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Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids

Using 2-hydroxypropyl-protecting groups, 1,8-dialkynylanthracene photo-dimers were prepared in head-to-head-configuration by UV irradiation on a multi-gram scale. In non-polar solvents, the combination of non-covalent hydrogen bonds and π–π-interactions induces the formation of the syn-isomer in up...

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Autores principales: Niermeier, Philipp, Maibom, Kristina A. M., Lamm, Jan-Hendrik, Neumann, Beate, Stammler, Hans-Georg, Mitzel, Norbert W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8230024/
https://www.ncbi.nlm.nih.gov/pubmed/34257857
http://dx.doi.org/10.1039/d1sc02065j
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author Niermeier, Philipp
Maibom, Kristina A. M.
Lamm, Jan-Hendrik
Neumann, Beate
Stammler, Hans-Georg
Mitzel, Norbert W.
author_facet Niermeier, Philipp
Maibom, Kristina A. M.
Lamm, Jan-Hendrik
Neumann, Beate
Stammler, Hans-Georg
Mitzel, Norbert W.
author_sort Niermeier, Philipp
collection PubMed
description Using 2-hydroxypropyl-protecting groups, 1,8-dialkynylanthracene photo-dimers were prepared in head-to-head-configuration by UV irradiation on a multi-gram scale. In non-polar solvents, the combination of non-covalent hydrogen bonds and π–π-interactions induces the formation of the syn-isomer in up to 85% yield. Instead, more polar solvents or irradiation of unprotected 1,8-diethynylanthracene led to formation of the corresponding anti-isomer in large excess. Cleavage of the protecting groups under basic conditions affords a rigid hydrocarbon skeleton with four directional functions. This was used as a building block for a tetradentate boron Lewis acid. Its applicability as a host for Lewis-base substrates was demonstrated by the formation of adducts with various nitrogen bases. Adduct formation with hydrazine leads to impressive networks between the tetraboron host and the substrate molecules.
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spelling pubmed-82300242021-07-12 Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids Niermeier, Philipp Maibom, Kristina A. M. Lamm, Jan-Hendrik Neumann, Beate Stammler, Hans-Georg Mitzel, Norbert W. Chem Sci Chemistry Using 2-hydroxypropyl-protecting groups, 1,8-dialkynylanthracene photo-dimers were prepared in head-to-head-configuration by UV irradiation on a multi-gram scale. In non-polar solvents, the combination of non-covalent hydrogen bonds and π–π-interactions induces the formation of the syn-isomer in up to 85% yield. Instead, more polar solvents or irradiation of unprotected 1,8-diethynylanthracene led to formation of the corresponding anti-isomer in large excess. Cleavage of the protecting groups under basic conditions affords a rigid hydrocarbon skeleton with four directional functions. This was used as a building block for a tetradentate boron Lewis acid. Its applicability as a host for Lewis-base substrates was demonstrated by the formation of adducts with various nitrogen bases. Adduct formation with hydrazine leads to impressive networks between the tetraboron host and the substrate molecules. The Royal Society of Chemistry 2021-05-06 /pmc/articles/PMC8230024/ /pubmed/34257857 http://dx.doi.org/10.1039/d1sc02065j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Niermeier, Philipp
Maibom, Kristina A. M.
Lamm, Jan-Hendrik
Neumann, Beate
Stammler, Hans-Georg
Mitzel, Norbert W.
Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids
title Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids
title_full Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids
title_fullStr Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids
title_full_unstemmed Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids
title_short Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate Lewis acids
title_sort hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene – access to tetradentate lewis acids
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8230024/
https://www.ncbi.nlm.nih.gov/pubmed/34257857
http://dx.doi.org/10.1039/d1sc02065j
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