An updated synthesis of octa-acid

Octa-acid 1 is a water-soluble cavitand that has been used to investigate hydrophobic solvation and Hofmeister effects, control photophysical and physicochemical properties, modulate the reactivity of encapsulated guests, and as a tool to engender novel separation protocols. The synthesis of 1 has l...

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Bibliographic Details
Published in:Supramolecular chemistry 2023-12, Vol.34 (11-12), p.480-483
Main Authors: Gibb, Corinne L. D., Hebert, André J., Ismaiel, Yahya A., Prusty, Priyanka, Wyshel, Theodore, Gibb, Bruce C.
Format: Article
Language:English
Subjects:
Aqueous solution
host
Purity
Solvation
supramolecular chemistry
Synthesis
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Summary:Octa-acid 1 is a water-soluble cavitand that has been used to investigate hydrophobic solvation and Hofmeister effects, control photophysical and physicochemical properties, modulate the reactivity of encapsulated guests, and as a tool to engender novel separation protocols. The synthesis of 1 has largely centered around its formation from 2, a host that is itself most readily synthesized on the multi-gram-scale in crude form (>75% purity). In this Methods Article we reveal improvements in the synthesis of 2, as well as a new synthetic strategy that efficiently converts crude 2 into pure 1. This provides access to 1 in only a five-step linear sequence, shortening the total reaction time from previous methods, improving the purity, and increasing the final yield of 1. We therefore anticipate that the described protocols will be of interest to researchers seeking to utilize octa-acid in their studies.
ISSN:1061-0278
1029-0478
DOI:10.1080/10610278.2024.2379347