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Competitive Aminal Formation during the Synthesis of a Highly Soluble, Isopropyl-Decorated Imine Porous Organic Cage

05 January 2023, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The synthesis of a new porous organic cage decorated with isopropyl moieties (CC21) was achieved from the reaction of triformylbenzene and an isopropyl functionalised diamine. Unlike structurally analogous porous organic cages, its synthesis proved challenging due to competitive aminal formation, rationalised using control experiments and computational modelling. The use of an additional amine was found to increase conversion to the desired cage.

Keywords

Porous organic cages
Dynamic covalent chemistry

Supplementary materials

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Includes experimental procedures, characterisation data, and computational details.
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Version History

Jan 05, 2023 Version 1

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-cn4q1
D O I: 10.26434/chemrxiv-2023-cn4q1 [opens in a new tab]

Funding

Engineering and Physical Sciences Research Council (EPSRC)
EP/R005710/1
Engineering and Physical Sciences Research Council (EPSRC)
EP/W01601X/1
The Royal Society
University Research Fellowships
European Research Council under FP7
CoMMaD, ERC Grant No. 758370
The Royal Society
Enhancement Award 2018
Engineering and Physical Sciences Research Council (EPSRC)
ARCHER2 UK National Supercomputing Service via the UK′s HEC Materials Chemistry Consortium (EP/L000202, EP/R029431, EP/T022213)

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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