- 著者
- Shigehiro Yamaguchi Aiko Fukazawa Masayasu Taki
- 出版者
- The Society of Synthetic Organic Chemistry, Japan
- 雑誌
- Journal of Synthetic Organic Chemistry, Japan (ISSN:00379980)
- 巻号頁・発行日
- vol.75, no.11, pp.1179-1187, 2017-11-01 (Released:2017-11-09)
- 参考文献数
- 94
- 被引用文献数
- 14
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.
- 著者
- Atsushi Wakamiya Shigehiro Yamaguchi
- 出版者
- (社)日本化学会
- 雑誌
- Bulletin of the Chemical Society of Japan (ISSN:00092673)
- 巻号頁・発行日
- vol.88, no.10, pp.1357-1377, 2015-10-15 (Released:2015-10-15)
- 参考文献数
- 179
- 被引用文献数
- 218
Boron, a group 13 element, has several characteristic structural and electronic features: 1) trivalent boron compounds usually adopt a trigonal planar geometry; 2) due to the presence of a vacant p-orbital, effective orbital interaction with π-conjugated compounds is possible; 3) the presence of a vacant p-orbital is furthermore responsible for high Lewis acidity; 4) the boryl group acts as a π-electron-accepting group particularly in the excited state. The consequent exploitation of these characteristic features of boron in the molecular design enables us to produce sophisticated π-functional materials with attractive photophysical and electronic properties. This account article illustrates our systematic studies on the molecular design and the development of functional π-electron materials using boron as a key element.