Azaborine Compounds for Organic Field‐Effect Transistors: Efficient Synthesis, Remarkable Stability, and BN Dipole Interactions

Wang, Xiaoye; Lin, Haoran; Lei, Ting; Yang, Dong-Chu; Zhuang, Fang‐Dong; Wang, Jieyu; Yuan, Si-Chun; Pei, Jian

doi:10.1002/anie.201209706

Cited by 251 publications

(125 citation statements)

References 63 publications

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“…In accordance with recent investigation, the polymers with lowest spacer lengths i.e., poly(chol‐3‐MMA‐ co ‐MMA) and poly(chol‐3‐MMA) showed higher values of dielectric constants. Likewise, Wang et al . investigated OFET using two different azaborine compounds with varying lengths of alkyl side chains and obtained higher field effect mobility values and performance for the case of devices realized using compounds with lower length of side chain similar to our findings.…”

Section: Resultssupporting

confidence: 87%

Methacrylate based side chain liquid crystalline polymers with pendant cholesterol group: Preparation and investigation of electrical conductivity mechanism

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Çakırlar

Bayır

et al. 2017

J of Applied Polymer Sci

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Methacrylate based side‐chain liquid crystalline polymers (SCLCP) bearing cholesterol pendant moieties with various lengths of aliphatic spacer were synthesized and their electrical conductivity mechanism was studied for their possible applications in elastic microelectronic devices. All the polymers exhibited liquid crystalline behavior of broken focal‐conic fan texture of smectic phase. The dielectric properties of polymers were investigated by impedance spectroscopic technique in the frequency range of 100 Hz to 15 MHz at room temperature. Alternating current (AC) conductivity ( σAC) of the liquid crystalline polymeric films was observed to vary with angular frequency, ω as ωS with s < 2. Detailed conductivity analysis revealed that the conductivity of the polymeric films follows quantum mechanical tunneling and correlated barrier hoping conductivity mechanisms at low frequency regime, whereas it obeys super linear power law and direct current conductivity mechanisms at high frequency region. The investigation of the SCLC polymeric films helped to propose a model system for their possible potential applications. In the light of this study, the SCLC polymers will be employed as the gate insulator for organic field effect transistor applications, such as large area flexible arrays or as other advanced microelectronic devices that have superior performance. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45207.

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Section: Resultssupporting

confidence: 87%

Methacrylate based side chain liquid crystalline polymers with pendant cholesterol group: Preparation and investigation of electrical conductivity mechanism

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Çakırlar

Bayır

et al. 2017

J of Applied Polymer Sci

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“…The shortest distance between boron and nitrogen atoms from neighboring molecules is ∼4.6 Å, revealing weak dipole−dipole interactions comparable with those of other azaborines (∼6.7 Å). 12 Compound 3b shows a herringbone packing motif consisting of slipped stacked columns tilted at an angle of ∼70°. The distance of the neighboring layers is ∼3.9 Å, without the obvious face-to-face π−π stacking interactions observed.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Accordingly, variation of the relative positions of boron and nitrogen atoms in a BN unit significantly affects the dipole moment of a BN-embedded aromatic compound. 12 −15 In our previous work, we have reported a series of BNheteroacenes featuringa a p-phenylenediamine core fused with versatile aromatic rings in the bilateral sides and explored their application as the host materials in the device fabrication of blue OLEDs (Figure 1). 16 However, the BN-embedded compounds with multiple boron atoms attached on one aromatic unit of the main backbone, have been rarely reported, most probably because multifold electrophilic borylation in one aromatic unit is too sluggish.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Properties of C_2h-Symmetric BN-Heteroacenes Tailored through Aromatic Central Cores

et al. 2015

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The 2-fold successive electrophilic borylation on one aromatic central core led to a series of C(2h)-symmetric BN-heteroacenes in excellent yields. For the first time, we introduced trimethylsilyl (TMS) as either leaving group or oriented group for efficiently improving the preparation of BN-embedded polycyclic aromatic hydrocarbons (PAHs). The physical properties of the as-synthesized BN-heteroacenes in either solid state or solution can be finely tuned through the position isomerization or the fused ring numbers of the aromatic central core.

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“…On the other hand, the vacant p orbital of the boron atom can coordinate with the electron pair of the Lewis basic atom to form a Lewis acid/base pair, which leads to intriguing π‐conjugated systems (tetracoordinate borane) that display narrow band gaps, photoswitchable properties, and enhanced electron‐accepting abilities . Accordingly, various organoboron π‐conjugated molecules and polymers have been developed for organic optoelectronic materials and devices …”

Section: Introductionmentioning

confidence: 99%

Effects of the Substituents of Boron Atoms on Conjugated Polymers Containing B←N Units

Wang

Dou

et al. 2018

Chemistry A European J

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Organoboron chemistry is a new tool to tune the electronic structures and properties of conjugated polymers, which are important for applications in organic optoelectronic devices. To investigate the effects of substituents of boron atoms on conjugated polymers, we synthesized three conjugated polymers based on double B←N-bridged bipyridine (BNBP) with various substituents on the boron atoms. By changing the substituents from four phenyl groups and two phenyl groups/two fluorine atoms to four fluorine atoms, the BNBP-based polymers show blue-shifted absorption spectra, decreased LUMO/HOMO energy levels, and enhanced electron affinities, as well as increased electron mobilities. Moreover, these BNBP-based polymers can be used as electron acceptors for all-polymer solar cells. These results demonstrate that substituents of boron atoms can effectively modulate the electronic properties and applications of conjugated polymers.

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Azaborine Compounds for Organic Field‐Effect Transistors: Efficient Synthesis, Remarkable Stability, and BN Dipole Interactions

Cited by 251 publications

References 63 publications

Methacrylate based side chain liquid crystalline polymers with pendant cholesterol group: Preparation and investigation of electrical conductivity mechanism

Methacrylate based side chain liquid crystalline polymers with pendant cholesterol group: Preparation and investigation of electrical conductivity mechanism

Synthesis and Properties of C_2h-Symmetric BN-Heteroacenes Tailored through Aromatic Central Cores

Effects of the Substituents of Boron Atoms on Conjugated Polymers Containing B←N Units

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Azaborine Compounds for Organic Field‐Effect Transistors: Efficient Synthesis, Remarkable Stability, and BN Dipole Interactions

Cited by 251 publications

References 63 publications

Methacrylate based side chain liquid crystalline polymers with pendant cholesterol group: Preparation and investigation of electrical conductivity mechanism

Methacrylate based side chain liquid crystalline polymers with pendant cholesterol group: Preparation and investigation of electrical conductivity mechanism

Synthesis and Properties of C2h-Symmetric BN-Heteroacenes Tailored through Aromatic Central Cores

Effects of the Substituents of Boron Atoms on Conjugated Polymers Containing B←N Units

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Synthesis and Properties of C_2h-Symmetric BN-Heteroacenes Tailored through Aromatic Central Cores