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

1 Citation (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

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

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@article{d279a80008ba4f94a4e275a0e63719d1,

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.",

keywords = "aminochloromaleimide, dual-state emission, fluorocarbons, maleimide fluorophores, monoaminomaleimide",

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. ",

year = "2022",

month = oct,

day = "18",

doi = "10.1002/chem.202201877",

language = "English",

volume = "28",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-Blackwell",

number = "58",

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TY - JOUR

T1 - Enhancing Dual-State Emission in Maleimide Fluorophores through Fluorocarbon Functionalisation

AU - Pervez, Maria

AU - Pearce, Amanda K.

AU - Husband, Jonathan T.

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.

KW - aminochloromaleimide

KW - dual-state emission

KW - fluorocarbons

KW - maleimide fluorophores

KW - monoaminomaleimide

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U2 - 10.1002/chem.202201877

DO - 10.1002/chem.202201877

M3 - Article

AN - SCOPUS:85136482343

SN - 0947-6539

VL - 28

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 58

M1 - e202201877

ER -

Enhancing Dual-State Emission in Maleimide Fluorophores through Fluorocarbon Functionalisation

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Keywords

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