ref16/cit16
ref29/cit29
ref23/cit23
ref14/cit14
ref8/cit8
ref5/cit5
ref31/cit31
ref2/cit2
ref34/cit34
ref37/cit37
ref28/cit28
ref20/cit20
ref17/cit17
ref10/cit10
ref26/cit26
ref35/cit35
ref19/cit19
ref21/cit21
ref12/cit12
ref15/cit15
ref22/cit22
Chong S. Y. (ref3/cit3) 2017
ref13/cit13
ref33/cit33
ref4/cit4
ref30/cit30
ref1/cit1
ref24/cit24
ref38/cit38
ref7/cit7
References_xml – ident: ref18/cit18
  doi: 10.1039/C6CC01034B
– ident: ref36/cit36
  doi: 10.1021/acs.chemmater.6b02903
– ident: ref4/cit4
  doi: 10.1002/anie.201710190
– ident: ref12/cit12
  doi: 10.1002/adma.201202786
– ident: ref27/cit27
  doi: 10.1002/anie.201308924
– ident: ref6/cit6
  doi: 10.1038/natrevmats.2016.53
– ident: ref10/cit10
  doi: 10.1021/jacs.5b11797
– ident: ref35/cit35
  doi: 10.1039/C6OB01429A
– ident: ref38/cit38
  doi: 10.1039/C8FD00031J
– ident: ref14/cit14
  doi: 10.1039/C7CC09918E
– ident: ref25/cit25
  doi: 10.1021/ja800803c
– ident: ref31/cit31
  doi: 10.1002/anie.201105104
– ident: ref11/cit11
  doi: 10.1021/ja210418t
– ident: ref37/cit37
  doi: 10.1002/anie.201208156
– volume-title: Porous Organic Cages
  year: 2017
  ident: ref3/cit3
– ident: ref34/cit34
  doi: 10.1039/C4CC08883B
– ident: ref5/cit5
  doi: 10.1246/cl.150021
– ident: ref20/cit20
  doi: 10.1039/C5CS00878F
– ident: ref28/cit28
  doi: 10.1039/c3cc39098e
– ident: ref23/cit23
  doi: 10.1039/C6SC05196K
– ident: ref13/cit13
  doi: 10.1021/acs.jpcb.6b03059
– ident: ref24/cit24
  doi: 10.1021/jacs.5b02716
– ident: ref8/cit8
  doi: 10.1038/nmat4035
– ident: ref22/cit22
  doi: 10.1038/nature16072
– ident: ref29/cit29
  doi: 10.1039/C4CC01794C
– ident: ref21/cit21
  doi: 10.1039/c2cs35157a
– ident: ref7/cit7
  doi: 10.1002/anie.201308924
– ident: ref26/cit26
  doi: 10.1021/ja0644733
– ident: ref9/cit9
  doi: 10.1021/acs.jpcc.7b03848
– ident: ref2/cit2
  doi: 10.1039/C3CS60358J
– ident: ref30/cit30
  doi: 10.1002/anie.201502983
– ident: ref15/cit15
  doi: 10.1021/jacs.5b13307
– ident: ref33/cit33
  doi: 10.1126/science.1188605
– ident: ref17/cit17
  doi: 10.1021/ja412606t
– ident: ref19/cit19
  doi: 10.1021/cr300014x
– ident: ref1/cit1
  doi: 10.1038/nmat2545
– ident: ref16/cit16
  doi: 10.1039/C7SC03148C
SSID ssj0007633
Score 2.4013932
Snippet Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported,...
Porous organic cages have emerged over the last 10 years as a subclass of functional microporous materials. However, among all of the organic cages reported,...
SourceID pubmedcentral
proquest
pubmed
crossref
acs
SourceType Open Access Repository
Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 3647
Title Synthesis of a Large, Shape-Flexible, Solvatomorphic Porous Organic Cage
URI http://dx.doi.org/10.1021/acs.cgd.8b01761
https://www.ncbi.nlm.nih.gov/pubmed/31303868
https://www.proquest.com/docview/2258152447
https://pubmed.ncbi.nlm.nih.gov/PMC6614879
Volume 19
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LS8QwEA6iB_Xg-7G-iODBg11tkrbJURaXRVSEVfBWkjRxF9dW7K6gv95J262ui-ixzQMyM8l8w0y-IHR0RjU0MOkJGRAIUEToySCwnpYhkUxQK63L6F7fhJ17dvkQPHyRRf_M4BP_VGoQ_mPS5AqMxwU6cySELexQUKtbH7qwTYpa-oAU9Ji0ZvGZmsC5IZ1PuqEpbPmzRPKbz2kvl9VaeUFV6EpNnpqjoWrqj2kix7-Xs4KWKuSJz0tTWUUzJl1D863xg29raPEbN-E66nTfUwCHeT_HmcUSX7mS8RPc7ckX47UdjaYauO9s8AZx-3MG-uprfJu9ZqMclzc8NW7BabWB7toXd62OVz274IFygqHHJWfC6MQqRRNJibJWE-HzSCXahoniFiAJ87kmkgQQPSliA8mIpNT4Wiu6iWbTLDXbCHPHPAAhHTVCMaO48pMIdE_JWShFyJIGOgJxxNWuyeMiIU782P0EGcWVjBqoOdZVrCvmcveAxuD3Acf1gJeStOP3rodj5ccgbpctkakBScVw0HEwJ8aiBtoqjaGejDrPz0PeQNGEmdQdHGn3ZEva7xXk3Q4P8Ujs_G_pu2gBEJoo6oPpHpodvo7MPqCgoToo7P8TAGkDhw
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3Pb9MwFH6axmHswI8xoPyakXbgsHSN7ST2saqoyugmUIu0W2Q7Nq0oSdW0SPDX85ymod00iR3j2Jb9_Nn-nvz8GeC0wwz-4CqQKqLooMg4UFHkAqNiqrhkTjl_ont5FQ--8Yvr6HoPOpu7MNiIEmsqq0P8f-oC4blPM9-zttCIIe_vPEAqQj2mu71Rs_bibKlC6iNaqWSyRsznVgV-NzLl7m50i2LejJTc2nr6j-Fr0-gq4uRHe7XUbfPnhp7jfXr1BB7VPJR018B5Cns2P4KD3ub5tyM43FIqfAaD0e8cqWI5LUnhiCJDH0B-RkYTNbdB34tq6pn_Lma_0Iv_WeDoTQ35UiyKVUnW9z0N6eHadQzj_sdxbxDUjzAEOFTRMhBKcGlN5rRmmWJUO2eoDEWiM-PiTAuHBIWHwlBFI_SlNHWR4lQxZkNjNHsO-3mR25dAhNchQAePWam51UKHWYJIYLQTKxnzrAWnaI60nkNlWh2P0zD1iWijtLZRC9qbIUtNrWPun9OY3V3gQ1NgvpbwuDvr-w0GUjS3PztRuUVLpbjsCUQV50kLXqwx0VTGPA8QsWhBsoOWJoOX8N79k08nlZS3Z0cika_-r-sncDAYXw7T4aerz6_hIXI3WUUOszewv1ys7FvkR0v9rpoSfwFExwvo
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3db9MwED-hIQF74GPAKJ9G2gMPpCy2k9iPU6EqMKZJ3aS9RbZjb9VKUi3tpPHXc5em0bppEjzGsS37_Dv7Tnf-GWBnVzj8IU2kTcLRQdFpZJIkRM6k3EgtggkU0f11kI6O5Y-T5KS9FEZ3YXAQNfZUN0F80upZEVqGgfgLlbvToq8s4oh8nvsUtCNc7w3G3f6LGtOk1Se8YcoUHaHPrQ7oRHL1-ol0y8y8mS157fgZPoHjbuBN1sl5fzG3fffnBqfj_87sKTxu7VG2twTQM7jnyy14OFg9A7cFm9cYC5_DaHxVoslYT2pWBWbYPiWSf2bjMzPz0ZDINe2UvqvpJXrzvytcxYljh9VFtajZ8t6nYwPcw17A0fDb0WAUtY8xRLhkyTxSRkntXRGsFYUR3IbguI5VZgsX0sKqgIaKjJXjhifoU1keEiO5EcLHzlnxEjbKqvSvgCniI0BHT3htpbfKxkWGiBB8NzU6lUUPdlAceatLdd6EyXmcUyHKKG9l1IP-atly1_KZ07Ma07sbfOoazJZUHndX_bjCQY7iphiKKT1KKsftTyGypMx6sL3ERdeZIHtApaoH2RpiugpE5b3-p5ycNZTeZCWpTL_-t6l_gAeHX4f5_veDn2_gEZpwukkgFm9hY36x8O_QTJrb941W_AXhBA5r
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=Synthesis+of+a+Large%2C+Shape-Flexible%2C+Solvatomorphic+Porous+Organic+Cage&rft.jtitle=Crystal+growth+%26+design&rft.au=Teng%2C+Baiyang&rft.au=Little%2C+Marc+A&rft.au=Hasell%2C+Tom&rft.au=Chong%2C+Samantha+Y&rft.date=2019-07-03&rft.issn=1528-7483&rft.volume=19&rft.issue=7&rft.spage=3647&rft_id=info:doi/10.1021%2Facs.cgd.8b01761&rft.externalDBID=NO_FULL_TEXT
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1528-7483&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1528-7483&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1528-7483&client=summon