Issue 4, 2024

Insights into extended coupled polymethines through the investigation of dual UV-to-NIR acidochromic switches based on heptamethine–oxonol dyes

Abstract

A series of heptamethine–oxonol dyes featuring different heterocyclic end groups were designed with the aim to explore structure–property relationships in π-extended coupled polymethines. These dyes can be stabilised under three different protonation states, affording dicationic derivatives with an aromatic core, cationic heptamethines, and zwitterionic bis-cyanine forms. The variation of the end groups directly impacts the absorption and emission properties and mostly controls reaching either a colourless neutral dispirocyclic species or near-infrared zwitterions. The acidochromic switching between the three states involves profound electronic rearrangements leading to notable shifts of their optical properties that were investigated using a parallel experiment–theory approach, providing a comprehensive description of these unique systems.

Graphical abstract: Insights into extended coupled polymethines through the investigation of dual UV-to-NIR acidochromic switches based on heptamethine–oxonol dyes

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Article information

Article type
Edge Article
Submitted
15 Nov 2023
Accepted
14 Dez 2023
First published
14 Dez 2023
This article is Open Access

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

Chem. Sci., 2024,15, 1248-1259

Insights into extended coupled polymethines through the investigation of dual UV-to-NIR acidochromic switches based on heptamethine–oxonol dyes

B. Mourot, V. Mazan, M. Elhabiri, R. Sarkar, D. Jacquemin, O. Siri and S. Pascal, Chem. Sci., 2024, 15, 1248 DOI: 10.1039/D3SC06126D

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