College of Chemistry, Beijing Normal University, Beijing 100875, China.
Org Biomol Chem. 2011 Apr 7;9(7):2166-74. doi: 10.1039/c0ob00746c. Epub 2011 Feb 4.
A study on the multicomponent reaction comprising both N-heterocyclic carbenes and substituted phthalaldehydes is reported. The imidazo[1,5-a]pyridine carbenes, namely imidazo[1,5-a]pyridine-3-ylidenes, reacted with phthalaldehydes and DMAD under very mild conditions to produce novel fused tricyclic benzo[d]furo[3,2-b]azepine derivatives. The resulting fused heterocyclic compounds are fluorescent and they give an emission around 500 nm with quantum yields (Φ(F)) being up to 0.81. This study provides not only a unique approach to fused azepine derivatives that are not easily accessible by other methods, but also opens a new avenue to complicated molecular skeletons. The fluorescence properties of long emission wavelength and high fluorescence quantum yields of some products predict their potential applications as optical sensors.
本文报道了一种涉及 N-杂环卡宾和取代邻苯二甲醛的多组分反应的研究。咪唑并[1,5-a]吡啶卡宾，即咪唑并[1,5-a]吡啶-3-亚基，在非常温和的条件下与邻苯二甲醛和 DMAD 反应，生成了新型稠合三环苯并[d]呋喃并[3,2-b]氮杂卓衍生物。所得稠合杂环化合物具有荧光性质，其发射波长在 500nm 左右，荧光量子产率（Φ(F)）高达 0.81。该研究不仅为其他方法不易获得的稠合氮杂卓衍生物提供了一种独特的方法，而且为复杂分子骨架开辟了新途径。一些产物具有长发射波长和高光荧光量子产率的荧光性质，预示着它们在光学传感器方面的潜在应用。
