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Complexation of Racemic 2,6‐Helic[6]arene and Its Hexamethyl‐Substituted Derivative with Quaternary Ammonium Salts, N‐Heterocyclic Salts, and Tetracyanoquinodimethane
Author(s) -
Zhang GengWu,
Li PengFei,
Wang HanXiao,
Han Ying,
Chen ChuanFeng
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605394
Subject(s) - tetracyanoquinodimethane , chemistry , pyridinium , ammonium , derivative (finance) , salt (chemistry) , supramolecular chemistry , medicinal chemistry , organic chemistry , molecule , financial economics , economics
Complexation of racemic 2,6‐helic[6]arene 1 and its hexamethyl‐substituted derivative 2 with quaternary ammonium salts, N‐heterocyclic salts, and tetracyanoquinodimethane have been described in detail. It was found that host 2 could form stable complexes with acetyl choline, thiaacetyl choline, N , N , N ‐trimethylbenzenammonium salt, pyridinium, and 4,4′‐bipyridinium salts in solution and/or in the solid state. The unsubstituted macrocycle 1 showed more significant complexation with the widely tested quaternary ammonium salts and N‐heterocyclic salts, and exhibited stronger complexation towards the guests than its derivative 2 . Moreover, it was found that macrocycle 1 and its derivative 2 could also complex with neutral electron‐deficient tetracyanoquinodimethane (TCNQ), and the association constants were determined to be 2840±94 and 1358±46 m −1 , respectively. These results could make this new macrocycle and its derivatives find wide applications in the design and construction of functional supramolecular assemblies.