Synthesis, characterization, photophysical properties of new fluorescent boron Schiff bases (BOSCHIBAs) and their application as cytoplasm staining dyes in?vitro

摘要

AbstractIn this paper, we report a series of Schiff bases synthesized by the condensation reaction between 2-hydroxy-1-naphthaldehyde with aniline derivatives as well as their further coordination with diphenylborinic acid for giving the corresponding boron Schiff bases (BOSCHIBAs) (E)-N-((2-((di-phenylboryl)oxy)naphthalen-1-yl)methylene)pyridin-3-amine (1a), (E)-N-((2-((di-phenylboryl)oxy)naphthalen-1-yl)methylene)-2,6-di-methylaniline (2a), and (E)-N-((2-((di-phenylboryl)oxy)naphthalen-1-yl)methylene)-2,6-di-isopropylaniline (3a). The resulting BOSCHIBAs were characterized by NMR (1H,13C, and11B), FT-IR, and atmospheric pressure ionization time-of-flight mass spectrometry. BOSCHIBA1awas structurally characterized by single-crystal. Structure analysis indicates that the boron atom adopts a tetrahedral molecular geometry into a six-membered ring with a half-chair conformation. BOSCHIBAs1a-3aand their ligands1-3exhibit relatively low quantum yields in a range from 1 to 3%. In a bioimaging study by using the BOSCHIBAs2a, and3aas fluorescent staining dyes, those materials showed enhanced features in terms of low cytotoxicity, simple synthesis, photostability, hydrolytic stability and specific staining for cytoplasm structures.展开▼