Rhodium-Catalyzed Synthesis, Crystal Structures, and Photophysical Properties of [6]Cycloparaphenylene Tetracarboxylates

Norihiko Hayase, Haruki Sugiyama, Hidehiro Uekusa, Yu Shibata, Ken Tanaka

Research output: Contribution to journalArticle

Abstract

The synthesis of C 2 -symmetrical [6]cycloparaphenylene (CPP) tetracarboxylates has been achieved via macrocyclization by the rhodium-catalyzed intermolecular stepwise cross-alkyne cyclotrimerization and subsequent reductive aromatization. The 1 H NMR spectra of the thus-obtained C 2 -symmetrical [6]CPP-tetracarboxylates revealed that the rotation of unsubstituted benzene rings is slow at room temperature. These [6]CPPs formed columnar packing structures, and their absorption maxima were significantly blue-shifted compared to that of nonsubstituted [6]CPP due to the presence of four electron-withdrawing ester moieties.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

Fingerprint

Aromatization
Rhodium
Alkynes
alkynes
Benzene
rhodium
esters
Esters
Crystal structure
benzene
Nuclear magnetic resonance
Electrons
nuclear magnetic resonance
crystal structure
Temperature
rings
room temperature
synthesis
electrons
3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rhodium-Catalyzed Synthesis, Crystal Structures, and Photophysical Properties of [6]Cycloparaphenylene Tetracarboxylates. / Hayase, Norihiko; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken.

In: Organic Letters, 01.01.2019.

Research output: Contribution to journalArticle

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