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説明:

Photosynthetic bacteria have evolved highly efficient light-harvesting systems by organizing chlorophyll (Chl) pigments into circular and tubular supramolecular arrays. To construct these surapmoelcular Chl arrays from the same molecular design, we synthesized two hydrogen-bonding chlorins using natural Chl-a as the starting material: free-base chlorin functionalized with hydrogen-bonding barbituric acid and second- or third-generation alkyl dendrons (G2 and G3, respectively). The barbituric acid moiety promotes the formation of a hydrogen-bonded cyclic hexamer known as rosette. In chloroform, both the synthetic Chl-a derivatives formed rosettes; however, in methylcyclohexane as a low-polarity solvent, the G2-dendron chlorin formed columnar structures by stacking rosettes, while the G3-dendron chlorin formed disc-shaped particles. AFM revealed the formation of extended helical fibers for the former and homogeneous nanoparticles, possibly single rosettes, for the latter. These results suggest that the third-generation of the dendron can inhibit the stacking of rosettes, leading to the formation of two distinct types of chlorin aggregates: circular and tubular.

権利情報:

• cc-by-3.0
  

キーワード: Supramolecular chemistry, Dendrimers, Atomic force microscopy, Transmission electron microscopy

刊行年月日: 2024-10-08

出版者: Royal Society of Chemistry (RSC)

掲載誌:

• Organic Chemistry Frontiers (ISSN: 20524129) vol. 11 issue. 22 p. 6304-6310

研究助成金:

• Japan Society for the Promotion of Science JP22H00331
• Japan Society for the Promotion of Science JP22H02203
• Japan Society for the Promotion of Science JP23H04874
• Japan Society for the Promotion of Science JP23H04873
• National Science Foundation DMR-0520547
• Horizon 2020 Framework Programme 654000

原稿種別: 出版者版 (Version of record)

MDR DOI:

公開URL: https://doi.org/10.1039/d4qo01629g

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更新時刻: 2024-11-06 16:30:30 +0900

MDRでの公開時刻: 2024-11-06 16:30:30 +0900