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Crystalline Naphthylene Macrocycles Capturing Gaseous Small Molecules in Chiral Nanopores
Author(s) -
Matsuno Taisuke,
Fukunaga Kengo,
Kobayashi Shuhei,
Sarkar Parantap,
Sato Sota,
Ikeda Takuji,
Isobe Hiroyuki
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202000876
Subject(s) - nanopore , molecule , nanoporous , crystallography , materials science , adsorption , solvent , nanotechnology , chemistry , organic chemistry
A series of chiral naphthylene macrocycles, [ n ]cyclo‐ epi ‐naphthylenes ([ n ]CeNAPs), possessing epi ‐linkages were synthesized by one‐pot macrocyclization. With chiral ( R )‐ or ( S )‐1,1′‐linkages embedded in binaphthyl precursors, the macrocycles were assembled in polygonal structures possessing chiral hinges as corners. Among four chiral [ n ]CeNAP variants, [8]CeNAP with eight naphthylene panels formed robust columnar assemblies in crystals. The nanoporous crystals maintained a columnar assembly structure even after the removal of encapsulated solvent molecules, and their gas adsorption behavior was thoroughly investigated. Gas adsorption, including state‐of‐the‐art in situ crystallographic analyses, revealed accurate atomic‐level structures of the nanopores trapping gaseous N 2 molecules in chiral C 2 arrangements. With macrocycles as basic frameworks, functional nanopores may be exploited for chiral small‐molecule alignments.