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

被引：21
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
收藏
页码：1925 / 1932
页数：8
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