Light-Responsive Pyrazine-Based Systems: Probing Aromatic Diarylethene Photocyclization

Jovana V. Milić, Cédric Schaack, Nora Hellou, Florin Isenrich, Renana Gershoni-Poranne, Dmytro Neshchadin, Sylvain Egloff, Nils Trapp, Laurent Ruhlmann, Corinne Boudon, Georg Gescheidt, Jeanne Crassous, François Diederich

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Here, we present an investigation of the photocyclization of novel aromatic diarylethene (DAE) systems 1-3 based on pyrazine, quinoxaline, and helicene scaffolds. These prospective photoswitches were designed using density functional theory calculations and analyzed in solution and in the solid state by cyclic and rotating disk voltammetry, UV-vis and transient absorption spectroscopy, as well as X-ray crystallography. Additionally, nucleus-independent chemical shift calculations were performed to investigate the influence of aromaticity on the photocyclization ability. While pyrazine-2,3-diyl-extended DAE system 1 demonstrated photoswitching ability with short lifetimes of the cyclized form, the more aromatic quinoxaline analogue 2 did not feature any photocyclization. Further extension of these aromatic systems into helicene-DAE 3 resulted in the stabilization of the cyclized form through the conserved backbone aromaticity, accompanied by enhanced photochromism. This study paves the way toward the generation of aromatic DAE photoswitches for light-controlled molecular systems in the future.

Original languageEnglish
Pages (from-to)19100-19109
Number of pages10
JournalJournal of Physical Chemistry C
Volume122
Issue number33
DOIs
Publication statusPublished - 23 Aug 2018

Fingerprint

Pyrazines
quinoxalines
Quinoxalines
pyrazines
Photochromism
photochromism
X ray crystallography
rotating disks
Rotating disks
Chemical shift
Voltammetry
Absorption spectroscopy
Scaffolds
crystallography
Density functional theory
chemical equilibrium
absorption spectroscopy
Stabilization
stabilization
analogs

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films

Cite this

Milić, J. V., Schaack, C., Hellou, N., Isenrich, F., Gershoni-Poranne, R., Neshchadin, D., ... Diederich, F. (2018). Light-Responsive Pyrazine-Based Systems: Probing Aromatic Diarylethene Photocyclization. Journal of Physical Chemistry C, 122(33), 19100-19109. https://doi.org/10.1021/acs.jpcc.8b05019

Light-Responsive Pyrazine-Based Systems : Probing Aromatic Diarylethene Photocyclization. / Milić, Jovana V.; Schaack, Cédric; Hellou, Nora; Isenrich, Florin; Gershoni-Poranne, Renana; Neshchadin, Dmytro; Egloff, Sylvain; Trapp, Nils; Ruhlmann, Laurent; Boudon, Corinne; Gescheidt, Georg; Crassous, Jeanne; Diederich, François.

In: Journal of Physical Chemistry C, Vol. 122, No. 33, 23.08.2018, p. 19100-19109.

Research output: Contribution to journalArticleResearchpeer-review

Milić, JV, Schaack, C, Hellou, N, Isenrich, F, Gershoni-Poranne, R, Neshchadin, D, Egloff, S, Trapp, N, Ruhlmann, L, Boudon, C, Gescheidt, G, Crassous, J & Diederich, F 2018, 'Light-Responsive Pyrazine-Based Systems: Probing Aromatic Diarylethene Photocyclization' Journal of Physical Chemistry C, vol. 122, no. 33, pp. 19100-19109. https://doi.org/10.1021/acs.jpcc.8b05019
Milić, Jovana V. ; Schaack, Cédric ; Hellou, Nora ; Isenrich, Florin ; Gershoni-Poranne, Renana ; Neshchadin, Dmytro ; Egloff, Sylvain ; Trapp, Nils ; Ruhlmann, Laurent ; Boudon, Corinne ; Gescheidt, Georg ; Crassous, Jeanne ; Diederich, François. / Light-Responsive Pyrazine-Based Systems : Probing Aromatic Diarylethene Photocyclization. In: Journal of Physical Chemistry C. 2018 ; Vol. 122, No. 33. pp. 19100-19109.
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