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

Abstract

A set of push–pull substituted arylnaphthylalkynes has been synthesized under inert gas conditions in 3D-printed cuvettes out of NMR-transparent polyamide and their optical properties were investigated.

3D printing for chemical, pharmaceutical and biological applications

“…Inside this gas tight and pressure resistant reaction vessel a series of arylnapthylalkynes were synthesised, with the reaction progress being monitored via NMR spectroscopy. 19 Other demonstrations of printed analytical hardware have included ultraviolet-visible (UV-Vis) spectroscopy, 20 light emitting diode array detection, 21 flow cytometry, 22 magnetic resonance imaging, 23 scanning electron microscopy, 24 polymerase chain reaction, 25 low temperature plasma ionization, 26 electrophoresis, 27 and direct spray ionization mass spectrometry. 28 8…”

Increasing the functionalities of 3D printed microchemical devices by single material, multimaterial, and print-pause-print 3D printing

“…Within the totally gas tight and pressure resistant tubes, a set of arylnaphthylalkynes was synthesized and the progress of the reaction was monitored via NMR spectroscopy. 57…”

Additive Manufacturing Technologies: 3D Printing in Organic Synthesis

“…In 2017 Hübner and co‐workers used 3D printing approach to build gastight NMR tube/spinner combination and cuvettes for studying the Sonogashira coupling between aryl halides and arylpropiolic acids by magnetic resonance and infrared spectroscopy …”

“…In 2017 Hübner and co-workersu sed 3D printing approach to build gastightN MR tube/spinner combination and cuvettes for studying the Sonogashira coupling between aryl halides and arylpropiolic acids by magnetic resonance and infrared spectroscopy. [43] Ar eaction flask wasf abricated from polyamide (Taulman 910), compatible with the most common organic solvents and completely invisible in NMR spectroscopy.T he printing process was performed in an inert gas atmosphere (glove box) and the reagents were filled inside the reactor during some pauses of [41] Scheme8.A) CAD Designed photoreactor.B)3D-printed and assembled photoreactor.R eproduced with permission from Ananikov et al [42] ChemCatChem 2018, 10,1512 -1525 www.chemcatchem.org the printing( Scheme 9). In this study the authors werea ble to correlate the donor capability of different aryl bromidest ot he reactionr ate, and the opticalp roperties of isolated bis-arylalkynes were investigated by fluorescence spectroscopy and DFT calculations.…”