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The curious case of a sterically crowded Stenhouse salt

05 April 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report a peculiar Stenhouse salt. It does not evolve into cyclopentenones upon basification, due to the steric hindrance of its bulky stable carbene patterns. This allowed for the observation and characterization of the transient open-chain neutral derivative, which was isolated as its cyclized form. The latter features an unusually long reactive C–O bond (150 pm) and a rich electrochemistry, including oxidation into an air-persistent radical cation.

Keywords

cyanine dyes
persistent organic radical
biradicaloid

Supplementary materials

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Description
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Experimental procedures, characterization data and DFT studies.
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Version History

Apr 05, 2022 Version 1

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

DOI

10.26434/chemrxiv-2022-dtnbw
D O I: 10.26434/chemrxiv-2022-dtnbw [opens in a new tab]

Funding

Horizon 2020
Marie Skłodowska-Curie grant No 892162

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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