Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface

Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface

Abstract The construction of conjugated covalent organic frameworks (COFs) with strong C–C bond linkage remains a big challenge. Herein, we report a new strategy by using an oxidative C–C coupling reaction between electron-rich pyrrole rings at a liquid–liquid interface. Two threefold symmetric mono...

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Main Authors: Shaofei Wu, Hoa Phan, Jing Li, Haomin Xu, Xing Li, Dingguan Wang, Tun Seng Herng, Yi Han, Andrew Wee, Jun Ding, Jiong Lu, Jishan Wu
Format: Article
Language:English
Published: Georg Thieme Verlag 2021-01-01
Series:Organic Materials
Subjects:
covalent organic frameworks
oxidative c–c coupling
liquid–liquid interfaces
conducting polymers
polypyrroles
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1723767
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spelling doaj-c01863e334484e0cb3be2f42afa6b8542021-02-17T00:30:36ZengGeorg Thieme VerlagOrganic Materials2625-18252021-01-01030106006610.1055/s-0041-1723767Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid InterfaceShaofei Wu0Hoa Phan1Jing Li2Haomin Xu3Xing Li4Dingguan Wang5Tun Seng Herng6Yi Han7Andrew Wee8Jun Ding9Jiong Lu10Jishan Wu11Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Materials Science & Engineering, National University of Singapore, 119260, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Physics, National University of Singapore, 2 Science Drive 3, 117542, SingaporeDepartment of Materials Science & Engineering, National University of Singapore, 119260, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, SingaporeAbstract The construction of conjugated covalent organic frameworks (COFs) with strong C–C bond linkage remains a big challenge. Herein, we report a new strategy by using an oxidative C–C coupling reaction between electron-rich pyrrole rings at a liquid–liquid interface. Two threefold symmetric monomers containing three terminal pyrrole units were tested, and both gave two-dimensional conjugated COF films with good crystallinity. The bipyrrole units in the as-formed COFs are partially doped, which can be reduced to the neutral form by hydrazine and redoped by I2 vapor. The I2-doped films showed high conductivity (1.35 S/m). Meanwhile, the unpaired electrons exhibited moderate interlayer antiferromagnetic coupling.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1723767covalent organic frameworksoxidative c–c couplingliquid–liquid interfacesconducting polymerspolypyrroles
collection DOAJ
language English
format Article
sources DOAJ
author Shaofei Wu
Hoa Phan
Jing Li
Haomin Xu
Xing Li
Dingguan Wang
Tun Seng Herng
Yi Han
Andrew Wee
Jun Ding
Jiong Lu
Jishan Wu
spellingShingle Shaofei Wu
Hoa Phan
Jing Li
Haomin Xu
Xing Li
Dingguan Wang
Tun Seng Herng
Yi Han
Andrew Wee
Jun Ding
Jiong Lu
Jishan Wu
Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface
Organic Materials
covalent organic frameworks
oxidative c–c coupling
liquid–liquid interfaces
conducting polymers
polypyrroles
author_facet Shaofei Wu
Hoa Phan
Jing Li
Haomin Xu
Xing Li
Dingguan Wang
Tun Seng Herng
Yi Han
Andrew Wee
Jun Ding
Jiong Lu
Jishan Wu
author_sort Shaofei Wu
title Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface
title_short Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface
title_full Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface
title_fullStr Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface
title_full_unstemmed Two-Dimensional Conjugated Covalent Organic Framework Films via Oxidative C–C Coupling Reactions at a Liquid–Liquid Interface
title_sort two-dimensional conjugated covalent organic framework films via oxidative c–c coupling reactions at a liquid–liquid interface
publisher Georg Thieme Verlag
series Organic Materials
issn 2625-1825
publishDate 2021-01-01
description Abstract The construction of conjugated covalent organic frameworks (COFs) with strong C–C bond linkage remains a big challenge. Herein, we report a new strategy by using an oxidative C–C coupling reaction between electron-rich pyrrole rings at a liquid–liquid interface. Two threefold symmetric monomers containing three terminal pyrrole units were tested, and both gave two-dimensional conjugated COF films with good crystallinity. The bipyrrole units in the as-formed COFs are partially doped, which can be reduced to the neutral form by hydrazine and redoped by I2 vapor. The I2-doped films showed high conductivity (1.35 S/m). Meanwhile, the unpaired electrons exhibited moderate interlayer antiferromagnetic coupling.
topic covalent organic frameworks
oxidative c–c coupling
liquid–liquid interfaces
conducting polymers
polypyrroles
url http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1723767
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AT jingli twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
AT haominxu twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
AT xingli twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
AT dingguanwang twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
AT tunsengherng twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
AT yihan twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
AT andrewwee twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
AT junding twodimensionalconjugatedcovalentorganicframeworkfilmsviaoxidativecccouplingreactionsataliquidliquidinterface
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