FULL PAPER Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures Marisol Ibarra‐Rodríguez 1 | Blanca M. Muñoz‐Flores 1 | Alberto Gómez‐Treviño 1 | Rodrigo Chan‐Navarro 1 | Jessica C. Berrones‐Reyes 1 | Arturo Chávez‐Reyes 2 | H.V. Rasika Dias 3 | Mario Sánchez Vázquez 4 | Víctor M. Jiménez‐Pérez 1 1 Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Ciudad Universitaria, 66451Nuevo León, Mexico 2 Centro de Investigación y de Estudios Avanzados del IPN, Unidad Monterrey, PIIT, C.P, 66600 Apodaca, Nuevo León, Mexico 3 Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019‐0065, USA 4 Centro de Investigación en Materiales Avanzados, S.C., Alianza Norte 202, PIIT, Carretera Monterrey‐Aeropuerto Km. 10, C. P, 66628 Apodaca, Nuevo León, Mexico Correspondence Víctor M. Jiménez‐Pérez, Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Ciudad Universitaria, 66451 Nuevo León, Mexico. Email: victor.jimenezpr@uanl.edu.mx Funding information Consejo Nacional de Ciencia y Tecnología (CONACYT), Grant/Award Number: 240011; Robert A. Welch Foundation, Grant/Award Number: Y‐1289 The fluorescence imaging technologies are becoming the most powerful and noninvasive diagnostic tools in cellular biology and modern medicine where abnormal cell arrangements are associated with diseases. Thus, these tech- niques require new fluorescent dyes with excellent chemical, physical, and photophysical properties. A series of four new Boron Schiff bases (1–4) has been prepared by condensation between phenylboronic acid with the corre- sponding ligand. The compounds were characterized by NMR ( 1 H, 13 C, and 11 B), UV/vis, fluorescence spectroscopy, and high‐resolution mass spectrome- try. The crystal structures of three compounds showed tetracoordinated Boron atoms with semiplanar skeleton ligands. Interesting organoboron response to viscosity on their fluorescence (Φ: more than 3‐fold). Additionally, compounds 1 and 2 were found to serve as a fluorescent dye for cell imaging (B16F10, CaCo, and A‐431 cells) since it has the capability to rapidly accumulate within the cells and gave bright green fluorescence, it showed low cytotoxicity activity and high photostability in solution. Additionally, the compounds have also been investigated using DFT. KEYWORDS bioimaging, BOSCHIBAs, high photostability, low cytotoxicity 1 | INTRODUCTION In the recent decade, fluorescent organoboron compounds have gained tremendous attention due to different and interesting applications such as optoelectronic devices, [1] sensors, [2,3] security inks, [4,5] and fluorescent bioimaging (FBI). [6,7] The cellular biology and biomedicine are quite interesting about the advances in fluorescence imaging technologies to identify organelle and cellular abnormalities which are associated with severe diseases and disabilities. [8] It is important to know the anatomy and physiology in the cellular structure and organelles (e.g., mitochondria, the endoplasmic reticulum, lyso- somes, Golgi apparatus, and vacuoles). In particular, the cytoplasm is the solution where are suspended some major the organelles and provides mechanical support to Received: 7 September 2018 Revised: 11 October 2018 Accepted: 28 October 2018 DOI: 10.1002/aoc.4718 Appl Organometal Chem. 2019;e4718. https://doi.org/10.1002/aoc.4718 © 2019 John Wiley & Sons, Ltd. wileyonlinelibrary.com/journal/aoc 1 of 11