ja0c04570_si_001.pdf (1.38 MB)
Synthesis of Vinylene-Linked Covalent Organic Frameworks from Acetonitrile: Combining Cyclotrimerization and Aldol Condensation in One Pot
journal contribution
posted on 2020-08-06, 22:19 authored by Amitava Acharjya, Lewis Longworth-Dunbar, Jérôme Roeser, Pradip Pachfule, Arne ThomasCombining
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 (−CHCH−)
covalent organic framework, COF-701, directly from acetonitrile,
a cheap commodity solvent, by combining/telescoping two consecutive
reactionscyclotrimerization of nitrile and subsequent aldol
condensation with aldehydesin 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.