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

被引：22

作者：

Lederle, Felix ^{[1
]}

Meyer, Frederick ^{[1
]}

Kaldun, Christian ^{[1
]}

Namyslo, Jan C. ^{[1
]}

Huebner, Eike G. ^{[1
]}

机构：

[1] Tech Univ Clausthal, Inst Organ Chem, Leibnizstr 6, D-38678 Clausthal Zellerfeld, Germany

来源：

NEW JOURNAL OF CHEMISTRY | 2017年 / 41卷 / 05期

关键词：

NONLINEAR-OPTICAL-PROPERTIES; STATE DIPOLE-MOMENTS; ONE-POT SYNTHESIS; COPPER-FREE; CHEMICAL-SYNTHESIS; SOLVATOCHROMIC METHOD; ORGANIC-MOLECULES; ARYL BROMIDES; TRIPLE BOND; REACTIONWARE;

D O I：

10.1039/c6nj03614g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：1925 / 1932

页数：8

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