Issue 7, 2023

2D self-assembly of o-OPE foldamers for chiroptical barcoding

Abstract

We report on the preparation and characterization of two dimensional (2D) films of (S,S,P)-1 and (R,R,M)-1ortho-oligophenylene ethylene (o-OPE) enantiomers presenting high values of circularly polarized luminescence (CPL). The amphiphilic character of these two molecules allows a precise 2D self-assembly at the air/water interface and an efficient transfer onto a glass solid support. The morphological and chiroptical characterization of the solid supports after the transfer of 1, 8, 16 and 32 Langmuir films of (S,S,P)-1 and (R,R,M)-1 has been carried out. The strong chiroptical values of these monomers allow reliable ECD measurements to be obtained after a single transfer, with ECD values increasing as the number of transferred films increases. The semi-liquid behavior of the monomers on the solid substrate allows CPL measurements free of photoselection artifacts that show values similar to those obtained in solution and independent of monomer concentration. All these properties have allowed us to develop the first simple organic molecule (SOM)-based chiroptical barcoding presenting positive and negative regions as a proof of concept.

Graphical abstract: 2D self-assembly of o-OPE foldamers for chiroptical barcoding

Supplementary files

Article information

Article type
Paper
Submitted
07 12 2022
Accepted
24 1 2023
First published
24 1 2023
This article is Open Access
Creative Commons BY-NC license

J. Mater. Chem. C, 2023,11, 2591-2599

2D self-assembly of o-OPE foldamers for chiroptical barcoding

I. López-Sicilia, A. M. Ortuño, P. Reine, D. Otero, M. T. Martín-Romero, L. Camacho, L. Álvarez de Cienfuegos, A. Orte, J. J. Giner-Casares, D. Miguel and J. M. Cuerva, J. Mater. Chem. C, 2023, 11, 2591 DOI: 10.1039/D2TC05208C

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