2020年6月15日
Spiro-Conjugated Carbon/Heteroatom-Bridgedp-Phenylenevinylenes: Synthesis, Properties, and Microcrystal Electron Crystallographic Analysis of Racemic Solid Solutions
Bulletin of the Chemical Society of Japan
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- 巻
- 93
- 号
- 6
- 開始ページ
- 776
- 終了ページ
- 782
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1246/bcsj.20200065
- 出版者・発行元
- The Chemical Society of Japan
Two planar conjugated systems perpendicularly connected via a quaternary sp(3) carbon center interact with each other through the spiro linkage. Such spiro-conjugated pi-systems show useful optoelectronic properties. Herein, we present a unified modular synthetic strategy for a series of chiral spiroconjugated carbocycles utilizing a C-H activation reaction as a key step. The chiral spiro-conjugated carbon/heteroatombridged p-phenylenevinylenes (spiro-X compounds) possessing C, O, N, S, and SO2 as bridging groups are thermally stable, and exhibit circular dichroism and circularly polarized luminescence (CPL). Spiro-SO2 undergoes intramolecular charge transfer. It exhibits CPL with a large vertical bar g(lum)vertical bar of 2.1 x 10(-3) and shows rarely reported solvatofluorochromism for CPL luminophores. The racemic spiro-O compound solidifies as a racemic solid solution (or pseudoracemate). It did not form X-ray-quality crystals. This therefore provided us with a unique opportunity to examine the potential of the microcrystal electron crystallography popularized recently. The diffraction data sets, merged over many micrometer-sized solid particles, afforded the 3D molecular structure and the crystal packing of the spiro compound.
- リンク情報
- ID情報
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- DOI : 10.1246/bcsj.20200065
- ISSN : 0009-2673
- ISSN : 1348-0634
- eISSN : 1348-0634
- ORCIDのPut Code : 99487015
- Web of Science ID : WOS:000540717800008