Cambridge Open Engage home
What is Cambridge Open Engage?
How to Submit
Browse
About
News [opens in a new tab]

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

Title
Description
Actions
Title
Electronic Supplementary Information (ESI)
Description
Experimental procedures, characterization data and DFT studies.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

Version History

Apr 05, 2022 Version 1

Metrics

411
247
0
Views
Downloads
Citations

License

CC logo
CC
BY logo
BY
NC logo
NC
ND logo
ND
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

Share