Trefoil-Shaped Porous Nanographenes Bearing a Tribenzotriquinacene Core by Three-fold Scholl Macrocyclization

Angewandte Chemie
Lisi HeHak-Fun Chow

Abstract

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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Citations

Jul 26, 2019·Angewandte Chemie·Marek GrzybowskiDaniel T Gryko
Feb 15, 2020·Chemical Science·Rafal ZuzakDiego Peña
Apr 8, 2021·The Journal of Organic Chemistry·Ho-Wang IpHak-Fun Chow
Dec 10, 2020·Journal of the American Chemical Society·Zhen ShanGen Zhang
Jan 29, 2020·The Journal of Organic Chemistry·Philippe WagnerMichael Mastalerz
Oct 6, 2018·Journal of the American Chemical Society·Hanna GregolińskaMarcin Stępień
Aug 28, 2021·Chemistry : a European Journal·Chihiro MaedaTadashi Ema

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