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Issue 5, 2017
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Sonogashira coupling in 3D-printed NMR cuvettes: synthesis and properties of arylnaphthylalkynes

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Abstract

3D-Printing has been used to build hollow NMR tube/spinner combinations out of NMR-transparent polyamide. The whole 3D-print has been processed inside a glove box and during pauses of the 3D-printing process, all reactants for the palladium-catalyzed decarboxylative Sonogashira coupling of aryl halides with arylpropiolic acids have been inserted. Within the totally gas tight and pressure resistant tubes, a set of arylnaphthylalkynes has been synthesized and the progress of the reaction has been monitored via NMR spectroscopy. The (nonlinear) optical properties of the push–pull substituted bis(aryl)alkynes have been investigated by fluorescence spectroscopy and DFT calculations. A significant correlation between the intensity of the triple-bond stretching vibration and the calculated first hyperpolarizability is reported.

Graphical abstract: Sonogashira coupling in 3D-printed NMR cuvettes: synthesis and properties of arylnaphthylalkynes

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Supplementary files

Article information


Submitted
18 Nov 2016
Accepted
26 Jan 2017
First published
02 Feb 2017

New J. Chem., 2017,41, 1925-1932
Article type
Paper

Sonogashira coupling in 3D-printed NMR cuvettes: synthesis and properties of arylnaphthylalkynes

F. Lederle, F. Meyer, C. Kaldun, J. C. Namyslo and E. G. Hübner, New J. Chem., 2017, 41, 1925
DOI: 10.1039/C6NJ03614G

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