Synthesis, Properties, and Reactivity of Bis-BN Phenanthrenes: Stepwise Bromination of the Main Scaffold

Lingjian Zi; Jinyun Zhang; Chenglong Li; Yi Qu; Bin Zhen; Xuguang Liu; Lei Zhang

doi:10.1021/acs.orglett.0c00021

Synthesis, Properties, and Reactivity of Bis-BN Phenanthrenes: Stepwise Bromination of the Main Scaffold

Org Lett. 2020 Feb 21;22(4):1499-1503. doi: 10.1021/acs.orglett.0c00021. Epub 2020 Feb 10.

Authors

Lingjian Zi¹, Jinyun Zhang¹, Chenglong Li¹, Yi Qu¹, Bin Zhen¹, Xuguang Liu^{1

2}, Lei Zhang³

Affiliations

¹ Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, Tianjin Key Laboratory of Drug Targeting and Bioimaging, School of Chemistry and Chemical Engineering , Tianjin University of Technology , Tianjin 300384 , People's Republic of China.
² Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , People's Republic of China.
³ School of Science , Tianjin Chengjian University , Tianjin 300384 , People's Republic of China.

PMID: 32037843
DOI: 10.1021/acs.orglett.0c00021

Abstract

Two bis-BN phenanthrenes have been synthesized. Their photophysical properties are different from those of the reported mono-BN phenanthrenes. Moreover, the stepwise bromination of bis-BN phenanthrene 8 gave a series of brominated bis-BN phenanthrenes, with all of the mono-, di-, tri-, and tetrabrominated bis-BN phenanthrenes being successfully isolated and characterized. In addition, preliminary results showed that mono- and dibrominated species can be further functionalized by cross-coupling reactions.