When Light and Acid Play Tic-Tac-Toe with a Nine-State Molecular Switch.

Autor: Guerrin C; Université de Lille, CNRS, UMR 8516, LASIR , Laboratoire de Spectrochimie Infra-rouge et Raman , F-59000 Lille , France., Aidibi Y; MOLTECH-Anjou, UMR 6200, CNRS , UNIV Angers , 2 bd Lavoisier , 49045 Angers Cedex France., Sanguinet L; MOLTECH-Anjou, UMR 6200, CNRS , UNIV Angers , 2 bd Lavoisier , 49045 Angers Cedex France., Leriche P; MOLTECH-Anjou, UMR 6200, CNRS , UNIV Angers , 2 bd Lavoisier , 49045 Angers Cedex France., Aloise S; Université de Lille, CNRS, UMR 8516, LASIR , Laboratoire de Spectrochimie Infra-rouge et Raman , F-59000 Lille , France., Orio M; Aix Marseille Univ, CNRS, Centrale Marseille , iSm2 , Marseille , France., Delbaere S; Université de Lille, CNRS, UMR 8516, LASIR , Laboratoire de Spectrochimie Infra-rouge et Raman , F-59000 Lille , France.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2019 Dec 04; Vol. 141 (48), pp. 19151-19160. Date of Electronic Publication: 2019 Nov 22.
DOI: 10.1021/jacs.9b11048
Abstrakt: Combining different molecular switching functions in a single molecule is a simple strategy to develop commutable molecules featuring more than two commutation states. The present study reports on two molecular systems consisting of two indolino-oxazolidine (Box) moieties connected to an aromatic bridge (phenyl or bithiophene) by ethylenic junctions. Such systems, referenced as BiBox, are expected to show up multiaddressable and multiresponsive behaviors. On one hand, the oxazolidine ring opening/closure of Box moieties can be addressed by chemical stimuli, and on the other hand, the trans-to-cis isomerization of the ethylenic junctions is induced by visible light irradiation (with a thermal back conversion). NMR and UV-visible spectroscopies allowed to characterize up to nine out of the ten theoretically expected commutation states as well as to measure the kinetics of the interconversions. Also, steady state fluorescence spectroscopy measurements highlighted the strong influence of the open/closed states of the Box moieties on their emission properties.
Databáze: MEDLINE