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Effective Binding of Neutral Dinitriles by Pillar[4]arene[1]quinone both in Solution and in Solid State
Author(s) -
Han Chengyou,
Zhao Dezhi,
Li Haiyu,
Wang Haibo,
Huang Xu,
Sun Daofeng
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702793
Subject(s) - quinone , pillar , chemistry , chloroform , molecule , nuclear magnetic resonance spectroscopy , succinonitrile , crystallography , solid state , stereochemistry , calixarene , organic chemistry , structural engineering , electrode , engineering , electrolyte
Herein two kinds of pillar[5]arene derivatives, DMpillar[4]arene[1]quinone and DPpillar[4]arene[1]quinone were synthesized. Their host−guest complexation properties were explored and we found that neutral dinitriles can thread through the cavity of pillar[4]arene[1]quinones to form [2]pseudorotaxanes in chloroform, which were confirmed by 1 H NMR spectroscopy. Of all the guests, the succinonitrile showed the most effective binding affinity with the host molecules in this work. Strikingly, X‐ray single‐crystal analysis between DMpillar[4]arene[1]quinone and 1,4‐dicyanobutane indicates the formation of the threaded structure.