Simple molecular ferroelectrics:<i>N</i>,<i>N</i>′-dialkyl-terephthalamide derivatives in the solid phase

Kawana, Moeko; Mizoue, Ryohei; Takeda, Takashi; Hoshino, Norihisa; Akutagawa, Tomoyuki

doi:10.1039/d1tc05001j

Cited by 7 publications

(9 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The very simple molecular structure of Cn-TPA derivatives exhibits a successive solid-solid phase transition depending on the alkyl chain length (n), and ferroelectricity is detected in derivatives with longer alkyl chain lengths (n 4 10). 76 The inversion dynamics of intermolecular N-HÁ Á ÁOQhydrogen bonds are observed in thermally fluctuating flexible molecular assemblies such as the Col h liquid crystal phase. Systematically varying the alkyl chain length from n = 5 to n = 18 in Cn-TPA derivatives adjusts the balance between the hydrogen-bonding interaction of the N-HÁ Á ÁOQ group and the van der Waals interaction of the alkyl chain (Fig.…”

Section: Dynamic Alkylamide Group and Ferroelectricity In The Solid S...mentioning

confidence: 99%

See 1 more Smart Citation

Chemical design of organic ferroelectrics using dynamics of alkylamide chains

Takeda

Akutagawa

2022

Chem. Commun.

View full text Add to dashboard Cite

show abstract

Section: Dynamic Alkylamide Group and Ferroelectricity In The Solid S...mentioning

confidence: 99%

“…The very simple molecular structure of Cn-TPA derivatives exhibits a successive solid–solid phase transition depending on the alkyl chain length ( n ), and ferroelectricity is detected in derivatives with longer alkyl chain lengths ( n > 10). 76…”

Section: Dynamic Alkylamide Group and Ferroelectricity In The Solid S...mentioning

confidence: 99%

Chemical design of organic ferroelectrics using dynamics of alkylamide chains

Takeda

Akutagawa

2022

Chem. Commun.

View full text Add to dashboard Cite

show abstract

“…C14-TPA and C14-IPA did not form a Col h liquid crystal phase based on POM observations and XRD measurements; however, partial melting of the alkyl chains occurred in the high- T solid phase. The crystal structures of C5-TPA and C6-IPA formed 1D and 2D N–H···O hydrogen-bonded network structures, the patterns of which were distinct. Ferroelectric P – E hysteresis curves were observed in the high- T solid phases of C14-TPA and C14-IPA , confirming ferroelectricity.…”

Section: Discussionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

“…The inversion dynamics of intermolecular N–H···O hydrogen-bonding interactions play an important role in ferroelectrics . Similarly, ferroelectricity arising from bowl-to-bowl inversion of trithiasumanene derivatives has been reported in thermally activated molecular assemblies with high structural flexibility. − The design of molecular ferroelectrics based on such dynamic systems provides interesting functional molecular assemblies. − The control of dynamics in molecular assemblies is an important study from the viewpoint of designing multifunctionalities and design of biomimetic functions. − …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Ferroelectricity and Phase Change Memory of Bis(tetradecylamide)-Substituted Benzene Derivatives

et al. 2023

Self Cite

View full text Add to dashboard Cite

Interplay between intermolecular interactions including hydrogen bonding, halogen–halogen, and van der Waals interactions in molecular crystals leads to diverse phase transition behaviors and physical properties. Bis(tetradecylamide)-substituted benzene derivatives, terephthalamide (C14-TPA), isophthalamide (C14-IPA), and phthalamide (C14-PA), were examined, and the electric field–polarization curves of the former two crystals indicated ferroelectric hysteresis behavior in high-temperature solid phases. C14-XIPA derivatives where X = CH3, Cl, Br, or I at the 5-position of the IPA molecule were synthesized, and the effects of substituent X on the molecular assembly structure and physical properties were investigated. H- and CH3-substituted C14-IPA and C14-MeIPA formed a crystalline phase in which intermolecular amide-type N–H···O hydrogen-bonding interactions were dominant, whereas halogen-substituted C14-XIPAs formed a metastable glass phase upon cooling from the isotropic liquid. The formation of the glass phase is associated with energy competition between hydrogen bonding, halogen–halogen, and van der Waals interactions among the −CONH–, −X, and −C n H2n+1 units. The glass-crystal phase transition of C14-XIPAs (X = Cl, Br, or I) changes the refractive index under polarized optical microscopic observation, which can be utilized for phase-change memory.

show abstract

Chiral Plastic Crystal of Solid-State Dual Rotators

Sato

Takeda

Dekura

et al. 2023

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

A dual molecular rotor N-adamantyl camphor sulfonamide (ADCS) consisting of adamantane (AD) and camphor (CA) linked by a sulfonamide (−SO2NH−) bond was designed to form a chiral plastic crystal. Chiral 1S-ADCS and racemic rac-ADCS crystals exhibited a phase transition from the crystal to the plastic crystal phase upon heating at approximately 400 K, as confirmed by optical, structural, and dielectric measurements. In the plastic crystal phase, both the AD and CA units have thermally activated motional freedom and their dynamics freeze to form a low-temperature plastic crystal phase rather than a crystal phase. The most stable and metastable ADCS conformations coexist in the as-grown crystalline phase, and the dynamic behavior of the plastic crystal phase makes it difficult to recover the initial conformations necessary for the formation of the closest packing structure upon cooling, resulting in a phase transition to the plastic crystalline state. The as-grown white crystals of both 1S-ADCS and rac-ADCS exhibited weak luminescence, whereas the phase transition from glass to transparent plastic crystals changed to a non-fluorescent state.

show abstract

Simple molecular ferroelectrics:N,N′-dialkyl-terephthalamide derivatives in the solid phase

Abstract: Simple molecules of N,N'-dialkyl-1,4-benzenedicarboxamide (CnIPA) form a one-dimensional (1D) N−H•••O= hydrogen-bonding molecular assembly, which show a solid–solid phase transition through the partial melting of alkyl chains before phase transition to...

Cited by 7 publications

References 55 publications

Chemical design of organic ferroelectrics using dynamics of alkylamide chains

Chemical design of organic ferroelectrics using dynamics of alkylamide chains

Ferroelectricity and Phase Change Memory of Bis(tetradecylamide)-Substituted Benzene Derivatives

Chiral Plastic Crystal of Solid-State Dual Rotators

Contact Info

Product

Resources

About