1258278-93-1Relevant articles and documents
Copper-Catalyzed N,N-Diarylation of Amides for the Construction of 9,10-Dihydroacridine Structure and Applications in the Synthesis of Diverse Nitrogen-Embedded Polyacenes
Tan, Mei-Ling,Tong, Shuo,Hou, Sheng-Kai,You, Jingsong,Wang, Mei-Xiang
supporting information, p. 5417 - 5422 (2020/07/08)
We reported herein CuI/DMEDA catalyzed N,N-diarylation reaction of amides with various di(o-bromoaryl)methanes to produce diverse 9,10-dihydroacridine derivatives. The resulting 9,10-dihydroacridine derivatives were oxidized selectively under mild conditions to afford acridine, acridinone, and acridinium derivatives. The copper-catalyzed N,N-diarylation reaction coupled with oxidative aromatization reaction enabled the facile construction of nitrogen atom-embedded tetracenes and pentacenes of different ortho-fused patterns. The luminescence properties, especially the effect of fusion pattern on fluorescence emission of acquired N-polycenes, were also demonstrated.
Synthesis and comparative characterization of 9-boraanthracene, 5-boranaphthacene, and 6-borapentacene stabilized by the H2IMes carbene
Wood, Thomas K.,Piers, Warren E.,Keay, Brian A.,Parvez, Masood
supporting information; experimental part, p. 12199 - 12206 (2011/02/25)
A general procedure for the preparation of three N-heterocyclic carbene stabilized, boron-containing acenes (9-boraanthracene, 5-boranaphthacene, and 6-borapentacene) is presented. The key steps involve a transmetallation reaction between BCl3 and an appropriate stannacyclic precursor, and the dehydrochlorination of the H2IMes adduct of the chloroborane product. Comparative structural, photophysical, and redox properties reveal narrow HOMO-LUMO gaps relative to the all-carbon acene analogues. Just add boron: Synthetic routes to the N-heterocyclic-carbene-stabilized 5-boranaphthacene and 6-borapentacene are described and complement that previously developed for 9-boraanthracene. Comparative structural, photophysical, and redox properties reveal narrow HOMO-LUMO gaps relative to the all-carbon acene analogues.