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. 2018 Mar 15;8:4590. doi: 10.1038/s41598-018-22892-8

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© The Author(s) 2018

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Chemical Mechanism of BODIPY-based library Stokes shift. (A) Compound BAA-16a did not have heteroatoms in its styryl extended π-system. The relatively long Stokes shift of 58 nm was attributed mainly to the bulky methyl substituents on the styryl extension of this fluorophore. (B) The resonance structures of BAA-39a and its molecular electrostatic potential surface are shown. The nitrogen in the pyrrolidine ring could share its lone pair electrons through the π-conjugated system, while the nitrogen in the pyridine ring could not. The negative charge (red) was localized between the boron and the fluorine atoms, while the positive charge (blue) was distributed along the π-conjugated system. (C) Correlation of the absolute value of the difference in dipole moments between the excited and ground states (|μ_es-μ_gs|) vs. the Stokes shift showed a linear relationship in the BAA library. The optimized geometries for the ground state (gs) and excited state (es) were obtained from DFT calculations using the B3LYP hybrid density functional with the 6–31 G(d,p) basis set.