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

9 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

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Alkynes
alkynes
esters
dimers
synthesis
rhodium
Dimers
Esters
Aromatization
fluorescence
Rhodium
electrons
Fluorescence
Electrons
8-cycloparaphenylene

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization. / Hayase, Norihiko; Miyauchi, Yuta; Aida, Yukimasa; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken.

In: Organic Letters, Vol. 19, No. 11, 02.06.2017, p. 2993-2996.

Research output: Contribution to journalArticle

Hayase, Norihiko ; Miyauchi, Yuta ; Aida, Yukimasa ; Sugiyama, Haruki ; Uekusa, Hidehiro ; Shibata, Yu ; Tanaka, Ken. / Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization. In: Organic Letters. 2017 ; Vol. 19, No. 11. pp. 2993-2996.
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