TY - JOUR
T1 - Circular Polarized Luminescence of Hydrogen-Bonded Molecular Assemblies of Chiral Pyrene Derivatives
AU - Anetai, Hayato
AU - Takeda, Takashi
AU - Hoshino, Norihisa
AU - Araki, Yasuyuki
AU - Wada, Takehiko
AU - Yamamoto, Shunsuke
AU - Mitsuishi, Masaya
AU - Tsuchida, Hiromu
AU - Ogoshi, Tomoki
AU - Akutagawa, Tomoyuki
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “π-Figuration” (JP26102007), KAKENHI Kibankenkyu (B) (JP15H03791), JSPS Research Fellow (16J03265), and “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” from MEXT.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/3/22
Y1 - 2018/3/22
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.jpcc.7b12747
DO - 10.1021/acs.jpcc.7b12747
M3 - Article
AN - SCOPUS:85044378983
VL - 122
SP - 6323
EP - 6331
JO - Journal of Physical Chemistry C
JF - Journal of Physical Chemistry C
SN - 1932-7447
IS - 11
ER -