TY - JOUR
T1 - Ferroelectric Alkylamide-Substituted Helicene Derivative with Two-Dimensional Hydrogen-Bonding Lamellar Phase
AU - Anetai, Hayato
AU - Takeda, Takashi
AU - Hoshino, Norihisa
AU - Kobayashi, Higashi
AU - Saito, Nozomi
AU - Shigeno, Masanori
AU - Yamaguchi, Masahiko
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), JST CREST Grant Number JPMJCR18I4, and “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” from MEXT.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/2/13
Y1 - 2019/2/13
N2 - Alkylamide (-CONHC n H 2n+1 )-substituted benzene and its pyrene derivatives have shown a discotic hexagonal columnar liquid-crystalline phase through a one-dimensional (1D) intermolecular N-H···O hydrogen-bonding interaction, the direction of which is inverted through the application of an alternate current voltage. The polar hydrogen-bonding chains and dipole inversion reveal a ferroelectric polarization-electric field (P-E) hysteresis curve. Non-planar helicene derivatives bearing two CONHC 14 H 29 chains also indicate a ferroelectric response. The racemic helicene derivative shows a bilayer lamellar liquid-crystal phase within a temperature range of 330-420 K, whereas there is no liquid crystallinity for the optically active derivative because of the different molecular assembly structure. The racemic phase is constructed through a two-dimensional (2D) N-H···O hydrogen-bonding network, which shows ferroelectric P-E hysteresis curves at above 340 K. The collective dipole inversion in the 2D layer contributes to the ferroelectricity in the lamellar phase. The remanent polarization (P r ) of 11.1 μC cm -2 is about 6 times higher than those of the planar benzene- and pyrene-based 1D ferroelectrics. Both the density of the hydrogen-bonding site and the domain orientation in the 2D system are higher than those of the 1D columnar system.
AB - Alkylamide (-CONHC n H 2n+1 )-substituted benzene and its pyrene derivatives have shown a discotic hexagonal columnar liquid-crystalline phase through a one-dimensional (1D) intermolecular N-H···O hydrogen-bonding interaction, the direction of which is inverted through the application of an alternate current voltage. The polar hydrogen-bonding chains and dipole inversion reveal a ferroelectric polarization-electric field (P-E) hysteresis curve. Non-planar helicene derivatives bearing two CONHC 14 H 29 chains also indicate a ferroelectric response. The racemic helicene derivative shows a bilayer lamellar liquid-crystal phase within a temperature range of 330-420 K, whereas there is no liquid crystallinity for the optically active derivative because of the different molecular assembly structure. The racemic phase is constructed through a two-dimensional (2D) N-H···O hydrogen-bonding network, which shows ferroelectric P-E hysteresis curves at above 340 K. The collective dipole inversion in the 2D layer contributes to the ferroelectricity in the lamellar phase. The remanent polarization (P r ) of 11.1 μC cm -2 is about 6 times higher than those of the planar benzene- and pyrene-based 1D ferroelectrics. Both the density of the hydrogen-bonding site and the domain orientation in the 2D system are higher than those of the 1D columnar system.
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U2 - 10.1021/jacs.8b11222
DO - 10.1021/jacs.8b11222
M3 - Article
C2 - 30646681
AN - SCOPUS:85061282999
SN - 0002-7863
VL - 141
SP - 2391
EP - 2397
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 6
ER -