Fluorescent Modular Boron Systems Based on NNN- and ONO-Tridentate Ligands: Self-Assembly and Cell Imaging

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• 作者：Christoph Glotzbach ; Ulrike Kauscher ; Jens Voskuhl ; N. Seda Kehr ; Marc C. A. Stuart ; Roland Fr枚hlich ; Hans J. Galla ; Bart Jan Ravoo ; Kazuhiko Nagura ; Shohei Saito ; Shigehiro Yamaguchi ; Ernst-Ulrich W眉rthwein
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：May 3, 2013
• 年：2013
• 卷：78
• 期：9
• 页码：4410-4418
• 全文大小：486K
• 年卷期：v.78,no.9(May 3, 2013)
• ISSN：1520-6904

文摘

We have synthesized a series of new fluorescent boron systems 1a鈥?b>c and 2a鈥?b>d based on nitrogen (NNN) or nitrogen and oxygen (ONO)-containing tridentate ligands. These novel dyes are characterized by high thermal and chemical stability. They show large Stokes shifts (mostly above 3200 cm^鈥?) and quantum yields in solution and in the solid state up to 40%. The easy, modular synthesis facilitates the convenient variation of the axial substituent on the central boron atom, allowing the functionalization of this dye for biochemical use. Introducing a long alkyl chain with a phenyl spacer at this axial position enables the self-assembly of the boron compound 2d to form a fluorescent vesicle, which is able to encapsulate small molecules such as sulforhodamine. Additionally, boron compound 2d was found to serve as a dye for cell imaging since it has the capability of binding to the nuclear membranes of HeLa cells. With phospholipids such as DOPC, giant unilamelar vesicles (GUV) are formed. These results demonstrate the wide applicability of this new boron system in supramolecular and medicinal chemistry.