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Issue 2, 2017
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Selective synthesis of iridium(III)-derived molecular Borromean rings, [2]catenane and ring-in-ring macrocycles via coordination-driven self-assembly

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Abstract

This paper reports the formation of unprecedented iridium(III)-derived topological macrocycles. Discrete molecular Borromean rings 1 and 3 in pure form are synthesized via coordination-driven self-assembly of an acceptor [(Cp*Ir)2(OO∩OO)](OTf)2 (Cp* = pentamethylcyclopentadienyl, OO∩OO = 6,11-dioxido-5,12-naphthacenedione) (A) with dipyridyl donors 1,4-bis(4-pyridinylethynyl)benzene (L1) and 2,5-bis(4-pyridinylethynyl)thiophene (L2) respectively in methanol. Self-assembly using the same acceptor under similar conditions with two other donors 9,10-bis(4-pyridinylethynyl)anthracene (L3) and 1,4-di(4-pyridinylethynyl)buta-1,3-diyne (L4) resulted in [2]catenane 5 and non-catenane ring-in-ring topological macrocycle 7 respectively. Rectangular macrocycles 2, 4, 6, and 8 were respectively obtained when the self-assembly of acceptor A with one of the donors L1–L4 was carried out under dilute conditions in nitromethane or methanol. All these new macrocycles were characterized by 1H and 13C NMR, 2D NMR, ESI-MS and elemental analyses. Single crystal X-ray structures of Borromean rings 1 and 3, and ring-in-ring macrocycle 7 revealed that the length and functionality of donors enabling CH⋯π and π⋯π interactions govern the topology.

Graphical abstract: Selective synthesis of iridium(iii)-derived molecular Borromean rings, [2]catenane and ring-in-ring macrocycles via coordination-driven self-assembly

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Publication details

The article was received on 29 Nov 2016, accepted on 07 Dec 2016 and first published on 07 Dec 2016


Article type: Paper
DOI: 10.1039/C6DT04512J
Citation: Dalton Trans., 2017,46, 571-577
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    Selective synthesis of iridium(III)-derived molecular Borromean rings, [2]catenane and ring-in-ring macrocycles via coordination-driven self-assembly

    N. Singh, D. Kim, D. H. Kim, E. Kim, H. Kim, M. S. Lah and K. Chi, Dalton Trans., 2017, 46, 571
    DOI: 10.1039/C6DT04512J

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