BN-arenes

Azaborine chemistry and applications

BN-arenes are isosteres of aromatic hydrocarbons in which a C=C bond is formally replaced by an isoelectronic B-N bond. Although these compounds preserve planarity and aromaticity, the intrinsic polarization introduced by the B–N linkage profoundly alters their electronic structure. As a result, BN-arenes often display enhanced and tunable photophysical properties relative to their all-carbon counterparts, making them highly attractive scaffolds for optoelectronic applications. In this context, we have developed a range of synthetic methodologies enabling access to previously unexplored BN-fused polycyclic architectures, along with strategies for their selective functionalization. We systematically investigate how structural modifications within these BN-polycycles influence their optical and electronic properties, establishing structure–property relationships that guide the design of next-generation functional materials.

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, 949
β-Functionalization of 4 a-aza-8 a-boranaphthalene via Iridium-catalyzed C−H Borylation.
Adv. Synth. Catal. 2023, 365, 2545
Synthesis of Five-Membered Organoborate Heterocycles via a Metal-Free Carboboration and Their Use in Cross-Coupling Reactions.
Synthesis 2023, 55, 1260
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 Nov 22. doi: 10.1021/acs.joc.1c01095.
Recent developments in the chemistry of BN-aromatic hydrocarbons.
Adv. Heterocycl. Chem. 2021 Mar 28; :197-259.
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

Biological Chemistry Group