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Updated: Feb 10, 2026
Synthesis and Characterization of Functionalized Metal-organic Frameworks
Published on: September 5, 2014
Synthesis, Characterization, and Functionalization of 1-Boraphenalenes
Rachel J Kahan1, Daniel L Crossley1, Jessica Cid1
1School of Chemistry, University of Manchester, Manchester, M13 9PL, UK.
Abstract:
1-Boraphenalenes have been synthesized by reaction of BBr3 with 1-(aryl-ethynyl)naphthalenes, 1-ethynylnaphthalene, and 1-(pent-1-yn-1-yl)naphthalene and they can be selectively functionalized at boron or carbon to form bench-stable products. All of these 1-boraphenalenes have LUMOs localized on the planar C12 B core that are closely comparable in character to isoelectronic phenalenyl cations. In contrast to the comparable LUMOs, the aromatic stabilization of the C5 B ring in 1-boraphenalenes is dramatically lower than the C6 rings in phenalenyl cations. This is due to the occupied orbitals of π symmetry being less delocalised in the 1-boraphenalenes.
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