6-(Arylvinylene)-3-pyridinylboronic esters. Part 2: Versatile building blocks for push–pull nonlinear optical chromophores

✍ Scribed by Nicolas Leclerc; Laurent Galmiche; André-Jean Attias

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 267 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01427-8

✦ Synopsis

This paper describes a general approach for the synthesis of push-pull 6,6%-disubstituted-3,3%-bipyridine chromophores. As examples, 6-(4-ethanol-2-thienylvinylene)-5-methyl-3-bromopyridine, 6-(4-hydroxy-phenylvinylene)-5-methyl-3-bromopyridine, and the corresponding 3-pyridinylboronic esters have been prepared as building blocks end-capped with electron donor groups (D). 6-(4-Cyano-phenylvinylene)-5-methyl-3-bromopyridine, and 6-(4-cyano-phenylvinylene)-3-bromopyridine have been synthesized as building blocks end-capped with electron acceptor groups (A). {A x D} type cross-couplings via Suzuki reaction gave the push-pull chromophores (I) and (II) in high yields and multigram scales.