Azulene-Indole Fused Polycyclic Heteroaromatics |
| |
| Authors: | Chao Duan Jianwei Zhang Shali Cai Junjun Xiang Prof. Xiaodi Yang Prof. Xike Gao |
| |
| Affiliation: | 1. Key Laboratory of Synthetic and Self-Assembly Chemistry, for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032 China;2. Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203 China |
| |
| Abstract: | Linear polycyclic systems are promising candidates in the area of organic electronics. Herein, we present the syntheses of three azulene-indole (AzIn) fused polycyclic heteroaromatics (PHAs), AzIn - 1 , AzIn - 2 and DGAzIn , which have nitrogens and nonhexagonal rings simultaneously. The chemical structures, optical and electrochemical properties of three AzIn-based PHAs have been investigated, as well as their protonation behaviors with trifluoroacetic acid (TFA). All three AzIn-based PHAs exhibit narrow optical band gaps with moderate to good air stability, anti-Kasha emission and reversible stimuli-responsiveness. Furthermore, these straightforward and simple synthetic routes would provide a new entry for constructing novel azulene-embedded π-conjugates, especially for the seven-membered ring of azulene unit, wherein the regioselective transformation is not well developed. |
| |
| Keywords: | azulene Cadogan reaction polycyclic heteroaromatics protonation synthetic methods |
|
|
