Song Zi-Hang, Ma Yi-Fan, Han Han, Li Dai-Yuan, Fu Rong, Zhao Qing-Yu, Wang Ruiguo, Guo Dong-Sheng, Cai Kang
College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin, 300071, China.
Department of Chemistry, The University of Hong Kong, Hong Kong SAR, 999077, China.
Chemistry. 2025 Jan 14;31(3):e202403271. doi: 10.1002/chem.202403271. Epub 2024 Dec 12.
While a plenty of macrocyclic hosts have been developed in supramolecular chemistry, those that combine chiral luminescent properties and host-guest recognition abilities are still uncommon. Herein, two pairs of enantiomeric macrocycles were synthesized via Suzuki-Miyaura [2+2] cyclization reactions using Tröger's base and diphenyl maleimide as the building blocks. The diphenyl maleimide units impart these macrocycles with highly strong fluorescence, achieving quantum yields up to 100 % in apolar solvents. Furthermore, the chiral, V-shaped Tröger's base units provide the macrocycles with circularly polarized luminescence (|g|=1.68×10) and well-define cavity for hosting electron-deficient or positively charged guests with K up to 1.7×10 M.
虽然超分子化学中已经开发了大量的大环主体，但那些结合了手性发光特性和主客体识别能力的主体仍然并不常见。在此，以特罗格碱和二苯基马来酰亚胺为构建单元，通过铃木-宫浦[2+2]环化反应合成了两对对映体大环。二苯基马来酰亚胺单元赋予这些大环非常强的荧光，在非极性溶剂中量子产率高达100%。此外，手性的V形特罗格碱单元为大环提供了圆偏振发光（|g|=1.68×10）以及明确的空腔，用于容纳缺电子或带正电荷的客体，结合常数高达1.7×10 M。
