Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals

Narazaki, Yu; Nishikawa, Hiroya; Higuchi, Hiroki; Okumura, Yasushi; Kikuchi, Hirotsugu

doi:10.1039/c7ra12465a

Cited by 6 publications

(4 citation statements)

References 47 publications

(52 reference statements)

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“…The functionalized 1,1′-binaphthol (BINOL) derivatives have been regarded as one of the most promising chiral emitters for CP-OLEDs construction due to their stable axial chiral configuration and strong chirality induction ability. − Zhao et al found that the molecular conformation of BINB- n ( n = 1–8) could be effectively controlled by the length of the bridged alkyl chains on the hydroxyl groups (significantly influenced the dihedral angles (θ) between two naphthyl rings of the BINOL), which further affected their CD annihilation or preservation behavior in the aggregated state . Narazaki et al researched the different substituent effects of bridged binaphthyl-type chiral dopants in dopant-induced chiral liquid crystals . In 2020, we constructed the induced-type CP-OLED devices from achiral fluorescence F8BT, and the CP-EL performance was greatly improved by using a pair of chiral binaphthyl-based inducers with excellent carrier mobility of pyrene moiety .…”

Section: Introductionmentioning

confidence: 99%

“…27 Narazaki et al researched the different substituent effects of bridged binaphthyl-type chiral dopants in dopant-induced chiral liquid crystals. 28 In 2020, we constructed the induced-type CP-OLED devices from achiral fluorescence F8BT, and the CP-EL performance was greatly improved by using a pair of chiral binaphthyl-based inducers with excellent carrier mobility of pyrene moiety. 29 Herein, a series of chiral binaphthyl-based enantiomers were synthesized by inserting different bridged alkyl chains into the hydroxyl groups of BINOL and were exploited to act as the chirality inducers (R/S-1 to R/S-5, Scheme 1) to fabricate CPL-active luminescent layers.…”

Section: ■ Introductionmentioning

confidence: 99%

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Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Zhang

Quan

et al. 2021

ACS Appl. Mater. Interfaces

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Chirality of 1,1′-binaphthol (BINOL) is due to the restricted rotation between two naphthalene rings, and its skeletal structure of binaphthyl unit can be further modified by choosing functionalized substituents to afford the enlarged chiral induction effect. In this paper, we designed and synthesized nine chiral binaphthyl derivatives ( R/S-1–R/S-9) as circularly polarized electroluminescence (CP-EL) inducers by inserting various bridged alkyl chains into the hydroxyl groups of BINOL or introducing functionalized substituents with different steric hindrances on the 3,3′-position of 2,2′-methylenedioxy-1,1′-binaphthalene. Their molecular conformations and CPL behaviors of nine chiral inducers were significantly dependent on the length of the alkyl chain and the degree of substituent steric hindrance, which could further regulate their chiral induction effect on achiral fluorescent polymer F8BT from small to large in the doped films. Moreover, in virtue of the planar rigid conjugated molecular conformation of R/S-1, R/S-6, and R/S-9, the amplified CPL signals (|g PL|) were detected as high as 2.36 × 10–2, 2.06 × 10–2, and 1.26 × 10–2 from blends of F8BT and these chiral inducers. The circularly polarized organic light-emitting diode (CP-OLED) device on the blends of F8BT and chiral inducers ( R/S-6) with small dihedron angle and excellent carrier mobility showed a low turn-on voltage (V on < 4.5 V), high brightness (> 10509.6 cd/m2), and maximum |g EL| value of 1.86 × 10–2 (F8BT + 5% R/S-6). This work can develop and provide a valuable reference for CP-OLED device design through chiral dopant induction.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Zhang

Quan

et al. 2021

ACS Appl. Mater. Interfaces

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“…When the chiral dopant, a class of asymmetric molecules, is added into the nematic LC, chiral nematic LC is formed. Such chiral nematic LC shows a fast-electric response and Bragg's reflection property [32][33][34]. However, the doping of chiral molecule will negatively affect the tunability of the LC material in some degree.…”

Section: Design and Analysis Of The E-crlh Tlmentioning

confidence: 99%

Reconfigurable dual-band metamaterial antenna based on liquid crystals

Che¹,

Meng²,

Lyu³

et al. 2018

J. Phys. D: Appl. Phys.

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In this paper, a novel reconfigurable dual-band metamaterial antenna with a continuous beam that is electrically steered in backward to forward directions is first proposed by employing a liquid crystal (LC)-loaded tunable extended composite right-/left-handed (E-CRLH) transmission line (TL). The frequency-dependent property of the E-CRLH TL is analyzed and a compact unit cell based on the nematic LC is proposed to realize the tunable dual band characteristics. The phase constant of the proposed unit cell can be dynamically continuously tuned from negative to positive values in two operating bands by changing the bias voltage of the loaded LC material. A resulting dual band fixed-frequency beam steering property has been predicted by numerical simulations and experimentally verified. The measured results show that the fabricated reconfigurable antenna features an electrically controlled continuous beam steering from backward −16° to forward +13° at 7.2 GHz and backward −9° to forward +17° at 9.4 GHz, respectively. This electrically controlled beam steering range turns out to be competitive with the previously reported single band reconfigurable antennas. Besides, the measured and simulated results of the proposed reconfigurable dual-band metamaterial antenna are in good agreement.

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“…The structural design of inducers allows the helicity of the polymer film that is prepared I n cholesteric LCs to be tuned. [22] Further, the helical twisting power (HTP) is defined for estimating the performance of the induction function of chiral inducers and can be given as follows:…”

Section: Introductionmentioning

confidence: 99%

Estimation of the helical twisting power of chiral inducers by time-dependent density functional theory (TD-DFT) for electrochemical polymerization in cholesteric liquid crystals

Shen

Goto

2018

Molecular Crystals and Liquid Crystals

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： Five chiral compounds were designed and synthesized using the Mitsunobu reaction to act as chiral inducers (i.e., chiral dopants) for the transformation of a nematic liquid crystal (LC) (4-n-octoxy-4ʹ-cyanobiphenyl) into a cholesteric LC. These chiral inducers contain two types of chiral alkyl chains with different kinds of achiral mesogenic cores (biphenylcarboxylate, biphenoxy, and cyanobiphenoxy. We observed that the achiral mesogenic cores affected the helical twisting power in terms of both induction strength and helicity (left-/right-hand introduction). All the ester type inducers exhibited a positive Cotton effect and right-hand helical twisting power (HTP). However, ethers exhibited a negative Cotton effect and left-hand HTP. The microscopic HTPs (β M) of these inducers demonstrate a linear relation with their optical activities (ellipticity near the absorption maximum). Further, the time-dependent density functional theory (TD-DFT) calculation using the B3LYP/6-311++G (d, p) method has been used to predict the circular dichroism spectra of these inducers. The predicted optical activity was observed to be in accordance with that observed in the experimental result. This study proposes a method for predicting the HTP of chiral inducers that can be applied to achieve polymerization in the reaction fields of cholesteric LCs.

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Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals

Cited by 6 publications

References 47 publications

Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Controllable Circularly Polarized Electroluminescence Performance Improved by the Dihedral Angle of Chiral-Bridged Binaphthyl-Type Dopant Inducers

Reconfigurable dual-band metamaterial antenna based on liquid crystals

Estimation of the helical twisting power of chiral inducers by time-dependent density functional theory (TD-DFT) for electrochemical polymerization in cholesteric liquid crystals

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