6533b824fe1ef96bd1281443

RESEARCH PRODUCT

Single Heteroatom Fine-Tuning of the Emissive Properties in Organoboron Complexes with 7-(Azaheteroaryl)indole Systems

Carmen Ramírez De ArellanoMaría F. MontenegroDavid CurielAlberto TárragaArturo Espinosa FeraoMiriam Más-montoyaJosé Neptuno Rodríguez-lópezLaura Usea

subject

Organic electronicsIndole test010405 organic chemistryOrganic ChemistryHeteroatomchemistry.chemical_elementElectronic structureFour-coordinate boron complexFluorophoreConjugated system010402 general chemistryBioimaging01 natural sciencesCombinatorial chemistry0104 chemical scienceschemistryOrganic chemistryEmission spectrumCyclic voltammetryBoron

description

The application of organoboron compounds as light-absorbing or light-emitting species in areas as relevant as organic electronics or biomedicine has motivated the search for new materials which contribute to the progress of those applications. This article reports the synthesis of four-coordinate boron complexes based on the unexplored 7-(azaheteroaryl)indole ligands. An easy synthetic approach has enabled the fine-tuning of the electronic structure of the organoboron species by modifying a heteroaromatic component in the conjugated system. Furthermore, a comprehensive characterization by X-ray diffraction, absorption and emission spectroscopy, both in solution and in the solid state, cyclic voltammetry, and computational methods has evidenced the utility of this simple strategy. Large Stokes shifts have been achieved in solid thin-films which show a range of emitted light from blue to orange. The synthesized compounds have been used as biocompatible fluorophores in cell bioimaging.

https://doi.org/10.1021/acs.joc.6b00265