Synthesis of Vinylene-Linked Covalent Organic Frameworks from Acetonitrile: Combining Cyclotrimerization and Aldol Condensation in One Pot

Journal of the American Chemical Society
Amitava AcharjyaArne Thomas

Abstract

Combining two or more consecutive reactions in one pot is a common approach for process development, as such a method involves cheap starting materials and allows in situ generation of a reactive intermediate, to undergo further reaction, without isolation. Herein, we report the synthesis of a vinylene-linked (-CH═CH-) covalent organic framework, COF-701, directly from acetonitrile, a cheap commodity solvent, by combining/telescoping two consecutive reactions-cyclotrimerization of nitrile and subsequent aldol condensation with aldehydes-in one pot. Acetonitrile is trimerized to generate protonated 2,4,6-trimethyl-s-triazine tautomers in situ, which undergo Aldol condensation with 4,4'-biphenyldicarbaldehyde in one pot to form crystalline COF-701. COF-701 is obtained as a polycrystalline powder and possesses permanent microporosity and a BET surface area (SABET) of 736 m2·g-1. This strategy can be further extended to generate other porous vinylene-linked frameworks.

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Citations

May 19, 2021·Chemistry : a European Journal·Jinwei ZhaoLong Chen
Jun 25, 2021·Chemical Science·Andreas SchneemannStefan Kaskel
Oct 10, 2021·Advanced Materials·Xiaoguang LiangYoonseob Kim

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