Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization

Norihiko Hayase, Yuta Miyauchi, Yukimasa Aida, Haruki Sugiyama, Hidehiro Uekusa, Yu Shibata, Ken Tanaka

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The synthesis of C4- and C2-symmetrical [8]cycloparaphenylene (CPP)-octacarboxylates has been achieved via macrocyclization by the rhodium-catalyzed intermolecular stepwise cross-cyclotrimerization and subsequent reductive aromatization. The C4-symmetrical octa-tert-butyl [8]CPP-octacarboxylate forms a dimer in which eight ester moieties face each other. The dimers are aligned so as to make a one-dimensional column with a channel structure inside. Both absorption and fluorescence maxima of [8]CPP-octacarboxylates in CHCl3 were significantly blue-shifted compared to those of [8]CPP due to the presence of eight electron-withdrawing ester moieties.

Original languageEnglish
Pages (from-to)2993-2996
Number of pages4
JournalOrganic Letters
Volume19
Issue number11
DOIs
Publication statusPublished - 2017 Jun 2
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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