Synthesis of Oligo(1,8‐pyrenylene)s: A Series of Functional Molecular Liquids

Walsh, Joshua C.; Hogan, David T.; Williams, Kerry‐Lynn M.; Brake, Simon; Venkataramana, Gandikota; Misener, Tara A.; Wallace, Brandon J.; Johnson, Richard P.; Thompson, David W.; Zhao, Yuming; Wagner, Brian D.; Bodwell, Graham J.

doi:10.1002/cplu.201900133

Cited by 4 publications

(3 citation statements)

References 43 publications

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“…Those broader and smoother spectra with almost vanished vibronic sub‐bands in 1[2,4‐C 8 C 12 ] and 1[2,5‐C 8 C 12 ] might be due to their greater torsional flexibility [14] . Another hypothesis was the ‘rotamer effect’ resulting from the unrestricted single C−C bond rotation between the vinylene unit and the terminal phenyl rings, and each rotamer might have exhibited a different degree of conjugation [4c,24] …”

Section: Resultsmentioning

confidence: 99%

Quest for a Rational Molecular Design of Alkyl‐Distyrylbenzene Liquid by Substitution Pattern Modulation**

Zheng

Nagura

Takaya

et al. 2023

Chemistry A European J

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Alkyl-π functional molecular liquids (FMLs) are of interest for fabricating soft electronic devices due to their fluidic nature and innate optoelectronic functions from the πconjugated moiety. However, predictable development of alkyl-π FMLs with the desired liquid and optoelectronic properties is challenging. A series of alkyl-distyrylbenzene (DSB) liquids was studied in terms of the substituent position effect by attaching 2-octyldodecyl chains at (2,4-), (2,5-), (2,6-), and (3,5-). The effect of the alkyl chain length was investigated by attaching 2-hexyldecyl, 2-decyltetradecyl (C 10 C 14 ), and 2-dodecylhexadecyl at the (2,5-) substituent position. The 2,5-C 10 C 14 substituent pattern constructed a superior alkyl-DSB liquid with a lower viscosity, intrinsic optical properties, and high thermal-and photo-stabilities. The discovered 2,5-C 10 C 14 was applied to dicyanostyrylbenzene and comparable liquid physical and optical superiorities were confirmed. This molecular design is useful for creating alkyl-π FMLs with the aforementioned advantages, which are applicable for deformable and flowable optoelectronic devices.

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Section: Resultsmentioning

confidence: 99%

Quest for a Rational Molecular Design of Alkyl‐Distyrylbenzene Liquid by Substitution Pattern Modulation**

Zheng

Nagura

Takaya

et al. 2023

Chemistry A European J

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“…Experimentally, those groups were shown to be racemic. 27,50 In the present simulation systems, the atropisomers were evenly mixed. Preliminary simulations at 300 K confirmed that the atropisomers of the phenyl group were exchangeable by thermal fluctuation.…”

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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“…Semiconducting LCs have common molecular architecture: rigid π-conjugated units with soft side chains. Over the last decade, our group [1][2][3][4][5][6][7][8][9] and many others [10][11][12][13][14][15][16][17][18][19][20][21][22][23] have inherited this molecular design concept and focused not only on the highly ordered, supramolecular self-assembled structure, but also on the disordered and fluid properties under precisely controlled intermolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Conjugated Polymer Fluids with Optical Functions

et al. 2021

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Solvent-free fluidic materials possessing optoelectronic functions are expected to be major components in soft electronics applications. Conjugated polymers are promising targets for this purpose and their design approaches are classified into three types with respect to their structure: conjugation breaking (Type I), copolymerization with flexible polymers (Type II), and side chain engineering (Type III). In this short review, we highlight several early attempts to produce Type III conjugated polymers. We also present fully characterized Type III fluids recently developed by our group, with a brief summary of the structure–property relationship and fluidity-oriented functions.Introduction1 Polymer Design1.1 Fluidity of Polymeric Materials1.2 Type III CPs with T g < 25 °C1.3 Fluidification of Polyfluorenes1.4 Effect of Side Chain Length2 Fluidity-Oriented Functions2.1 Mechanofluorochromism2.2 Consistent Luminescence in Wide Range of Elastic Moduli2.3 Prediction of ViscoelasticityConclusions and Outlook

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Synthesis of Oligo(1,8‐pyrenylene)s: A Series of Functional Molecular Liquids

Cited by 4 publications

References 43 publications

Quest for a Rational Molecular Design of Alkyl‐Distyrylbenzene Liquid by Substitution Pattern Modulation**

Quest for a Rational Molecular Design of Alkyl‐Distyrylbenzene Liquid by Substitution Pattern Modulation**

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

Solvent-Free Conjugated Polymer Fluids with Optical Functions

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