一锅法手性富勒烯 C76 的对映选择性萃取，使用带有非对称扭曲的、高π碱性卟啉模块的环状主体。

One-pot enantioselective extraction of chiral fullerene C76 using a cyclic host carrying an asymmetrically distorted, highly pi-basic porphyrin module.

机构信息

Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.

出版信息

J Am Chem Soc. 2010 May 5;132(17):5928-9. doi: 10.1021/ja910701q.

DOI:10.1021/ja910701q

PMID:20373806

Abstract

Optical resolution of nonsubstituted chiral fullerenes such as C(76) is one of the most challenging subjects in host-guest chemistry. The novel cyclic host 1(2H), which bears a meso-diaryl-beta-octaethylporphyrin (P(2H)) unit on one side and its chiral N-2-acetoxyethyl derivative (P(N-EtOAc)) on the other, traps C(76) enantioselectively in its cavity and furnishes 7% enantiomeric excess in a single extraction. Control experiments using reference hosts indicated the importance of the high pi-basicity and large asymmetric distortion of the chiral N-substituted porphyrin unit (P(N-EtOAc)) in 1(2H) for the enantioselection of C(76).

摘要

非取代手性富勒烯（如 C(76)）的对映体拆分是主客体化学中最具挑战性的课题之一。新型环状主体 1(2H) 一侧带有一个间二芳基-β-辛基乙基卟啉（P(2H)）单元，另一侧带有其手性 N-2-乙氧基乙酰基衍生物（P(N-EtOAc))，可在其空腔中选择性地捕获 C(76)，并在单次萃取中提供 7%的对映体过量。使用参考主体进行的对照实验表明，手性 N-取代卟啉单元（P(N-EtOAc)) 的高 π-碱性和大不对称扭曲对 1(2H) 中 C(76) 的对映体选择的重要性。