Enhancing Dual-State Emission in Maleimide Fluorophores through Fluorocarbon Functionalisation

Maria Pervez; Amanda K. Pearce; Jonathan T. Husband; Louise Male; Miquel Torrent-Sucarrat; Rachel K. O'Reilly

doi:10.1002/chem.202201877

Enhancing Dual-State Emission in Maleimide Fluorophores through Fluorocarbon Functionalisation

Maria Pervez, Amanda K. Pearce, Jonathan T. Husband, Louise Male, Miquel Torrent-Sucarrat, Rachel K. O'Reilly

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

13 Citations (SciVal)

Abstract

Herein, a library of trifluoroethyl substituted aminomaleimide derivatives are reported with small size and enhanced emissions in both solution and solid-state. A diCH₂CF₃ substituted aminochloromaleimide exhibits the most efficient dual-state emission (Φ_f >50 % in solution and solid-state), with reduced quenching from protic solvents. This is attributed to the reduction of electron density on the maleimide ring and suppressed π-π stacking in the solid-state. This mechanism was explored in-depth by crystallographic analysis, and modelling of the electronic distribution of HOMO-LUMO isosurfaces and NCI plots. Hence, these dual-state dyes overcome the limitations of single-state luminescence and will serve as an important step forward for this rapidly developing nascent field.

Original language	English
Article number	e202201877
Journal	Chemistry - A European Journal
Volume	28
Issue number	58
Early online date	20 Jul 2022
DOIs	https://doi.org/10.1002/chem.202201877
Publication status	Published - 18 Oct 2022

Bibliographical note

Funding Information:
The authors thank the Ministerio de Economía y Competitividad (MINECO) of Spain (project: PID2019-104772GB-I00) and the Basque Government (project IT1346-19), and the Leverhulme Trust (RPG-2016-452). Dr. Thomas R. Wilks and Dr. Yujie Xie are thanked for helpful discussions and Chi Tsang (University of Birmingham) for high resolution mass spectroscopy analysis. The authors acknowledge the computational resources, and technical and human support provided by the DIPC.

Funding

The authors thank the Ministerio de Economía y Competitividad (MINECO) of Spain (project: PID2019-104772GB-I00) and the Basque Government (project IT1346-19), and the Leverhulme Trust (RPG-2016-452). Dr. Thomas R. Wilks and Dr. Yujie Xie are thanked for helpful discussions and Chi Tsang (University of Birmingham) for high resolution mass spectroscopy analysis. The authors acknowledge the computational resources, and technical and human support provided by the DIPC.

Keywords

aminochloromaleimide
dual-state emission
fluorocarbons
maleimide fluorophores
monoaminomaleimide

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.202201877Licence: CC BY-NC

Cite this

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title = "Enhancing Dual-State Emission in Maleimide Fluorophores through Fluorocarbon Functionalisation",

abstract = "Herein, a library of trifluoroethyl substituted aminomaleimide derivatives are reported with small size and enhanced emissions in both solution and solid-state. A diCH2CF3 substituted aminochloromaleimide exhibits the most efficient dual-state emission (Φf >50 % in solution and solid-state), with reduced quenching from protic solvents. This is attributed to the reduction of electron density on the maleimide ring and suppressed π-π stacking in the solid-state. This mechanism was explored in-depth by crystallographic analysis, and modelling of the electronic distribution of HOMO-LUMO isosurfaces and NCI plots. Hence, these dual-state dyes overcome the limitations of single-state luminescence and will serve as an important step forward for this rapidly developing nascent field.",

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author = "Maria Pervez and Pearce, {Amanda K.} and Husband, {Jonathan T.} and Louise Male and Miquel Torrent-Sucarrat and O'Reilly, {Rachel K.}",

note = "Funding Information: The authors thank the Ministerio de Econom{\'i}a y Competitividad (MINECO) of Spain (project: PID2019-104772GB-I00) and the Basque Government (project IT1346-19), and the Leverhulme Trust (RPG-2016-452). Dr. Thomas R. Wilks and Dr. Yujie Xie are thanked for helpful discussions and Chi Tsang (University of Birmingham) for high resolution mass spectroscopy analysis. The authors acknowledge the computational resources, and technical and human support provided by the DIPC. ",

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AU - Male, Louise

AU - Torrent-Sucarrat, Miquel

AU - O'Reilly, Rachel K.

N1 - Funding Information: The authors thank the Ministerio de Economía y Competitividad (MINECO) of Spain (project: PID2019-104772GB-I00) and the Basque Government (project IT1346-19), and the Leverhulme Trust (RPG-2016-452). Dr. Thomas R. Wilks and Dr. Yujie Xie are thanked for helpful discussions and Chi Tsang (University of Birmingham) for high resolution mass spectroscopy analysis. The authors acknowledge the computational resources, and technical and human support provided by the DIPC.

PY - 2022/10/18

Y1 - 2022/10/18

N2 - Herein, a library of trifluoroethyl substituted aminomaleimide derivatives are reported with small size and enhanced emissions in both solution and solid-state. A diCH2CF3 substituted aminochloromaleimide exhibits the most efficient dual-state emission (Φf >50 % in solution and solid-state), with reduced quenching from protic solvents. This is attributed to the reduction of electron density on the maleimide ring and suppressed π-π stacking in the solid-state. This mechanism was explored in-depth by crystallographic analysis, and modelling of the electronic distribution of HOMO-LUMO isosurfaces and NCI plots. Hence, these dual-state dyes overcome the limitations of single-state luminescence and will serve as an important step forward for this rapidly developing nascent field.

AB - Herein, a library of trifluoroethyl substituted aminomaleimide derivatives are reported with small size and enhanced emissions in both solution and solid-state. A diCH2CF3 substituted aminochloromaleimide exhibits the most efficient dual-state emission (Φf >50 % in solution and solid-state), with reduced quenching from protic solvents. This is attributed to the reduction of electron density on the maleimide ring and suppressed π-π stacking in the solid-state. This mechanism was explored in-depth by crystallographic analysis, and modelling of the electronic distribution of HOMO-LUMO isosurfaces and NCI plots. Hence, these dual-state dyes overcome the limitations of single-state luminescence and will serve as an important step forward for this rapidly developing nascent field.

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KW - fluorocarbons

KW - maleimide fluorophores

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Enhancing Dual-State Emission in Maleimide Fluorophores through Fluorocarbon Functionalisation

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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