Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties - Chimie ORganique & INTerfaces Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2022

Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties

Résumé

Ynamides are useful and versatile building blocks in organic synthesis, from which 1,1,4,4-tetracyanobutadienes (TCBD) can be prepared for application in molecular electronics. However, their insertion onto multi-functional molecular scaffold remains a synthetic challenge. In this work, we report the two-steps synthesis in good isolated yield (64% overall, 89 degrees o stepwise) of a tetraphenylethylene (TPE) bearing four ynamides, and its further one-step conversion into the tetra-TCBD derivative through a [2 + 2] cycloaddition-retroelectrocyclization sequence. The concomitant formation of the four ynamides required a specific optimisation of the reaction conditions. Although a poor fluorescent emitter in solution, the tetra-TCBD compound displayed near-infrared luminescence in the solid state, which is an attractive optoelectronic feature when considering future applications in molecular electronic devices.

Domaines

Chimie
Fichier principal
Vignette du fichier
European J Organic Chem - 2022 - Philippe - Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with.pdf (3.07 Mo) Télécharger le fichier
ejoc202200049-sup-0001-misc_information.pdf (189.67 Ko) Télécharger le fichier
Origine : Publication financée par une institution

Dates et versions

hal-03657696 , version 1 (19-07-2022)

Licence

Paternité - Pas d'utilisation commerciale

Identifiants

Citer

Clotilde Philippe, Maëva Coste, Yann Bretonnière, Loïc Lemiègre, Sebastien Ulrich,, et al.. Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties. European Journal of Organic Chemistry, 2022, 2022 (21), pp.e202200049. ⟨10.1002/ejoc.202200049⟩. ⟨hal-03657696⟩
99 Consultations
39 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More