Synthesis of substituted picenes through Pd-catalyzed cross-coupling reaction/annulation sequences and their physicochemical properties

Ning Hui Chang, Xi Chao Chen, Hikaru Nonobe, Yasuhiro Okuda, Hiroki Mori, Kiyohiko Nakajima, Yasushi Nishihara

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A novel and versatile synthetic method for picene derivatives is developed using the Pd-catalyzed intramolecular double cyclization of the corresponding 2,3-bis[(1Z)-2-phenylethenyl]-1,4-dichlorobenzenes, which are readily prepared by Suzuki-Miyaura cross-coupling reactions of polyhalobenzenes with (Z)-arylethenylboronates. The physical properties of the obtained picenes can be modified via introducing a variety of functional groups to the picene framework. All compounds are investigated by UV-vis and fluorescence spectroscopic measurements, CV, and DFT calculations as well as X-ray diffraction analysis.

Original languageEnglish
Pages (from-to)3558-3561
Number of pages4
JournalOrganic Letters
Volume15
Issue number14
DOIs
Publication statusPublished - Jul 19 2013

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cross coupling
Cross Reactions
physical properties
fluorescence
Cyclization
synthesis
diffraction
Discrete Fourier transforms
X-Ray Diffraction
X ray diffraction analysis
Functional groups
x rays
Physical properties
Fluorescence
Derivatives
picene
4-dichlorobenzene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis of substituted picenes through Pd-catalyzed cross-coupling reaction/annulation sequences and their physicochemical properties. / Chang, Ning Hui; Chen, Xi Chao; Nonobe, Hikaru; Okuda, Yasuhiro; Mori, Hiroki; Nakajima, Kiyohiko; Nishihara, Yasushi.

In: Organic Letters, Vol. 15, No. 14, 19.07.2013, p. 3558-3561.

Research output: Contribution to journalArticle

Chang, Ning Hui ; Chen, Xi Chao ; Nonobe, Hikaru ; Okuda, Yasuhiro ; Mori, Hiroki ; Nakajima, Kiyohiko ; Nishihara, Yasushi. / Synthesis of substituted picenes through Pd-catalyzed cross-coupling reaction/annulation sequences and their physicochemical properties. In: Organic Letters. 2013 ; Vol. 15, No. 14. pp. 3558-3561.
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