Azaborine chemistry and applications

In recent years, there has been an enormous interest in azaborine, aromatic compounds in which a C=C bond has been replaced by the isoelectric B-N bond. In this way, new compounds can be accessed that retain aromaticity but present very different properties due to the polarization of the B-N bond.
In this context, we have started a line aimed at developing new synthetic routes for the preparation of BN-isosters of polycyclic aromatic compounds, focusing on the search for simple and efficient methods and the possibility of accessing structures not described so far. On the other hand, the analysis of the physical-chemical properties of the synthesized compounds allows the acquisition of new knowledge about the behavior of these systems, with the final objective of facilitating the rational design of more complex systems with improved properties, mainly from a photophysical point of view.

Recent publications:

Hyper-Cross-Linked Porous Polymer Featuring B-N Covalent Bonds (HCP-BNs): A Stable and Efficient Metal-Free Heterogeneous Photocatalyst.
ACS Macro Lett. 2023, 12(7):949-954. doi: 10.1021/acsmacrolett.3c00217. Epub 2023 Jun 29.
β-Functionalization of 4 a-aza-8 a-boranaphthalene via Iridium-catalyzed C−H Borylation.
Advanced Synthesis & Catalysis. 2023; n/a(n/a).
Synthesis of Five-Membered Organoborate Heterocycles via a Metal-Free Carboboration and Their Use in Cross-Coupling Reactions.
2023; (EFirst).
Synthesis of BN-Polyarenes by a Mild Borylative Cyclization Cascade.
Org Lett. 2022;24(31):5860-5865. doi: 10.1021/acs.orglett.2c02477.
1,10a-Dihydro-1-aza-10a-boraphenanthrene and 6a,7-Dihydro-7-aza-6a-boratetraphene: Two New Fluorescent BN-PAHs.
J. Org. Chem. 2021, 86, 23, 16259
Recent developments in the chemistry of BN-aromatic hydrocarbons.
Adv. Heterocycl. Chem. 2021, 197
Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene.
Chem Commun 2020, 56, 3669
A New Member of the BN-Phenanthrene Family: Understanding the Role of the B-N Bond Position.
J Org Chem. 2019, 84, 7113
Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene.
Beilstein J. Org. Chem. 2019, 15, 1257
Synthesis, Functionalization, and Optical Properties of 1,2-Dihydro-1-aza-2-boraphenanthrene and Several Highly Fluorescent Derivatives.
Org Lett. 2019, 21, 2550
C-H Functionalization of BN-Aromatics Promoted by Addition of Organolithium Compounds to the Boron Atom.
Org Lett. 2018, 20, 4902
Synthesis of functionalized helical BN-benzo%c%phenanthrenes.
Chem Commun 2018, 54, 2467
Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene.
Org Lett. 2017, 19, 3458