4.5 Article

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

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JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 852, 期 -, 页码 64-73

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ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2017.10.003

关键词

BOSCHIBAs; Cytoplasm staining; Low cytotoxicity; High photostability; Fluorescent bioimaging

资金

  1. CONACYT [240011]
  2. PAICYT-UANL [CE336-15]

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In 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 (H-1, C-13, and B-11), FT-IR, and atmospheric pressure ionization time-of-flight mass spectrometry. BOSCHIBA1a was 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. BOSCHIBAs 1a-3a and their ligands 1-3 exhibit relatively low quantum yields in a range from 1 to 3%. In a bioimaging study by using the BOSCHIBAs 2a, and 3a as fluorescent staining dyes, those materials showed enhanced features in terms of low cytotoxicity, simple synthesis, photostability, hydrolytic stability and specific staining for cytoplasm structures. (C) 2017 Published by Elsevier B.V.

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