期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 19, 页码 13252-13264出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01113
关键词
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资金
- Czech Science Foundation [17-02578S]
- project Strategy AV21 (Efficient energy conversion and storage)
- project e-Infrastruktura CZ within the program Projects of Large Research, Development, and Innovation Infrastructures [e-INFRA LM2018140]
A novel methodology for the successful synthesis of aza[n]-phenacenes was developed, introducing nitrogen atoms to induce changes in physicochemical properties. The important characteristics of the prepared aza[n]phenacenes were studied experimentally and compared to their carbo analogues. Features of the crystalline aza[n]phenacenes were also investigated, including intermolecular interactions and changes in solubility or melting points.
A novel methodology for the synthesis of aza[n]-phenacenes was successfully developed utilizing photocyclodehydro-chlorination reaction of 2-chloro-N-aryl-1-naphthamides. In these key intermediates, the factors influencing the photoreaction were studied. The target aza[n]phenacenes were obtained by triflation or chlorination from prepared phenanthridinones, followed by hydrogenation. The introduction of a nitrogen atom into a phenacene skeleton induced changes in the physicochemical properties. The important properties of prepared aza[n]phenacenes (n = 4-6) were studied experimentally and by density functional theory calculations and were compared to those of their carbo analogues. Furthermore, some important features of the crystalline aza[n]phenacenes were investigated, including intermolecular interaction in the crystal lattice and the increased solubility or decreased melting points.
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