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

作者：Kong, Jiahui; Shao, Jiewei; Li, Chengjie^*; Qi, Dongdong; Li, Minzhi; Liang, Xu; Zhu, Weihua; Jiang, Jianzhuang; Xie, Yongshu^*

来源：Organic Letters, 2017, 19(3): 650-653.

DOI：10.1021/acs.orglett.6b03816

• ANION-BINDING AGENTS
• EXPANDED PORPHYRINS
• ZN2+ PROBES
• CALIXPYRROLES
• CHEMISTRY
• CORROLE
• ISOMER
• MACROCYCLES
• RING
• CALIXPHYRINS

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.

• 出版日期2017-2-3
• 单位江苏大学; 华东理工大学; 北京科技大学