Circular Polarized Luminescence of Hydrogen-Bonded Molecular Assemblies of Chiral Pyrene Derivatives

Hayato Anetai, Takashi Takeda, Norihisa Hoshino, Yasuyuki Araki, Takehiko Wada, Shunsuke Yamamoto, Masaya Mitsuishi, Hiromu Tsuchida, Tomoki Ogoshi, Tomoyuki Akutagawa

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45 Citations (Scopus)


The absorption and fluorescence spectra of chiral alkylamide-substituted pyrene derivatives (R-1 and S-1) in the solution phase were consistent with the formation of N-H···Oâ• hydrogen-bonded helical π-stacked one-dimensional (1D) supramolecules (R-1)n and (S-1)n in methylcyclohexane (MCH), toluene, chloroform (CHCl3), and tetrahydrofuran (THF); the π-stacked structures and aggregation number (n) were governed by the concentration (c) and solvent polarity. The aggregation of (R-1)n and (S-1)n in MCH and toluene was much greater than that in THF and CHCl3, and excimer emission of excited-state (R-1)n and (S-1)n supramolecules with n ≥ 2 was observed in all solvents. Interestingly, the circular polarized luminescence (CPL) spectra of (R-1)n and (S-1)n revealed a glum value of 0.03 in MCH at c > 1 × 10-6 M. Circular dichroism and CPL spectra revealed the formation of hydrogen-bonded helical 1D supramolecular assemblies in the ground and excited states. The helicities of the 1D supramolecular assemblies of (R-1)n and (S-1)n in CHCl3 were inverted as compared to those in MCH and THF. The solvent polarity and concentration were sensitive to the π-stacked structure and helical configuration of the N-H···Oâ• hydrogen-bonded 1D supramolecular assemblies.

Original languageEnglish
Pages (from-to)6323-6331
Number of pages9
JournalJournal of Physical Chemistry C
Issue number11
Publication statusPublished - 2018 Mar 22

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films


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