Molecular design and physical properties of alkylamide-substituted 3-fold symmetric molecules

Abstract C 3-symmetric molecules incorporating alkylamide chains (−CONHCnH2n+1) form 1-dimensional (1D) columnar structures via intermolecular amide hydrogen bonding, exhibiting diverse physical properties. In these molecular systems, ferroelectricity based on amide group dipole inversion is observed, particularly pronounced in the discotic hexagonal columnar (Colh) liquid crystal phase. In systems incorporating chiral side alkyl chains, a pronounced chirality effect on molecular dynamics is observed. Cooperative dipole inversion, facilitated by unidirectional helical assembly structures, leads to the remarkable phenomenon of dramatically reduced coercive electric field. Furthermore, studies of ferroelectric–antiferroelectric mixed systems have revealed the correlation length required for ferroelectricity to emerge within 1D ferroelectric domains. This molecular design concept has been extended to various 3-fold symmetric frameworks, including triphenylamine, triphenylmethanol, triptycene, and hexadihydrotribenzo[12]annulene. Diverse assembly structure and physical property such as ferroelectricity, chirality effects, and glass formation have been discovered in these molecular systems. Alkylamide-substituted 3-fold symmetric molecules offer high design flexibility and are positioned as a molecular platform with great potential for self-assembly and property control.

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Publication Details

Journal
Chemistry Letters
Published
2025-09-25
DOI
https://doi.org/10.1093/chemle/upaf184
Primary Topic
Synthesis and properties of polymers
Type
article
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article

Molecular design and physical properties of alkylamide-substituted 3-fold symmetric molecules

Yotaro Kasahara, Takashi Takeda, Tomoyuki Akutagawa
Chemistry Letters
Synthesis and properties of polymers
article

Molecular design and physical properties of alkylamide-substituted 3-fold symmetric molecules

Yotaro Kasahara, Takashi Takeda, Tomoyuki Akutagawa
article en

Abstract

Abstract C 3-symmetric molecules incorporating alkylamide chains (−CONHCnH2n+1) form 1-dimensional (1D) columnar structures via intermolecular amide hydrogen bonding, exhibiting diverse physical properties. In these molecular systems, ferroelectricity based on amide group dipole inversion is observed, particularly pronounced in the discotic hexagonal columnar (Colh) liquid crystal phase. In systems incorporating chiral side alkyl chains, a pronounced chirality effect on molecular dynamics is observed. Cooperative dipole inversion, facilitated by unidirectional helical assembly structures, leads to the remarkable phenomenon of dramatically reduced coercive electric field. Furthermore, studies of ferroelectric–antiferroelectric mixed systems have revealed the correlation length required for ferroelectricity to emerge within 1D ferroelectric domains. This molecular design concept has been extended to various 3-fold symmetric frameworks, including triphenylamine, triphenylmethanol, triptycene, and hexadihydrotribenzo[12]annulene. Diverse assembly structure and physical property such as ferroelectricity, chirality effects, and glass formation have been discovered in these molecular systems. Alkylamide-substituted 3-fold symmetric molecules offer high design flexibility and are positioned as a molecular platform with great potential for self-assembly and property control.

Chemistry LettersVol. 54(10)
Shinshu University (JP), Tohoku University (JP), Shinshu University Hospital (JP)
Openalex Percentile: Top 77%
Synthesis and properties of polymers
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