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https://doi.org/10.1002/anie.202002447
Title: | Benzidine/Quinoidal-Benzidine Linked, Superbenzene Based π-Conjugated Chiral Macrocycles and Cyclophanes | Authors: | LI GUANGWU Matsuno, T. Han, Y. PHAN VAN HOA 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. https://doi.org/10.1002/anie.202002447 | 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 | URI: | https://scholarbank.nus.edu.sg/handle/10635/167848 | ISSN: | 1433-7851 | DOI: | 10.1002/anie.202002447 |
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