Alkyl-π functional molecular liquids towards soft electronics

Machida, Takashi; Nakanishi, Takashi

doi:10.1039/d1tc00998b

Cited by 16 publications

(9 citation statements)

References 50 publications

(65 reference statements)

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“…1a). Branched alkyl chains with a branch at the 2position, the so-called Guerbet chains (C n C n+4 ), are highly capable of softening and amorphizing rigid π-conjugated molecules [26][27][28][29][30] and polymers [25,31,32] and enable a wide range of elastic modulus (G') tunability. P1, with short side chains (n = 2), is a glass at room temperature (T g = 29 °C), while P2, with long side chains (n = 8), is a liquid (T g = −29 °C).…”

Section: Preparation Of π-Electretsmentioning

confidence: 99%

Stretchable π-conjugated polymer electrets for mechanoelectric generators

Shinohara

Yoshida

Pan

et al. 2022

Polym J

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Electrets are materials that retain quasi-permanent electric charges and are attracting attention as key components of batteryless micropower supplies. A chemical structure that facilitates ionization and that can stabilize these charges, such as a π-conjugated system, is expected to increase the charge density compared with that of conventional insulating polymers. Here, we report a mechanoelectric generator (MEG) (vibrational energy harvester) that uses alkylated π-conjugated polymers (Alk-CPs), which can be monopolarized either into positive or negative mode electrets. With the attachment of insulating, bulky, yet flexible alkyl side chains to the π-conjugated backbone, the poled Alk-CPs showed long charge lifetime suitable for MEGs. The elastic modulus of the electret was adjusted to approximately match that of the stretchable polyurethane substrate by blending two miscible Alk-CPs with different elastic moduli, producing a laminated film that could be stretched up to 300%. The MEG presented showed conformability when applied to a deformable object.

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Section: Preparation Of π-Electretsmentioning

confidence: 99%

Stretchable π-conjugated polymer electrets for mechanoelectric generators

Shinohara

Yoshida

Pan

et al. 2022

Polym J

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“…This synthetic approach can therefore be easily applied to a variety of π-conjugated molecules and thus is expected to greatly expand the FML library. 1,23,26 Furthermore, aggregation structures of the πconjugated moieties in FMLs are controlled by the alkyl chain substituents and their substitution positions, occasionally generating unexpected photochemical and rheological properties. 26 Recently, alkyl−π liquid compounds 1−4 containing pyrene (Figure 1a) as the functional π-moiety were synthesized, and their rheological and photochemical properties were investigated.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Functional molecular liquids (FMLs) have attracted attention as a new generation of solvent-free, nonvolatile room-temperature fluid materials , for various applications such as organic light-emitting diodes, − luminescence, − photoconduction, − molecular recognition, , and energy storage. − Recently, a synthetic strategy called alkyl−π engineering has been developed, allowing the synthesis of FMLs with prominent properties by combinations of bulky yet flexible branched-alkyl chains and optoelectronically active π-conjugated moieties. ,, The combinations lead to the formation of entropy-driven fluid states because of the suppression of intermolecular interactions between π-conjugated moieties by the alkyl chains. This synthetic approach can therefore be easily applied to a variety of π-conjugated molecules and thus is expected to greatly expand the FML library. ,, Furthermore, aggregation structures of the π-conjugated moieties in FMLs are controlled by the alkyl chain substituents and their substitution positions, occasionally generating unexpected photochemical and rheological properties …”

Section: Introductionmentioning

confidence: 99%

Liquid Structures and Diffusion Dynamics of Alkyl–Pyrene Liquids Studied by Molecular Dynamics Simulations

Yamamoto

Nakanishi

et al. 2023

J. Phys. Chem. B

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Functional molecular liquids (FMLs) based on alkylated π-conjugated molecules have attracted attention as solvent-free and nonvolatile liquid materials with prominent optoelectronic features. Recently, novel FML compounds containing pyrene as the functional core were synthesized, and their rheological and photochemical properties were investigated. Although the molecules differ only in the number of alkyl chain substituents and their substitution positions, their viscosity coefficients are largely different beyond the Stokes–Einstein relation on the assumption of identical microscopic friction, indicating that local microscopic molecular interactions are crucial for the macroscopic rheological properties. Here, we report a theoretical study on the rheological properties of the alkyl–pyrene liquids by means of atomistic molecular dynamics (MD) simulations. We performed long-time MD simulations for tens of microseconds to obtain ample statistical samples of the alkyl–pyrene liquids and analyzed their liquid structures and diffusion dynamics based on spatiotemporal correlation functions. We found the formation of characteristic local liquid structures of π–π stacking of the pyrene moieties and locally anisotropic and anomalous diffusion dynamics, which remarkably vary depending on the alkyl substituent patterns. The present results provide an atomistic insight into the macroscopic rheological properties of alkyl−π FMLs and molecular design strategy for them.

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“…Softening self-organized functional materials has effects on enhancement of molecular motion leading to the dynamic properties, such as stimuli responsiveness and transportation properties. − The softened molecular assemblies enhance the motion leading to dynamic functions. Organic layered materials, such as liquid crystals and layer-by-layer assemblies, exhibit the characteristic properties originating from the 2D anisotropy and structural flexibility. − Soft 2D materials require both the structural rigidity forming the layered structures and flexibility enhancing the dynamic properties.…”

Section: Introductionmentioning

confidence: 99%

Coatable 2D Conjugated Polymers Containing Bulky Macromolecular Guests for Thermal Imaging

Edagawa

Matsuda

Kawakubo

et al. 2022

ACS Appl. Mater. Interfaces

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Dynamic properties are derived from the structural flexibility of 2D polymers. Softening layered structures has the potential for tuning and enhancing the dynamic properties. In the present work, the flexibility of layered polydiacetylene (PDA) is tuned by the interlayer polymeric guests with different branching structures. PDA shows thermoresponsive color-change properties through shortening the effective conjugation length with molecular motion. Whereas the blue-to-red color transition is observed at certain threshold temperatures for the layered PDA without the interlayer guest, the intercalation of the bulky polymer guests lowers the starting temperature and widens the temperature range for the thermoresponsive color changes. The resultant layered composite of PDA and bulky polymer affords the homogeneous coating on substrates on the centimeter scale. The thermoresponsive color-change coating is applied to temperature-distribution imaging. The specific heat of liquids is colorimetrically estimated using the coating on the bottle. The coating on a silk cloth visualizes the temperature distribution on a simulated tissue during surgical operation using an ultrasonic coagulation cutting device. The coating can be applied to thermal imaging in a variety of fields. Moreover, the softening strategy contributes to explore dynamic properties of soft 2D materials.

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Alkyl-π functional molecular liquids towards soft electronics

Abstract: Free deformable, stretchable soft electronic devices are targeted by utilizing alkyl-π functional molecular liquids.

Cited by 16 publications

References 50 publications

Stretchable π-conjugated polymer electrets for mechanoelectric generators

Stretchable π-conjugated polymer electrets for mechanoelectric generators

Liquid Structures and Diffusion Dynamics of Alkyl–Pyrene Liquids Studied by Molecular Dynamics Simulations

Coatable 2D Conjugated Polymers Containing Bulky Macromolecular Guests for Thermal Imaging

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