Indolino-oxazolidine acido and photochromic system investigated by nmr and dft calculations

Guerrin, Clement; Szaloki, Gyorgy; Berthet, Jerome; Sanguinet, Lionel; Orio, Maylis; Delbaere, Stephanie

Document type :

Article dans une revue scientifique: Article original

DOI :

10.1021/acs.joc.8b01482

PMID :

30021066

Permalink :

http://hdl.handle.net/20.500.12210/39840

Title :

Indolino-oxazolidine acido and photochromic system investigated by nmr and dft calculations

Author(s) :

Guerrin, Clement [Auteur]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Szaloki, Gyorgy [Auteur]
Université d'Angers [UA]
Berthet, Jerome [Auteur]

Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Sanguinet, Lionel [Auteur]
Université d'Angers [UA]
Orio, Maylis [Auteur]

Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Delbaere, Stephanie [Auteur]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]

Journal title :

The Journal of organic chemistry

Abbreviated title :

J. Org. Chem.

Publication date :

2018-07-18

ISSN :

1520-6904

HAL domain(s) :

Sciences du Vivant [q-bio]

English abstract : [en]

Three addressable indolino-oxazolidine units connected through an isomerizable double bond to a substituted thiophene represent a smart example of a multiaddressable system whose reversible responses could be selectively ...
Show more >Three addressable indolino-oxazolidine units connected through an isomerizable double bond to a substituted thiophene represent a smart example of a multiaddressable system whose reversible responses could be selectively activated on demand. Experimental and theoretical approaches to push forward the understanding of the system mechanism and set pathways to design optimized compounds for suitable application are here presented. NMR and UV–visible spectroscopies are used for structural and kinetic studies, while density functional theory (DFT) calculations pave the way to highlight energetic and electronic processes that are involved. Substitution and solvent effects toward the reactivity of the compounds are experimentally studied and combined with theoretical calculations. The most efficient and selective stimuli to travel between the four possible states resulting from the ring-opening of indolino[2,1-b]oxazolidine (generally referenced as BOX) derivatives and the trans–cis isomerization of the ethylenic junction are elucidated.Show less >

Language :

Anglais

Audience :

Internationale

Popular science :

Non

Administrative institution(s) :

CHU Lille
IMT Lille Douai
Inserm
Institut Catholique Lille
Univ. Artois
Université de Lille

Collections :

Submission date :

2021-06-23T11:42:17Z
2021-11-16T08:06:55Z
2024-02-21T09:11:45Z

Version	Link	Modification date
3	20.500.12210/39840*	2024-02-21T09:08:58Z
2	20.500.12210/39840.2	2021-11-16T08:05:49Z
1	20.500.12210/39840.1	2021-06-23T11:42:17Z

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Indolino-oxazolidine acido and photochromic ...

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