Phosphole P-Oxide-Containing π-Electron Materials: Synthesis and Applications in Fluorescence Imaging
Phosphole P-oxide is a useful building block for π-conjugated materials due to its nonaromatic and electron-accepting character. We have synthesized a series of ring-fused derivatives of phosphole P-oxide based on the intramolecular nucleophilic cyclization of appropriate alkyne precursors or radica...
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Veröffentlicht in: | Journal of Synthetic Organic Chemistry, Japan Japan, 2017/11/01, Vol.75(11), pp.1179-1187 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Phosphole P-oxide is a useful building block for π-conjugated materials due to its nonaromatic and electron-accepting character. We have synthesized a series of ring-fused derivatives of phosphole P-oxide based on the intramolecular nucleophilic cyclization of appropriate alkyne precursors or radical phosphanylations. Some of the thus obtained compounds exhibited intriguing fluorescence properties and were applied to fluorescence imaging. A donor-acceptor-type benzo[b]phosphole P-oxide with a (diphenylamino)phenyl group exhibited large solvatochromism in its fluorescence spectra, and could hence be used as a staining agent for lipid droplets. C-Naphox and PB430, which consist of fully ring-fused π-conjugated ladder-type scaffolds, exhibited outstanding photostability and their absorption and emission properties were suitable for super-resolution STED imaging. Moreover, using PB430-conjugated antibodies, we carried out a 3-D reconstruction of the STED images and developed a photostability-based multicolor STED imaging technique. |
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ISSN: | 0037-9980 1883-6526 |
DOI: | 10.5059/yukigoseikyokaishi.75.1179 |