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

Guest-induced misfolding of a crown-ether-functionalized ortho-phenylene

25 October 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A crown-ether-functionalized o-phenylene tetramer has been synthesized and co-assembled with monotopic and ditopic, achiral and chiral secondary ammonium ion guests. NMR spectroscopy shows that the o-phenylene forms both 1:1 and 1:2 complexes with monotopic guests while remaining well-folded. Binding of an elongated ditopic guest, however, forces the o-phenylene to misfold by pulling the terminal rings apart. A chiral ditopic guest biases the o-phenylene twist sense.

Keywords

foldamers
host-guest
crown ethers

Supplementary materials

Title
Description
Actions
Title
Supporting information for "Guest-induced misfolding of a crown-ether-functionalized ortho-phenylene"
Description
Supplemental figures, NMR spectra, UV-vis and CD spectra, computational chemistry data
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.

Now Published

Guest-Driven Control of Folding in a Crown-Ether-Functionalized ortho-Phenylene [opens in a new tab]
Sumalatha Peddi, Molly C. Bookout, Gopi Nath Vemuri, C. Scott Hartley journal article
The Journal of Organic Chemistry , Volume 87, Issue 5
Online publication date: Jan 13, 2022

Version History

Oct 25, 2021 Version 1

Metrics

654
255
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-2021-r4dlq
D O I: 10.26434/chemrxiv-2021-r4dlq [opens in a new tab]

Funding

National Science Foundation
CHE-1608213
National Science Foundation
CHE-1904236

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