Systematic investigations on fused π-system compounds of seven benzene rings prepared by photocyclization of diphenanthrylethenes

Shota Fujino, Minoru Yamaji, Hideki Okamoto, Toshiki Mutai, Isao Yoshikawa, Hirohiko Houjou, Fumito Tani

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

We studied the photoproducts of 1-(n-phenanthryl)-2-(m-phenanthryl)ethenes (nEm; n, m = 1, 3 and 9) for understanding photocyclization patterns based on NMR spectroscopy. The crystal structures of the photoproducts were analyzed by X-ray crystallography, and the photophysical features of the photocyclized molecules were investigated based on emission and transient absorption measurements. Phenanthrene derivatives substituted at the 1- and 3-positions were prepared for synthesizing nEm by photocyclization of stilbene derivatives. We obtained four types of primary photoproducts (n@m) from the corresponding nEm. Two of them were found to have racemic molecular structures in the single crystal determined by X-ray crystallography. Besides the primary photoproducts, two types of secondary photoproducts (n@mPP) were isolated. Fluorescence quantum yields and lifetimes of the obtained photoproducts were determined in solution whereas the definite fluorescence quantum yields were obtained in the powder. Observation of the triplet-triplet absorption spectra in solution by laser photolysis techniques showed that intersystem crossing to the triplet state competes with the fluorescence process.

Original languageEnglish
Pages (from-to)925-934
Number of pages10
JournalPhotochemical and Photobiological Sciences
Volume16
Issue number6
DOIs
Publication statusPublished - 2017

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Benzene
Fluorescence
X ray crystallography
benzene
Quantum yield
fluorescence
crystallography
rings
Derivatives
Stilbenes
phenanthrene
stilbene
Photolysis
Powders
Molecular structure
Nuclear magnetic resonance spectroscopy
atomic energy levels
photolysis
Absorption spectra
x rays

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Systematic investigations on fused π-system compounds of seven benzene rings prepared by photocyclization of diphenanthrylethenes. / Fujino, Shota; Yamaji, Minoru; Okamoto, Hideki; Mutai, Toshiki; Yoshikawa, Isao; Houjou, Hirohiko; Tani, Fumito.

In: Photochemical and Photobiological Sciences, Vol. 16, No. 6, 2017, p. 925-934.

Research output: Contribution to journalArticle

Fujino, Shota ; Yamaji, Minoru ; Okamoto, Hideki ; Mutai, Toshiki ; Yoshikawa, Isao ; Houjou, Hirohiko ; Tani, Fumito. / Systematic investigations on fused π-system compounds of seven benzene rings prepared by photocyclization of diphenanthrylethenes. In: Photochemical and Photobiological Sciences. 2017 ; Vol. 16, No. 6. pp. 925-934.
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AU - Yoshikawa, Isao

AU - Houjou, Hirohiko

AU - Tani, Fumito

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