Tuning ESIPT fluorophores into dual emitters

Chemical Science
Cloé AzariasDenis Jacquemin

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 s...Continue Reading

References

Jun 1, 1984·Proceedings of the National Academy of Sciences of the United States of America·D McMorrow, M Kasha
Sep 4, 2003·Journal of the American Chemical Society·Wei-Shan YuPi-Tai Chou
Nov 19, 2003·Accounts of Chemical Research·Jacek Waluk
Mar 2, 2005·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Fabiano Severo RodembuschValter Stefani
Aug 12, 2005·Chemical Reviews·Jacopo TomasiRoberto Cammi
Jul 13, 2006·The Journal of Physical Chemistry. a·Adelia J A AquinoChristof Hättig
Feb 20, 2007·Journal of the American Chemical Society·Michał KijakJacek Waluk
Jul 4, 2009·The Journal of Physical Chemistry. a·Felix PlasserHans Lischka
Feb 27, 2010·The Journal of Physical Chemistry. a·Hui-Hsu Gavin TsaiChun-Jui Tan
Aug 25, 2010·Physical Chemistry Chemical Physics : PCCP·Ruifang LiDonald G Truhlar
Mar 30, 2011·Chemical Society Reviews·Jiasheng WuPengfei Wang
Mar 20, 2012·The Journal of Chemical Physics·Sarom S LeangMark S Gordon
Mar 23, 2012·Chemical Communications : Chem Comm·Weihua ChenYi Pang
Sep 5, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Volha VetokhinaJerzy Herbich
May 31, 2013·The Journal of Physical Chemistry. a·Sandra LuberVictor S Batista
Sep 5, 2013·Physical Chemistry Chemical Physics : PCCP·Adina I CiuciuDaniel T Gryko
Sep 21, 2013·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Hossein RoohiMahjobeh Jahantab
Oct 8, 2013·The Journal of Physical Chemistry. a·Catherine G Triandafillou, Spiridoula Matsika
Oct 18, 2013·The Journal of Physical Chemistry. B·Francis A S Chipem, Govindarajan Krishnamoorthy
Nov 21, 2013·The Journal of Physical Chemistry. B·Marika SavareseIlaria Ciofini
Dec 7, 2013·Physical Chemistry Chemical Physics : PCCP·Ymène HouariDenis Jacquemin
Dec 18, 2013·The Journal of Physical Chemistry. a·Lasse SpörkelWalter Thiel
Mar 29, 2014·Physical Chemistry Chemical Physics : PCCP·Marika SavareseIlaria Ciofini
May 2, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Joanna JankowskaAndrzej L Sobolewski
Jun 13, 2014·Organic & Biomolecular Chemistry·Nan JiangChanglin Liu
Oct 23, 2014·Physical Chemistry Chemical Physics : PCCP·Pierre O HubinDenis Jacquemin

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Citations

Sep 25, 2018·Physical Chemistry Chemical Physics : PCCP·Šimon Budzák, Denis Jacquemin
Jan 5, 2019·Physical Chemistry Chemical Physics : PCCP·Pauline M VéritéDenis Jacquemin
May 29, 2019·Physical Chemistry Chemical Physics : PCCP·Leandro D MenaLiliana B Jimenez
Jul 31, 2019·Physical Chemistry Chemical Physics : PCCP·Pauline M VéritéDenis Jacquemin
Apr 14, 2020·Physical Chemistry Chemical Physics : PCCP·Neethu AnandSivaranjana Reddy Vennapusa
Nov 15, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Tolga N V KarsiliMichael N R Ashfold
Jan 7, 2017·Physical Chemistry Chemical Physics : PCCP·Michael Dommett, Rachel Crespo-Otero
Oct 3, 2018·Physical Chemistry Chemical Physics : PCCP·Cristina A Barboza, Andrzej L Sobolewski
Dec 12, 2018·Organic & Biomolecular Chemistry·Bryan J LampkinBrett VanVeller
Dec 17, 2019·Physical Chemistry Chemical Physics : PCCP·Amara ChraytehDenis Jacquemin
Oct 30, 2020·Physical Chemistry Chemical Physics : PCCP·Amara ChraytehDenis Jacquemin
Dec 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maxime MunchGilles Ulrich
Feb 11, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Khanittha KerdpolSupot Hannongbua
Mar 28, 2021·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Kei TogasakiYoshinobu Nishimura
Aug 13, 2020·Angewandte Chemie·Santosh Kumar BeheraJohannes Gierschner
Aug 8, 2021·Materials·Patrícia A A M VazSamuel Guieu
Dec 22, 2016·The Journal of Physical Chemistry. a·Naoko NishinaJun-Ichi Aihara
Jun 16, 2018·Accounts of Chemical Research·Panwang Zhou, Keli Han
Nov 10, 2018·The Journal of Physical Chemistry. a·Quinton J MeisnerLei Zhu
Dec 9, 2017·The Journal of Physical Chemistry Letters·Michael DommettRachel Crespo-Otero
Jun 10, 2016·The Journal of Physical Chemistry. B·Šimon Budzák, Denis Jacquemin

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Software Mentioned

Gaussian09
Turbomole
ESIPT

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