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Synthesis of a tethered dibenzotetramethyltetraaza[14]annulene macrocycle and the di-nickel(II) derivative

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Abstract

Selective reaction of 2,6-isophthaloyl chloride at the methine positions of two dibenzotetramethyltetraaza[14]annulene (tmtaa) units results in tethering of the macrocycles by either one or two 2,6-isophthaloyl bridging groups. The single tethered dibenzotetramethyltetraaza[14]annulene derivative (SIT-tmtaa) was isolated and characterized by X-ray crystallography, ESI-MS, 1H and 13C NMR. The syn conformation of the two tmtaa units observed in the crystal structure, has tetraaza[14]annulene macrocycles that are more distorted from planarity than in the structure of the parent tmtaa. The di-nickel(II) complex was prepared and characterized by ESI-HRMS, 1H and 13C NMR. DFT computations place the LUMO on the 2,6-isophthaloyl bridge rather than on the tethered tmtaa units and suggest that the 2,6-isophthaloyl tether provides a level of flexibility in the inter tmtaa distances that is comparable to the Pacman Effect observed for tethered porphyrins.

Graphical abstract: Synthesis of a tethered dibenzotetramethyltetraaza[14]annulene macrocycle and the di-nickel(ii) derivative

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Publication details

The article was received on 25 Jun 2018, accepted on 12 Sep 2018 and first published on 20 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ03154A
Citation: New J. Chem., 2018, Advance Article
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    Synthesis of a tethered dibenzotetramethyltetraaza[14]annulene macrocycle and the di-nickel(II) derivative

    S. Dey, J. R. Dewey, B. B. Wayland and M. J. Zdilla, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ03154A

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