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Title: Benzidine/Quinoidal-Benzidine Linked, Superbenzene Based π-Conjugated Chiral Macrocycles and Cyclophanes
Authors: LI GUANGWU 
Matsuno, T.
Han, Y.
Wu, S
Jiang, Q.
Zou, Y.
Isobe, H.
Wu Jishan 
Issue Date: 18-Mar-2020
Publisher: Wiley-VCH
Citation: LI GUANGWU, Matsuno, T., Han, Y., PHAN VAN HOA, Wu, S, Jiang, Q., Zou, Y., Isobe, H., Wu Jishan (2020-03-18). Benzidine/Quinoidal-Benzidine Linked, Superbenzene Based π-Conjugated Chiral Macrocycles and Cyclophanes. Angewandte Chemie - International Edition. ScholarBank@NUS Repository.
Abstract: Synthesis of fully conjugated cyclophanes containing large-size polycyclic aromatics is challenging. Now, three benzidine-linked, hexa-peri-hexabenzocoronene (superbenzene)-based ortho-, para-, and meta-cyclophanes are synthesized through intermolecular Yamamoto coupling reaction of structurally pre-organized precursors. Subsequent oxidative dehydrogenation gave the corresponding quinoidal benzidine-linked cyclophanes. Their geometries were confirmed by X-ray crystallographic analysis and their electronic properties were investigated by electronic absorption, cyclic voltammetry, and DFT calculations. The quinoidal benzidine-linked cyclophanes show thermally populated paramagnetic activity with a relatively large singlet-triplet energy gap. Two enantiomers for the ortho-cyclophanes (1-NH and 1-N) were isolated and their chiral figure-of-eight macrocyclic structures were identified. The cage-like cyclophanes 2-NH and 3-NH with concave surface can selectively encapsulate fullerene C70.
Source Title: Angewandte Chemie - International Edition
ISSN: 1433-7851
DOI: 10.1002/anie.202002447
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