Issue 3, 2019

Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the cavities of site-specifically modified indolocarbazole-pyridine foldamers

Abstract

Indolocarbazole-Pyridine (IP) hybrid foldamers have been known to adopt a helical conformation with an internal tubular cavity wherein water molecules are tightly packed via the formation of multiple cooperative hydrogen bonds. In order to develop IP foldamer-based receptors for ions and molecules other than water molecules, we herein prepare two modified IP foldamers 2 and 3 that contain a pyrrole and an inverted pyridine in the middle of the strands, respectively, instead of the original pyridine unit. Such site-specific modification significantly disrupts the hydrogen-bonding network between the entrapped water molecules and the interior of the cavity, thus allowing for binding two dihydrogenphosphate ions as a cyclic dimer inside the cavity as demonstrated by 1H NMR spectroscopy and X-ray crystal structure analysis. The crystal structures of the two complexes (H2PO4)22 and (H2PO4)23 are very similar to each other, with twelve hydrogen bonds between the bound dihydrogenphosphate dimer and the interior functional groups, indolocarbazole NH protons, pyridine nitrogen atoms and terminal OH protons in the helical tubular cavity.

Graphical abstract: Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the cavities of site-specifically modified indolocarbazole-pyridine foldamers

Supplementary files

Article information

Article type
Research Article
Submitted
27 ربيع الأول 1440
Accepted
20 ربيع الثاني 1440
First published
21 ربيع الثاني 1440

Org. Chem. Front., 2019,6, 299-303

Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the cavities of site-specifically modified indolocarbazole-pyridine foldamers

C. Lee, H. Lee, S. Lee, H. Jeon and K. Jeong, Org. Chem. Front., 2019, 6, 299 DOI: 10.1039/C8QO01307A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements