6-(Arylvinylene)-3-bromopyridine Derivatives as Lego Building Blocks for Liquid Crystal, Nonlinear Optical, and Blue Light Emitting Chromophores

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• 作者：Nicolas Leclerc ; Sé ; bastien Sanaur ; Laurent Galmiche ; Fabrice Mathevet ; André ; -Jean Attias ; Jean-Louis Fave ; Joseph Roussel ; Philippe Hapiot ; No&euml ; lla Lemaî ; tre ; and Bernard Geffro
• 刊名：Chemistry of Materials
• 出版年：2005
• 出版时间：February 8, 2005
• 年：2005
• 卷：17
• 期：3
• 页码：502 - 513
• 全文大小：601K
• 年卷期：v.17,no.3(February 8, 2005)
• ISSN：1520-5002

文摘

A novel general synthetic strategy, based on a convergent approach, allowed us to prepare a series ofconjugated 6,6'-distyryl-3,3'-bipyridine derivatives via the Suzuki reaction. First, the key electron-donorand electron-acceptor 6-(arylvinylene)-3-bromopyridine building blocks were synthesized by Knoevenagel-or Siegrist-type reactions. Second, some of them were transformed to the corresponding pyridylboronicesters. Finally, for the first time, we successfully demonstrated that such blocks can be homo- and cross-coupled in high yields and multigram scales, leading to noncentrosymmetic or symmetric chromophores.Their mesogenic, electrochemical, and optical properties have been investigated depending on the electronicstructure. In this series, push-pull compounds are liquid crystals and promising for NLO applications.Whatever the structure, all of these compounds exhibit a high electron affinity and are strongly fluorescent.As an application, lasing properties of one push-pull and one symmetrical compound are reported. Inaddition, a blue-emitting LED was fabricated whose performances at 10 mA/cm² are a luminous efficiencyof 3.9 cd/A, a power efficiency of 1.4 lm/W, and an external quantum efficiency of 2.9%. Thus, thisversatile synthetic route is of particular interest due to the potential applications of the chromophores inseveral optoelectronic fields.