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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(01): 060-066
DOI: 10.1055/s-0041-1723767
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
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).
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 - polypyrrolesSupporting Information
Supporting Information for this article is available online at https://doi.org/10.1055/s-0041-1723767.
Publication History
Received: 11 November 2020
Accepted: 02 January 2021
Article published online:
16 February 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/)
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