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Trefoil‐Shaped Porous Nanographenes Bearing a Tribenzotriquinacene Core by Three‐fold Scholl Macrocyclization
Author(s) -
He Lisi,
Ng ChunFai,
Li Yuke,
Liu Zhifeng,
Kuck Dietmar,
Chow HakFun
Publication year - 2018
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.201808461
Subject(s) - chemistry , stacking , crystallography , intramolecular force , spectroscopy , nuclear magnetic resonance spectroscopy , hexa , ion , yield (engineering) , stereochemistry , materials science , organic chemistry , physics , metallurgy , quantum mechanics
Porous curved polycyclic aromatic compounds 6 and 14 bearing a tribenzotriquinacene (TBTQ) core encircled by an m,p,p,m,m,p,p,m,m,p,p,m ‐cyclododecaphenylene belt were synthesized and characterized by NMR spectroscopy and mass spectrometry. These trefoil hydrocarbon macrocycles were constructed in high yield using an intramolecular three‐fold Scholl macrocyclization. X‐ray crystal analysis of 14 demonstrated a large wizard‐hat‐shaped structure with three pores (radii 2.9–3.0 Å). The π‐stacking aggregation of the hexa‐ n ‐dodecyloxy derivative 6 a and the chloride anion binding properties of 14 were studied by NMR spectroscopy. Such stacking and anion binding properties were much weaker in the singly 11 and doubly macrocyclized products 12 .
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