Issue 39, 2024

Nanohoops in membranes: confined supramolecular spaces within phospholipid bilayer membranes

Abstract

Nanohoops, an exciting class of fluorophores with supramolecular binding abilities, have the potential to become innovative tools within biological imaging and sensing. Given the biological importance of cell membranes, incorporation of macrocyclic materials with the dual capability of fluorescence emission and supramolecular complexation would be particularly interesting. A series of different-sized nanohoops—ethylene glycol-decorated [n]cyclo-para-pyrenylenes (CPYs) (n = 4–8)—were synthesised via an alternate synthetic route which implements a stannylation-based precursor, producing purer material than the previous borylation approach, enabling the growth of single-crystals of the Pt-macrocycle. Reductive elimination of these single-crystals achieved significantly higher selectivity and yields towards smaller ring-sized nanohoops (n = 4–6). The supramolecular binding capabilities of these CPYs were then explored through host–guest studies with a series of polycyclic (aromatic)hydrocarbons, revealing the importance of molecular size, shape, and CH–π contacts for efficient binding. CPYs were incorporated within the hydrophobic layer of lipid bilayer membranes, as confirmed by microscopic imaging and emission spectroscopy, which also demonstrated the size-preferential incorporation of the five-fold nanohoop. Molecular dynamics simulations revealed the position and orientation within the membrane, as well as the unique non-covalent threading interaction between nanohoop and phospholipid.

Graphical abstract: Nanohoops in membranes: confined supramolecular spaces within phospholipid bilayer membranes

Supplementary files

Article information

Article type
Edge Article
Submitted
24 May 2024
Accepted
01 Sep 2024
First published
11 Sep 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 16367-16376

Nanohoops in membranes: confined supramolecular spaces within phospholipid bilayer membranes

K. Chinner, N. Grabicki, R. Hamaguchi, M. Ikeguchi, K. Kinbara, S. Toyoda, K. Sato and O. Dumele, Chem. Sci., 2024, 15, 16367 DOI: 10.1039/D4SC03408B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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