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Issue 6, 2014
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Perfluorinated 1H-indazoles and hydrotris(indazol-1-yl)borates. Supramolecular organization and a new synthetic procedure to form scorpionate ligands

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Abstract

This paper describes the syntheses and full characterization of perfluorinated 1H-indazoles 2–5 and hydrotris(indazolyl)borate thallium complexes 6–9 that contain linear perfluoroalkyl chains varying from two to six carbon atoms in the 3-position. In the solid state, the perfluorinated 1H-indazoles exhibit supramolecular structures that depend on the length of the perfluoroalkyl chain. A catemer of order 3 is observed for the CF2CF3 derivative 2 (chiral space group P32), catemers of order 2 are observed for the C3F7 and C4F9 derivatives 3 (chiral space group P212121, one type of helix in the unit cell) and 4 (space group P21/n, two types of helices in the unit cell), respectively, and stacks of dimers are observed for the indazole with the longer C6F13 chain 5 (space group P21/c). The perfluorinated hydrotris(indazolyl)borate thallium complexes 6–9 [TlFn–Tp4Bo,3Rf] have been obtained by a new reaction based on the reaction of HBBr2 (generated in situ from BBr3 and Et3SiH) with the indazolates of 2–5 followed by cation exchange. The X-ray crystal structure of [TlF33–Tp4Bo,3C3F7] 7 shows that, in addition to coordination to the three nitrogens, the thallium is buried in a nest of fluorines with seven short intramolecular Tl⋯F contacts with the pendant perfluoropropyl chains. The potential of these highly fluorinated molecules to act as ligands is highlighted.

Graphical abstract: Perfluorinated 1H-indazoles and hydrotris(indazol-1-yl)borates. Supramolecular organization and a new synthetic procedure to form scorpionate ligands

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Publication details

The article was received on 27 Jan 2014, accepted on 26 Feb 2014 and first published on 18 Mar 2014


Article type: Paper
DOI: 10.1039/C4NJ00136B
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Citation: New J. Chem., 2014,38, 2451-2461
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    Perfluorinated 1H-indazoles and hydrotris(indazol-1-yl)borates. Supramolecular organization and a new synthetic procedure to form scorpionate ligands

    B. K. Muñoz, W. Ojo, K. Jacob, N. Romero, L. Vendier, E. Despagnet-Ayoub and M. Etienne, New J. Chem., 2014, 38, 2451
    DOI: 10.1039/C4NJ00136B

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