Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 22nd May 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 6, 2016
Previous Article Next Article

Tuning ESIPT fluorophores into dual emitters

Author affiliations

Abstract

Dyes undergoing excited-state intramolecular proton transfer (ESIPT) are known to present large Stokes shifts as a result of the important geometrical reorganisation following photon absorption. When the ESIPT process is not quantitative, one can obtain dual emitters characterised by two distinct fluorescence bands, observed due to emissions from both the canonical and ESIPT isomers. However, dual emission generally requires to maintain a very specific balance, as the relative excited-state free energies of the two tautomers have to be within a narrow window to observe the phenomenon. Consequently, simple chemical intuition is insufficient to optimise dual emission. In the present contribution, we investigate, with the help of quantum-mechanical tools and more precisely, time-dependent density functional theory (TD-DFT) and algebraic diagrammatic construction (ADC), a wide panel of possible ESIPT/dual emitters with various substituents. The selected protocol is first shown to be very robust on a series of structures with known experimental behaviour, and next is applied to novel derivatives with various substituents located at different positions. This work encompasses the largest chemical library of potential ESIPT compounds studied to date. We pinpoint the most promising combinations for building dual emitters, highlight unexpected combination effects and rationalise the impact of the different auxochromes.

Graphical abstract: Tuning ESIPT fluorophores into dual emitters

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Dec 2015, accepted on 23 Feb 2016 and first published on 23 Feb 2016


Article type: Edge Article
DOI: 10.1039/C5SC04826E
Author version
available:
Download author version (PDF)
Chem. Sci., 2016,7, 3763-3774
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Tuning ESIPT fluorophores into dual emitters

    C. Azarias, Š. Budzák, A. D. Laurent, G. Ulrich and D. Jacquemin, Chem. Sci., 2016, 7, 3763
    DOI: 10.1039/C5SC04826E

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements