Macrocycle contraction and expansion of a dihydrosapphyrin isomer

Yongshu Xie, Pingchun Wei, Xin Li, Tao Hong, Kai Zhang, Hiroyuki Furuta

Research output: Contribution to journalArticle

115 Citations (Scopus)

Abstract

Cyclization of a pentapyrrane with two terminal β-linked pyrroles afforded a dihydrosapphyrin isomer (1) with the pyrroles linked in a unique β,α-α,β mode, which was rather reactive, and thus it readily underwent a ring-contracted rearrangement to a pyrrolyl norrole (2), and succeeding ring expansion to a terpyrrole-containing isosmaragdyrin analogue (4). 1, 2, and 4 contain the internal ring pathways with a minimum of 17, 15, and 16 atoms, respectively. 1, 2, and 4 are almost nonfluorescent, whereas the complex of 2 with Zn2+ shows a distinct NIR emission peak at 741 nm. The unprecedented pyrrole transformation chemistry by confusion approach is illustrated.

Original languageEnglish
Pages (from-to)19119-19122
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number51
DOIs
Publication statusPublished - Dec 26 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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