A porphyrin-based gelator assembly which is reinforced by peripheral urea groups and chirally twisted by chiral urea additives

Shun Ichi Tamaru, Shin Ya Uchino, Masayuki Takeuchi, Masato Ikeda, Tsukasa Hatano, Seiji Shinkai

研究成果: Contribution to journalArticle

63 被引用数 (Scopus)

抄録

A novel porphyrin (1b) bearing four urea groups at its periphery was synthesized. This compound tends to aggregate into one-dimensional direction, resulting in an organogel phase in anisole and diphenyl ether solvents. The gel can be formed even at 0.125 wt/vol% in anisole and the sol-gel phase transition temperatures (Tgel) are as high as 120-140°C, indicating that 1b acts as an excellent gelator for these specific solvents. The spectroscopic studies and electron-micrographic observations support the view that the π-π stacking interaction among porphyrin moieties and the hydrogen-bonding interaction among urea moieties operate synergistically to give rise to a stable one-dimensional aggregate structure indispensable for gel formation. Further interestingly, chiral urea derivatives are bound to this aggregate to twist it in a chiral manner. This is a unique example for a rationally-designed organogelator including a porphyrin core and urea peripheral groups.

本文言語英語
ページ(範囲)3751-3755
ページ数5
ジャーナルTetrahedron Letters
43
20
DOI
出版ステータス出版済み - 5 13 2002

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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