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Insights into extended coupled polymethines through the investigation of dual UV-to-NIR acidochromic switches based on heptamethine–oxonol dyes†
a
Valérie
Mazan,
b
Mourad
Elhabiri,
b
Rudraditya
Sarkar,
cd
Denis
Jacquemin,
*ce
Olivier
Siri
a
and
Simon
Pascal
*ac
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.
- This article is part of the themed collections: 2024 Chemical Science Covers and 2023 Chemical Science HOT Article Collection
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