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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

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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
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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

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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

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