New Functionalized Indoles: Synthesis and Potential Applications

• Main Author: 張許永
• Other Authors: 胡紀如
• Format: Others
• Published: 2004
• Online Access: http://ndltd.ncl.edu.tw/handle/60210832671868247385

碩士 === 國立清華大學 === 化學系 === 92 === A series of new multi-functionalized indoles were designed and synthesized as blue-light emitting materials. Palladium-catalyzed coupling of methyl (3,4-dimethoxyphenyl)propiolates or a 9-anthraldehyde with 4-substituted-2-iodo-1- anilines in the presence of n-Bu4NBr (1.0 equiv) and NaOAc in DMF at 100–120 °C afforded the new indoles 1a–g and 13a,b, respectively, in 25–65% yields. Fine tune of their blue electroluminescence was performed by placement of elelctron-donating and -withdrawing substitutents at the C2-, C3-, and C5-positions. The quantum yields were measured between 0.41 and 0.59 by use of anthracene as the reference. These indole derivatives melted around 200 °C and were stable up to 250 °C. Results from spectroscopic measurements, molecular computations, and device manufacture indicate that the blue color of indoles can be successfully shifted to the desired chromaticity coordiates.