Synthesis, Structure, and Photophysical/Chiroptical Properties of Benzopicene-Based π-Conjugated Molecules

Koichi Murayama, Yu Shibata, Haruki Sugiyama, Hidehiro Uekusa, Ken Tanaka

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The convenient synthesis of substituted benzopicenes and azabenzopicenes has been achieved by the cationic rhodium(I)/H8-BINAP or BINAP complex-catalyzed [2+2+2] cycloaddition under mild conditions. This method was applied to the synthesis of benzopicene-based long ladder and helical molecules. The X-ray crystal structure analysis revealed that the benzopicene-based helical molecule is highly distorted and the average distance of overlapped rings is markedly shorter than that in the triphenylene-based helical molecule. Photophysical and chiroptical properties of these benzopicene and azabenzopicene derivatives have also been examined. With respect to photophysical properties, substituted benzopicenes and azabenzopicenes showed red shifts of absorption and emission maxima compared with the corresponding triphenylenes and azatriphenylenes. With respect to chiroptical properties, the CPL spectra of the benzopicene-based helical molecule showed two opposite peaks, and thus the value of the CPL was smaller than that of the triphenylene-based helical molecule presumably due to the presence of two chiral fluorophores.

Original languageEnglish
Pages (from-to)1136-1144
Number of pages9
JournalJournal of Organic Chemistry
Volume82
Issue number2
DOIs
Publication statusPublished - 2017 Jan 20
Externally publishedYes

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Molecules
Rhodium
Cycloaddition
Fluorophores
Ladders
Crystal structure
Derivatives
X rays
triphenylene
2-naphthol BINAP

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis, Structure, and Photophysical/Chiroptical Properties of Benzopicene-Based π-Conjugated Molecules. / Murayama, Koichi; Shibata, Yu; Sugiyama, Haruki; Uekusa, Hidehiro; Tanaka, Ken.

In: Journal of Organic Chemistry, Vol. 82, No. 2, 20.01.2017, p. 1136-1144.

Research output: Contribution to journalArticle

Murayama, Koichi ; Shibata, Yu ; Sugiyama, Haruki ; Uekusa, Hidehiro ; Tanaka, Ken. / Synthesis, Structure, and Photophysical/Chiroptical Properties of Benzopicene-Based π-Conjugated Molecules. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 2. pp. 1136-1144.
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