Novel Low-molecular-weight Organic Gels: N,N′,N″-Tristearyltrimesamide/Organic Solvent System

Yasuda, Yoshiaki; Iishi, Eiichi; Ishiguro, Hiroshi; Shirota, Yasuhiko

doi:10.1246/cl.1996.575

Cited by 107 publications

(104 citation statements)

References 12 publications

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“…200,201 The molecules arrange themselves in columns via 3-fold intermolecular hydrogen bonding as proven by X-ray diffraction 202 and infrared spectroscopy. The weak arene-arene interactions of the single central benzene group are subordinate to the strong 3-fold hydrogen bonding.…”

Section: B Hydrogen Bondingmentioning

confidence: 99%

“…These results are analogous to those obtained in chiral polymers with covalent bonds in the main chain 204 and are explained by a strong intracolumnar cooperative effect via directional hydrogen bonding in polymers with a very high DP. At higher concentrations, the long columns gelate the solvent via lateral intercolumnar interactions, 200,201 reminiscent of the behavior of rigid-rod covalent polymers such as polyaramides and poly(γ-benzyl-L-glutamate). 205 Cis-1,3,5-cyclohexanetricarboxamides (42) are another example of discotic molecules assembling in columns via intermolecular hydrogen bonding ( Figure 24).…”

Section: B Hydrogen Bondingmentioning

confidence: 99%

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Supramolecular Polymers

et al. 2001

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I. Introduction 4071 II. The Term Supramolecular Polymers 4071 III. General Aspects of Supramolecular Polymers 4073 IV. Supramolecular Polymers Based on Hydrogen Bonding 4073 A. Strength of Hydrogen Bonds 4073 B. Hydrogen Bonding Enforced by Liquid Crystallinity 4075 C. Hydrogen Bonding Enforced by Phase Separation 4076 D. Strong Dimerization of Multiple Hydrogen-Bonding Units 4077 E. Ureidopyrimidinone-Based Polymers 4079 V. Supramolecular Polymers Based on Discotic Molecules 4081 A. Arene−Arene Interactions 4082 1. Triphenylenes 4082 2. Phthalocyanines and Porphyrins 4083 3. Helicenes 4084 4. m-Phenylene Ethynylene Oligomers 4084 5. Other Systems 4085 6. Chromonics 4086 B. Hydrogen Bonding 4086 C. Arene−Arene Interactions and Hydrogen Bonding 4087 1. Guanine and Pterine Derivatives 4087 2. Hydrogen-Bonded Pairs 4089 3. Complexation of Tetrazoles with 1,3,5-Tris (4,5-dihydroimidazol-2-yl)benzene 4089 4. C 3 -Symmetrical Discotic Molecules 4090 VI. Supramolecular Coordination Polymers and Miscellaneous Systems 4091 VII. Conclusions and Outlook 4094 VIII. Acknowledgments 4094 IX. References and Notes 4094

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Section: B Hydrogen Bondingmentioning

confidence: 99%

Section: B Hydrogen Bondingmentioning

confidence: 99%

Supramolecular Polymers

et al. 2001

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“…Initially BTA has attracted a lot of interest due to structure-related strong intermolecular interaction and the resultant formation of supramolecular polymers in solution, the ability to create gels as well as rigid nanofibers. [31][32][33][34] The ferroelectric behavior, however, is a relatively new finding. [9,35] Fitié et al were first to probe BTA homologues with 18, 10, and 6 carbons-long alkyl chain (BTA-C18, BTA-C10, and BTA-C6).…”

mentioning

confidence: 99%

Tuning the Ferroelectric Properties of Trialkylbenzene‐1,3,5‐tricarboxamide (BTA)

Urbanavičiūtė

Meng

Cornelissen

et al. 2017

Adv Elect Materials

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This study demonstrates how simple structural modification of a prototypical organic ferroelectric molecule can be used to tune its key ferroelectric properties. In particular, it is found that shortening the alkyl chain length of trialkylbenzene-1,3,5-tricarboxamide (BTA) from C18H37 to C6H13 causes an increase in depolarization activation energy (approximate to 1.1-1.55 eV), coercive field (approximate to 25-40 V mu m(-1)), and remnant polarization (approximate to 20-70 mC m(-2)). As the polarization enhancement far exceeds the geometrically expected factor, these observations are attributed to an increase in the intercolumnar interaction. The combination of the mentioned characteristics results in a record polarization retention time of close to three months at room temperature for capacitor devices of the material having the shortest alkyl chain. The long retention and the remnant polarization that is as high as that of P(VDF:TrFE) distinguish the BTA-C6 material from other small molecular organic ferroelectrics and make it a perspective choice for applications that require cheap, flexible, and lightweight ferroelectrics.

Funding Agencies|NWO Nano program; Vetenskapsradet; Swedish Government Strategic Research Area in Materials Science on Functional Materials at the Linkping University (Faculty Grant SFO Mat LiU) [2009 00971]

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“…[15][16][17] However, it seems that these systems are not suitable for lithium ion battery applications, because it seems that the existence of the hydrogen bonding networks in the gel fibers decreases the electrochemical stability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Physical Properties of Organogels based on Low Molecular Weight Gelators: 4-(2-perfluoroalkyl)ethylthiobenezene Derivatives

Iuchi¹,

Morita²,

Hirakawa³

et al. 2009

ECS Trans.

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Several derivatives for 4-(2-perfluoroalkyl)ethylthiobenzene were prepared and their gelation properties were investigated. The alkyl and alkylene derivatives formed organogels with polar and nonpolar organic solvents such as alcohols, tolunene, N,Ndimethylformamide, acetonitrile and propylenecarbonate. The thermal properties for these organogels are revealed to be thermoreversible physical gels. Furthermore, organogel electrolyte using alkyl derivative was prepared from LiPF 6 as a supporting electrolyte and mixed solvent of ethylene carbonate and dimethyl carbonate, and the ionic conductivities of gel electrolyte and that of the corresponding electrolyte solution were examined.

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Novel Low-molecular-weight Organic Gels: N,N′,N″-Tristearyltrimesamide/Organic Solvent System

Cited by 107 publications

References 12 publications

Supramolecular Polymers

Supramolecular Polymers

Tuning the Ferroelectric Properties of Trialkylbenzene‐1,3,5‐tricarboxamide (BTA)

Synthesis and Physical Properties of Organogels based on Low Molecular Weight Gelators: 4-(2-perfluoroalkyl)ethylthiobenezene Derivatives

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