Rigidochromism by imide functionalisation of an aminomaleimide fluorophore |
| |
Authors: | Jonathan T. Husband Yujie Xie Thomas R. Wilks Louise Male Miquel Torrent-Sucarrat Vasilios G. Stavros Rachel K. O'Reilly |
| |
Affiliation: | School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT UK.; Department of Organic Chemistry I, Universidad del País Vasco (UPV/EHU), Donostia International Physics Center (DIPC), Manuel Lardizabal Ibilbidea 3, Donostia 20018 Spain ; Ikerbasque, Basque Foundation for Science, Plaza Euskadi 5, 48009 Bilbao Euskadi Spain ; Department of Chemistry, University of Warwick, Coventry CV4 8AL UK |
| |
Abstract: | 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.In this study, by systematic tuning of imide substituent a maleimides dye with sensitivity to its solid-state environment was investigated. |
| |
Keywords: | |
|
|