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

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posted on 18.03.2016 by Miriam Más-Montoya, Laura Usea, Arturo Espinosa Ferao, María F. Montenegro, Carmen Ramírez de Arellano, Alberto Tárraga, José N. Rodríguez-López, David Curiel
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.