期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 5, 页码 2176-2184出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo202212s
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资金
- Munster-Nagoya (Deutsche Forschungsgemeinschaft (DFG, Bad Godesberg)) [IRTG 1143]
- Fonds der Chemischen Industrie (Frankfurt)
- Grants-in-Aid for Scientific Research [19675001] Funding Source: KAKEN
Novel N-aryl-substituted 2-borylbenzaldimines 6 and related systems with extended pi-framework 7 based on two borylbenzaldimine units linked by a spacer moiety were synthesized by condensation reactions of 2-(dimesitylboryl)benzaldehyde 3 with various amines 4 and diamines 5. All compounds were completely characterized including X-ray diffraction, especially in view of Lewis acid-base B-O and B-N interactions. The electronic as well as the photophysical properties of bisimines 7 were determined using cyclic voltammetry, UV/vis, and fluorescence spectroscopy and quantum chemistry. These compounds feature large Stokes shifts and reversible reduction waves. Interestingly, UV irradiation experiments unfold enhanced photostability for compounds 7 with an extended pi-skeleton. By use of 1,8-diaminonaphthalene we observed the formation of a hitherto unknown BN-heterocyclic compound 9 fused with a perimidine skeleton. Structural and energetic aspects were evaluated by high level quantum chemical methods (DFT and SCS-MP2-calculations).
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