Upgrading Cyanines dyes: Non-Kekulé ketocyanines and related patterns

Información del proyecto

KETOCYAN

Identificador del acuerdo de subvención: 892162

DOI

10.3030/892162

Proyecto finalizado el 31 Diciembre 2021

Fecha de la firma de la CE 28 Marzo 2020

Fecha de inicio 1 Agosto 2020

Fecha de finalización 31 Julio 2022

Financiado con arreglo a

• EXCELLENT SCIENCE - Marie Skłodowska-Curie Actions

Coste total

€ 184 707,84

Aportación de la UE

€ 184 707,84

Coordinado por

UNIVERSITE GRENOBLE ALPES
France

Periodic Reporting for period 1 - KETOCYAN (Upgrading Cyanines dyes: Non-Kekulé ketocyanines and related patterns)

Período documentado: 2020-08-01 hasta 2022-07-31

Resumen del contexto y de los objetivos generales del proyecto

The goal of KETOCYAN project is to develop a library of novel diradicaloid dyes (so-called non-Kekulé ketocyanines), as well as related highly persistent radical species. Most of these exotic molecules have long been disregarded unrealistic propositions due to their unusual structures; however, they are expected to possess intriguing physical and chemical properties, with potential in the fields of optoelectronics and photoredox chemistry. The development of unorthodox organic functionalities mostly aims at academic breakthroughs, but as history has proven itself in countless ways the discovery of unconventional molecules paves the way to major technological advances and potentially commercially uses.

Trabajo realizado desde el comienzo del proyecto hasta el final del período abarcado por el informe y los principales resultados hasta la fecha

The study of a first set of precursors indicated the key role of steric hindrance in the viability of the targets. These preliminary results opened two research lines.
The first one covered the design of unprecedented versions of dyes, known as “Stenhouse salts”. And allowed for the observation and spectroscopic characterization for the first time of an electronically non-stabilized non-Kekulé ketocyanine at low temperature. A seminal paper on this work is of imminent submission during the first trimester of 2022.
Electrochemical investigations of other precursors also unveiled a second research line, providing promising guidelines for the isolation of targeted dyes at room temperature. Closely related models were also used for a side study, which was part of the training of the fellow in electrochemistry. This work unveiled critical misconceptions in the mechanism of important biomimetic radical transformations. (see: L. Delfau, S. Nichilo, F. Molton, J. Broggi, E. Tomás-Mendivil,* D. Martin* Angew. Chem. Int. Ed. 2021, 60, 26783-26789.).

Avances que van más allá del estado de la técnica e impacto potencial esperado (incluida la repercusión socioeconómica y las implicaciones sociales más amplias del proyecto hasta la fecha)

This action has contributed to look beyond the edge of modern organic chemical knowledge and intuition by introducing unconventional and original compounds with unusual electronic structures. The study supports the hypothesis that the isolation of room temperature stable non-Kekulé ketocyanine dyes is feasible. It also brings alternative synthetic strategies for the development of original dyes. The discovery of such compounds may or may not lead to future applications; however, the novel molecules and concepts that are/will be publish open a research line of promising future.
The action had an impact in different spheres of academy and society. Undergraduate and graduate students among other has benefited from the expertise brought by the fellow, through direct supervision, but also by discussing ideas throughout the daily work. Public engagement activities with high school students by sharing basic concepts in chemistry and his enthusiasm have become part of the action. The integration within the institution has been successfully accomplished and the action has undoubtedly contributed to his recruitment as a permanent researcher where he is committed to science and outreach.

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