Dithienylethene‐Based Photochromic Siloles: A Straightforward and Divergent Synthetic Strategy

• Published in: Angewandte Chemie International Edition Vol. 60; no. 22; pp. 12356 - 12359
• Main Authors: Devillard, Marc, Nour Eddine, Nour, Cordier, Marie, Alcaraz, Gilles
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 25.05.2021; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Edition: International ed. in English
• Subjects: Alkynes; annulation; catalysis; Chemical reactions; Chemical Sciences; Chemistry; Chemistry, Multidisciplinary; Functional groups; heterocycles; Palladium; photochromes; Photochromism; Physical Sciences; Polymers; Science & Technology; silicon; Substrates; catalysis; annulation; silicon; heterocycles; photochromes
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202102540

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. 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.