Dithienylethene‐Based Photochromic Siloles: A Straightforward and Divergent Synthetic Strategy. (21st April 2021)

• Record Type: Journal Article
• Authors: Devillard, Marc; Nour Eddine, Nour; Cordier, Marie; Alcaraz, Gilles
• Is Part Of: Angewandte Chemie. Volume 133:Number 22(2021)
• Page Start: 12464
• Page End: 12467
• Publication Date: 2021-04-21
• Subjects: annulation -- catalysis -- heterocycles -- photochromes -- silicon; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202102540
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A straightforward synthetic methodology for the preparation of photochromic siloles based on the dithienylethene motif is developed. It relies upon an efficient palladium‐catalyzed annulation reaction of a 2, 3‐bis(3‐thienyl)‐silirene with terminal alkynes in mild conditions. The reaction is functional group‐tolerant and can be performed in high yields with a variety of functional terminal alkynes. It can even be extended to a polymeric polypropargylmethacrylamide (PPMA) substrate affording the corresponding photochromic polymer with different degree of photochromic unit incorporation by simply adjusting the polymer/ silirene stoichiometric ratio. Abstract : A straightforward preparation of photochromic siloles based on the dithienylethene motif is developed. It relies upon an efficient palladium‐catalyzed annulation reaction of a 2, 3‐bis(3‐thienyl)‐silirene with terminal alkynes in mild conditions. The reaction is functional group‐tolerant and can be performed in high yields with a variety of functional terminal alkynes.