Synthesis and spectroscopy of benzylamine-substituted BODIPYs for bioimaging Ripoll, Consuelo Cheng, Cheng García-Fernández, Emilio Li, Jin Orte Gutiérrez, Ángel Do, Hainam Jiao, Lijuan Robinson, David Crovetto González, Luis Gonzalez-Vera, Juan A. Talavera Rodríguez, Eva María Álvarez Pez, José María Boens, Noël Ruedas Rama, María José This is the peer reviewed version of the following article: Eur. J. Org. Chem. 2018, 2561–2571, which has been published in final form at https://doi.org/10.1002/ejoc.201800083. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. Three new boron dipyrromethene (BODIPY) dyes substituted with a benzylamino group at the 3-position have been synthesized from halogenated BODIPYs by nucleophilic substitution. The spectroscopic and photophysical properties have been explored in different solvents and have been compared with an analogous 8benzylaminoBODIPY derivative. The position of the benzylamino group has a significant influence on the spectral band positions, fluorescence quantum yields, and fluorescence lifetimes. The 8benzylaminoBODIPY emits in the blue range, whereas the 3substituted shows green fluorescence. Additionally, the extension of the conjugation at the 5-position of 3-benzylaminoBODIPY produces a bathochromic shift of the absorption and emission spectra. The solvent effect on their spectroscopic features has been investigated using the generalized Catalán solvent scales. Quantum-chemical calculations have been performed to assess the effect of the position of the substitution on the spectroscopic properties. Finally, the BODIPY dyes have been employed as probes in fluorescence lifetime imaging of living cells, demonstrating their high potential for bioimaging. 2019-03-11T07:07:31Z 2019-03-11T07:07:31Z 2018 info:eu-repo/semantics/article Ripoll, Consuelo... [et al.]. Synthesis and spectroscopy of benzylamine-substituted BODIPYs for bioimaging. Eur. J. Org. Chem. 2018, 2561–2571 https://doi.org/10.1002/ejoc.201800083 http://hdl.handle.net/10481/54913 10.1002/ejoc.201800083 eng info:eu-repo/semantics/openAccess Wiley-VCH