TY - JOUR
T1 - Solvent-Induced Sign Inversion of Circularly Polarized Luminescence
T2 - Control of Excimer Chirality by Hydrogen Bonding
AU - Takaishi, Kazuto
AU - Iwachido, Kazuhiro
AU - Ema, Tadashi
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant JP17K05786, the Mitsui Chemicals, Inc. Award in Synthetic Organic Chemistry, Japan, the JGC-Scholarship Foundation, and the Wesco Scientific Promotion Foundation.
Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/1/29
Y1 - 2020/1/29
N2 - A series of pyrenes sandwiched by axially chiral 1,1′-binaphthyls were synthesized. Among them, (R,R)-3 possessing 2-hydroxy-3,3′-dimethylbinaphthyls exhibited solvent-dependent inversion of the sign of circularly polarized luminescence (CPL) without a change in emission wavelength. The (-)- and (+)-CPL were detected in nonpolar and polar solvents, respectively, with glum values of -0.012 and +0.012. This switching property originates from the inversion of excimer chirality caused by the presence or absence of intermolecular hydrogen bonds in the excited state. The CPL intensity was also changed by variation of the temperature and concentration.
AB - A series of pyrenes sandwiched by axially chiral 1,1′-binaphthyls were synthesized. Among them, (R,R)-3 possessing 2-hydroxy-3,3′-dimethylbinaphthyls exhibited solvent-dependent inversion of the sign of circularly polarized luminescence (CPL) without a change in emission wavelength. The (-)- and (+)-CPL were detected in nonpolar and polar solvents, respectively, with glum values of -0.012 and +0.012. This switching property originates from the inversion of excimer chirality caused by the presence or absence of intermolecular hydrogen bonds in the excited state. The CPL intensity was also changed by variation of the temperature and concentration.
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U2 - 10.1021/jacs.9b13184
DO - 10.1021/jacs.9b13184
M3 - Article
C2 - 31909994
AN - SCOPUS:85078335026
SN - 0002-7863
VL - 142
SP - 1774
EP - 1779
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 4
ER -