B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O₂ Sensitization

The judicial placement of main group elements in conjugated structures is emerging as a key route to novel functional hybrid materials. We demonstrate here that the formation of B–N Lewis pairs at the periphery of anthracene leads to buckling of the backbone while also dramatically lowering the LUMO energy. The resulting BN-substituted contorted polycyclic aromatic hydrocarbons show large bathochromic shifts in the absorption and emission relative to all-carbon analogs. In the presence of light, they rapidly react with O₂ without the need for an external photosensitizer, resulting in selective and reversible formation of the corresponding endoperoxides

B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O₂ Sensitization

The judicial placement of main group elements in conjugated structures is emerging as a key route to novel functional hybrid materials. We demonstrate here that the formation of B–N Lewis pairs at the periphery of anthracene leads to buckling of the backbone while also dramatically lowering the LUMO energy. The resulting BN-substituted contorted polycyclic aromatic hydrocarbons show large bathochromic shifts in the absorption and emission relative to all-carbon analogs. In the presence of light, they rapidly react with O₂ without the need for an external photosensitizer, resulting in selective and reversible formation of the corresponding endoperoxides

B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O₂ Sensitization

The judicial placement of main group elements in conjugated structures is emerging as a key route to novel functional hybrid materials. We demonstrate here that the formation of B–N Lewis pairs at the periphery of anthracene leads to buckling of the backbone while also dramatically lowering the LUMO energy. The resulting BN-substituted contorted polycyclic aromatic hydrocarbons show large bathochromic shifts in the absorption and emission relative to all-carbon analogs. In the presence of light, they rapidly react with O₂ without the need for an external photosensitizer, resulting in selective and reversible formation of the corresponding endoperoxides

Internal B ← O Bond Facilitated Photo/Thermal Isomerization of Tetra-Coordinated Boranes

A new series of O∧C-chelate tetra-coordinated boranes with naphtha-aldehyde as the chelate backbone have been synthesized. Their photophysical and photochemical properties have been examined, which show that all of the compounds can undergo both photo and thermal transformations, generating aryl-migrated [1,2]oxaborinine derivatives as the major products. 1,3-Sigmatropic shifts and an intramolecular nucleophilic addition mechanism are proposed for the photochemical and thermal conversion pathways, respectively