Neo-N-confused Phlorins and Phlorinone: Rational Synthesis and Tunable Properties

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• 作者：Jiahui Kong ; Jiewei Shao ; Chengjie Li ; Dongdong Qi ; Minzhi Li ; Xu Liang ; Weihua Zhu ; Jianzhuang Jiang ; Yongshu Xie
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：650-653
• 全文大小：378K
• ISSN：1523-7052

文摘

By the acid-catalyzed [2 + 2] condensation, an unprecedented neo-N-confused phlorin (neo-NCphlorin 1) was successfully synthesized. By treating 1 with N-chlorosuccinimide, the corresponding chloro-substituted neo-NCphlorin (1-Cl) was obtained. The oxidization of 1 with FeCl₃ afforded the neo-N-confused phlorinone (neo-NCphlorinone 2), which bears a relatively coplanar conformation, different from the highly distorted ones observed for 1 and 1-Cl. Notably, 2 shows striking long-wavelength absorption beyond 1300 nm upon addition of TBAF.