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Acyclic Janus‐AT Nucleoside Host Channels Precisely Lock Water into Single‐File Wires with Local Rotational Flexibility
Author(s) -
Zhou Xinglong,
Shen Zhen,
Ma Beibei,
Xia Zhenqiang,
Chai Yingying,
Ju Xiaojie,
Chu Liangyin,
Huang Ridong,
Chen Hai,
Li Weimin,
He Yang
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904204
Subject(s) - intermolecular force , hydrogen bond , janus , molecule , chemistry , chemical physics , crystallography , stacking , stereochemistry , materials science , nanotechnology , organic chemistry
Confining polar water molecules to particular geometries demands sophisticated intermolecular interactions, and not many small synthetic molecules have accomplished such a task. Herein, regioisomeric acyclic Janus‐AT nucleosides ( 1 and 2 ), with a self‐complementary fused genetic alphabet and conformationally flexible side chains, have been selectively synthesized. 1 and 2 adopt disparate base‐pair motifs from the π–π stacked hydrophobic base moieties and distinct hydrogen bond (HB) interconnections from the hydrophilic sugar residues, which in turn lead to divergent, intricate intermolecular interaction networks with different capacities to confine water molecules. Under the precise control of the host framework of the N 8 ‐regioisomer, separate ordered single‐file water wires can be locked through special three‐HB clamps into unique inter‐ and intra‐wire geometrical alignments. Localized dynamic synchronized rotations within the fixed framework coordinated by both the host hydroxy groups and guest water molecules were observed in a temperature‐induced reversible single‐crystal‐to‐single‐crystal transition (SCSCT).