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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(01): 060-066
DOI: 10.1055/s-0041-1723767
Energy Materials in the Age of Globalization
Original Article

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

Shaofei Wu
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Hoa Phan
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Jing Li
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Haomin Xu
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Xing Li
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Dingguan Wang
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Tun Seng Herng
b   Department of Materials Science & Engineering, National University of Singapore, 119260, Singapore
,
Yi Han
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Andrew Wee 
c   Department of Physics, National University of Singapore, 2 Science Drive 3, 117542, Singapore
,
Jun Ding 
b   Department of Materials Science & Engineering, National University of Singapore, 119260, Singapore
,
Jiong Lu 
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
,
Jishan Wu 
a   Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore
d   Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, China
› Institutsangaben Funding Information This work was supported by National Research Foundation Singapore Competitive Research Programme (NRF-CRP16-2015-02), National Research Foundation Singapore Investigatorship (NRF-NRFI05-2019-0005), and Ministry of Education — Singapore Tier 2 grant (MOE2018-T2-2-094).
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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.

Key words

covalent organic frameworks - oxidative C–C coupling - liquid–liquid interfaces - conducting polymers - polypyrroles

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/s-0041-1723767.


Supporting Information



Publikationsverlauf

Eingereicht: 11. November 2020

Angenommen: 02. Januar 2021

Artikel online veröffentlicht:
16. Februar 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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