Synthesis and Characterization of Oxadisilole-Fused 9-Aminoacridines and 12-Aminobenzo[b]acridines

Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at room temperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical,...

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Veröffentlicht in:European journal of organic chemistry 2014-07, Vol.2014 (19), p.4170-4178
Hauptverfasser: Chen, Xuanming, Zhang, Yajuan, Chen, Yali, Zhang, Jie, Chen, Jingda, Li, Minjie, Cao, Weiguo, Chen, Jie
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Sprache:eng
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Zusammenfassung:Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at room temperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined. The oxadisilole‐fused 9‐aminoacridines show potential for use as blue emitters for OLED applications, because of their high fluorescence quantum yields and good thermal stabilities. The proposed mechanism was also studied. Theoretical calculations on the HOMO and LUMO values of these compounds were performned. Oxadisilole‐fused 9‐aminoacridines and 12‐aminobenzo[b]acridines have been synthesized by the nucleophilic addition and 1,5‐hydrogen shift reaction of arynes with 2‐aminobenzonitriles in good yield at roomtemperature. Dioxatrisilole‐fused 9‐aminoacridines have also been obtained. The photophysical, redox, and thermal properties of these compounds have been determined.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402361