10.1021/acs.joc.6b00265.s001 Miriam Más-Montoya Miriam Más-Montoya Laura Usea Laura Usea Arturo Espinosa Ferao Arturo Espinosa Ferao María F. Montenegro María F. Montenegro Carmen Ramírez de Arellano Carmen Ramírez de Arellano Alberto Tárraga Alberto Tárraga José N. Rodríguez-López José N. Rodríguez-López David Curiel David Curiel Single Heteroatom Fine-Tuning of the Emissive Properties in Organoboron Complexes with 7‑(Azaheteroaryl)indole Systems American Chemical Society 2016 article reports characterization Large Stokes shifts Azaheteroaryl heteroaromatic component electronic Emissive Properties biomedicine ligand absorption azaheteroaryl strategy Heteroatom application complex Organoboron Complexes cell bioimaging progress utility approach organoboron species material organoboron compounds emission spectroscopy cyclic voltammetry diffraction solution biocompatible fluorophores method synthesis 2016-03-18 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Single_Heteroatom_Fine_Tuning_of_the_Emissive_Properties_in_Organoboron_Complexes_with_7_Azaheteroaryl_indole_Systems/3126301 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.