Synthesis of chlorophyll–quinone conjugates by Diels-Alder reaction and their fluorescence quenching by intramolecular electron transfer
Dyes and Pigments(2024)
摘要
Methyl pyropheophorbides-a possessing a 1,4-naphthoquinon-5-yl or 9,10-anthraquinon-1-yl group at the 3-position were prepared by the Diels–Alder reaction of 3-(1,3-butadienyl)chlorin with benzoquinone or naphthoquinone and successive dehydrogenative oxidation. The synthetic chlorophyll-a derivatives directly bonded with the quinone were atropisomers around the C3–C31 bond, which were readily separated by HPLC. Since the quinone moiety was nearly perpendicular to the chlorin π-system, the distance and orientation between the chlorin and quinone chromophores were fixed in a molecule. The visible absorption spectra of the synthetic chlorin–quinone conjugates were independent of the quinone part and the axial chirality. Their fluorescence emissions were almost completely quenched by intramolecular electron transfer from the photoexcited chlorin to the quinone, which resembled the charge-separating process in photosynthetic reaction centers.
更多查看译文
AI 理解论文
溯源树
样例
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
生成溯源树,研究论文发展脉络
Chat Paper
正在生成论文摘要