Synlett 2022; 33(02): 161-165
DOI: 10.1055/a-1470-6050
letter
EuCheMS Organic Division Young Investigator Workshop

Highly Fluorinated Trianglimine Macrocycles: A Supramolecular Organic Framework

Tom Kunde
a   Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany
,
Tobias Pausch
a   Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany
,
Guido J. Reiss
b   Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany
,
a   Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany
› Author Affiliations
This work was supported by the Fonds der Chemischen Industrie by a Kekulé Fellowship (T.K.), by the North Rhine-Westphalian Academy of Sciences, Humanities and the Arts (B.M.S.), and the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) (SCHM 3101/5-1).


Abstract

A novel highly fluorinated dialdehyde was prepared by a two-stage synthesis. This reactive building block for dynamic imine chemistry was used in a condensation reaction to generate the first extensively fluorinated trianglimine. An analysis of the material properties and, especially, the crystal structure of the [3+3] macrocycle revealed a supramolecular organic framework with tubular porous channels. The use of fluorinated ligands to generate hydrophobic electron-deficient channel-like pores is an important addition to the ever-expanding field of supramolecular networks and to trianglimine chemistry in general.

Supporting Information



Publication History

Received: 18 March 2021

Accepted after revision: 30 March 2021

Accepted Manuscript online:
30 March 2021

Article published online:
20 April 2021

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