Rational Design of Push–Pull Fluorene Dyes: Synthesis and Structure–Photophysics Relationship

Janah Shaya, Fabien Fontaine-Vive, Benoît Y. Michel, Alain Burger

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

Our work surveyed experimental and theoretical investigations to construct highly emissive D–π–A (D=donor, A=acceptor) fluorenes. The synthetic routes were optimised to be concise and gram-scalable. The molecular design was first rationalised by varying the electron-withdrawing group from an aldehyde, ketotriazole or succinyl to methylenemalonitrile or benzothiadiazole. The electron-donating group was next varied from aliphatic or aromatic amines to saturated cyclic amines ranging from aziridine to azepane. Spectroscopic studies correlated with TD-DFT calculations provided the optimised structures. The selected push–pull dyes exhibited visible absorptions, significant brightness, important solvatofluorochromism, mega-Stokes shifts (>250 nm) and dramatic shifts in emission to the near-infrared. The current library includes the comprehensive characterization of 16 prospective dyes for fluorescence applications. Among them, several fluorene derivatives bearing different conjugation anchors were tested for coupling and demonstrated to preserve the photophysical responses once further bound.

Original languageBritish English
Pages (from-to)10627-10637
Number of pages11
JournalChemistry - A European Journal
Volume22
Issue number30
DOIs
StatePublished - 18 Jul 2016

Keywords

  • Buchwald–Hartwig amination
  • charge transfer
  • fluorescent probes
  • push–pull fluorenes
  • structure–photophysics relationship

Fingerprint

Dive into the research topics of 'Rational Design of Push–Pull Fluorene Dyes: Synthesis and Structure–Photophysics Relationship'. Together they form a unique fingerprint.

Cite this