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Angew Chem Int Ed Engl. 2019 Feb 11;58(7):1965-1969. doi: 10.1002/anie.201812696. Epub 2019 Jan 24.

Bidentate Boron Lewis Acids: Selectivity in Host-Guest Complex Formation.

Author information

1
Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2, Fakultät für Chemie, Universität Bielefeld, Universitätsstraße 25, 33615, Bielefeld, Germany.

Abstract

Bidentate boron Lewis acids based on 1,8-diethynylanthracene were synthesised in two steps by initial stannylation of the terminal alkynes and subsequent tin-boron exchange with different chloroboranes. The reactions were very selective, and the target compounds were obtained in high purity and good to excellent yields. Complexation experiments of 1,8-bis[(diphenylboranyl)ethynyl]anthracene with nitrogen bases (pyridine, pyrimidine, TMEDA) afforded three stable adducts, which were structurally characterised by X-ray diffraction. Competition experiments demonstrated the selective exchange of guests, and quantum-chemical calculations provided information on their energetics. NMR experiments at low temperature gave insight into the dynamic behaviour of the TMEDA adduct.

KEYWORDS:

1,8-diethynylanthracene; host-guest complexes; molecular recognition; poly-Lewis acids; tin-boron exchange

PMID:
30576056
DOI:
10.1002/anie.201812696

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