ortho-Phenylene-Bridged Cyclic Oligopyrroles: Conformational Flexibilities and Optical Properties

Fengkun Chen, Takayuki Tanaka, Yongseok Hong, Woojae Kim, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

ortho-Phenylene-bridged cyclic trimeric oligopyrrole C3 and hexameric oligopyrrole C6 were synthesized by Suzuki–Miyaura coupling reactions. The twisted structures of C3 and C6 were unambiguously revealed by X-ray diffraction analysis. The optical properties of these cyclic oligopyrroles were compared with linear oligopyrrole L3 and cyclic tetramer C4. The cyclic oligopyrroles exhibited large Stokes shifts and blue fluorescence with high quantum yields in solution and in the solid state. In addition, selective N-methylation and N-tolylation of C3 were used to tune the optical and electrochemical properties by changing the molecular twists and conformational flexibilities. Throughout these studies, the structure–property relationship of these cyclic strained oligopyrroles has been illustrated as an interesting molecular motif for novel cyclic π-conjugated systems.

Original languageEnglish
Pages (from-to)10597-10606
Number of pages10
JournalChemistry - A European Journal
Volume22
Issue number30
DOIs
Publication statusPublished - 2016 Jul 18

Bibliographical note

Funding Information:
The work at Kyoto was supported by JSPS (KAKENHI grant numbers 25220802 and 26810021). The work at Yonsei was supported by the Global Research Laboratory (GRL) Program funded by the Ministry of Science, ICT and Future, Korea (2013K1A1A2A02050183).

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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