Highly Twisted Fenestrindane-Based Porous Nanographenes.

Autor: Sun XQ; Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong., Li Y; Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong., Kuck D; Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, 33615, Bielefeld, Germany., Chow HF; Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Sep 07, pp. e202402931. Date of Electronic Publication: 2024 Sep 07.
DOI: 10.1002/chem.202402931
Abstrakt: Two fenestrindane-based porous nanographenes containing four polyaromatic macrocycles in a highly twisted, basically S 4 -symmetric conformation were synthesized and characterized by NMR spectroscopy and mass spectrometry. Stepwise π-extension at the periphery of the fenestrindane core by a sequence of eightfold Suzuki-Miyaura cross-coupling, fourfold Scholl cyclodehydrogenation and another eightfold Suzuki-Miyaura reaction affords the porous nanographene precursors in good yields. In the last step, fourfold intramolecular Yamamoto coupling generates the porous nanographenes in 17-18 %-yield. Their optical and electronic properties were studied by UV/Vis and fluorescence spectroscopy and cyclic voltammetry. DFT calculations revealed structural details of the macrocycles. The surprisingly weak binding of these porous structures with chloride ions (K≈10 M -1 ) is attributed to their highly twisted conformation. The title compounds represent the first porous nanographenes based on the [5.5.5.5]fenestrane motif and, at the same time, they consist of a fenestrane-like polyarylene network.
(© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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