杯[3]咔唑：一步合成与主客体结合

Calix[3]carbazole: One-Step Synthesis and Host-Guest Binding.

作者信息

Yang Peng, Jian Yong, Zhou Xue, Li Gang, Deng Tuo, Shen Hongyan, Yang Zhaozheng, Tian Zhangmin

机构信息

Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University , Shenyang 110016, People's Republic of China.

出版信息

J Org Chem. 2016 Apr 1;81(7):2974-80. doi: 10.1021/acs.joc.6b00252. Epub 2016 Mar 21.

DOI:10.1021/acs.joc.6b00252

PMID:26967021

Abstract

The one-step synthetic strategy for the preparation of the hitherto unknown calix[3]carbazole from readily available starting materials is described. Calix[3]carbazole is obtained in 20% yield, and it could selectively bind the N(C2H5)4(+) cation (tetraethylammonium, TEA) via cation-π interactions. The experimental and modeling results indicate that calix[3]carbazole possesses a larger π-cavity as well as a better chromophoric property than the traditional phenol-based macrocycles, and thus is capable of binding to and optically responding to the relatively large guest TEA.

摘要

本文描述了一种由易得的起始原料一步合成迄今未知的杯[3]咔唑的策略。杯[3]咔唑的产率为20%，它可通过阳离子-π相互作用选择性地结合N(C2H5)4(+)阳离子（四乙铵，TEA）。实验和建模结果表明，杯[3]咔唑比传统的基于苯酚的大环化合物具有更大的π-腔以及更好的发色性能，因此能够结合相对较大的客体TEA并对其产生光学响应。