Rigidochromism by imide functionalisation of an aminomaleimide fluorophore

Jonathan Husband, Yujie Xie, Thomas Wilks, Louise Male, Miquel Torrent-Sucarrat, Vasilios Stavros, Rachel O'Reilly

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Fluorescent dyes that exhibit high solid state quantum yields and sensitivity to the mechanical properties of their local environment are useful for a wide variety of applications, but are limited in chemical diversity. We report a trityl-functionalised maleimide that displays rigidochromic behaviour, becoming highly fluorescent when immobilised in a solid matrix, while displaying negligible fluorescence in solution. Furthermore, the dye's quantum yield is shown to be sensitive to the nature of the surrounding matrix. Computational studies reveal that this behaviour arises from the precise tuning of inter- and intramolecular noncovalent interactions. This work expands the diversity of molecules exhibiting solid state environment sensitivity, and provides important fundamental insights into their design.
Original languageEnglish
Pages (from-to)10550-10557
Number of pages8
JournalChemical Science
Issue number31
Early online date14 Jul 2021
Publication statusPublished - 21 Aug 2021

Bibliographical note

Funding Information:
The authors thank the Ministerio de Economía y Com-petitividad (MINECO) of Spain (projects CTQ2016-80375-P and PID2019-104772GB-I00), Gobierno Vasco (IT1346-19) and the ERC for support (grant no. 615142). VGS thanks the Royal Society and Leverhulme Trust (LT150052). Dr Robert Keogh is 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.

Publisher Copyright:
© The Royal Society of Chemistry 2021.


  • maleimide
  • rigidochromic
  • fluorescent
  • noncovalent interactions

ASJC Scopus subject areas

  • Chemistry(all)


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