Effects of Substituted Alkyl Chain Length on Solution-Processable Layered Organic Semiconductor Crystals

Inoue, Satoru; Minemawari, Hiromi; Tsutsumi, Jun; Chikamatsu, Masayuki; Yamada, Toshikazu; Horiuchi, Sachio; Tanaka, Mutsuo; Kumai, Reiji; Yoneya, Makoto; Hasegawa, Tatsuo

doi:10.1021/acs.chemmater.5b00810

Cited by 150 publications

(213 citation statements)

References 31 publications

(42 reference statements)

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“…[28] The attachment of side chains produce additional interactions between the OSC chains and solvent, and the flexibility of side chains may impede the formation of a solid state. The lengths, [30][31][32][33][34] bulkiness, [29,35,36] and number density [37] of the side chains as well as the types of functional groups [38] in the side chains and the positions on the backbone to which the side chains are attached have all been found to affect the solubility of the molecule. The lengths, [30][31][32][33][34] bulkiness, [29,35,36] and number density [37] of the side chains as well as the types of functional groups [38] in the side chains and the positions on the backbone to which the side chains are attached have all been found to affect the solubility of the molecule.…”

Section: Solubility In Solventsmentioning

confidence: 99%

“…[47,48] Low-molecularweight polystyrene (PS) oligomer also has been employed as side chains for n-type naphthalene diimide (NDI)-based conjugated polymers (Figure 3d). [30] Copyright 2015, American Chemical Society. The authors attributed the improved stability to the covalently attached PS chains serving as a molecular encapsulating layer around the conjugated polymer backbone, similar to results by Katz and co-workers using fluoroalkyl www.advelectronicmat.de Adv 14) in various organic solvents: toluene (red , purple ), anisole (blue ), and chlorobenzene (green ) at 20 °C.…”

Section: Solubility In Solventsmentioning

confidence: 99%

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Effective Use of Electrically Insulating Units in Organic Semiconductor Thin Films for High‐Performance Organic Transistors

Kang

Qiu

et al. 2016

Adv Elect Materials

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The electrical properties of organic semiconductors (OSCs), whether they are conjugated small molecules or polymers, can be tailored by incorporating electrically insulating units (EIUs), which are organic moieties consisting of nonconjugated units. EIUs can be introduced to a thin film by synthetically connecting them to the otherwise conjugated OSC molecules or by blending them in as separate EIU molecules with the OSCs during the thin‐film fabrication process. The engineered EIUs are capable of imparting various additional functions to the OSC thin film and improving their electrical properties. In this review article, a comprehensive overview of various effects of EIUs on OSC thin films and their consequent electrical performance when used as active layers in organic field‐effect transistors (OFETs) is provided. A broad range of studies of the synthetic approaches of incorporating EIUs, such as those using side chains, block copolymers, and conjugation‐break spacers, and of the blending approaches with organic insulators is discussed. Finally, a brief summary and perspectives for future research in this field are presented.

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Section: Solubility In Solventsmentioning

confidence: 99%

Section: Solubility In Solventsmentioning

confidence: 99%

Effective Use of Electrically Insulating Units in Organic Semiconductor Thin Films for High‐Performance Organic Transistors

Kang

Qiu

et al. 2016

Adv Elect Materials

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“…Here, we present an alternative approach for producing highly stable and functional SMBs, utilizing an extended π‐electron framework (πCore) that considerably enhances intermolecular attractive forces within bilayers. Recently, some asymmetric rod‐like organic molecules developed for soluble or printable organic semiconductors, such as 2‐phenyl7‐alkylated‐[1]benzothieno[3,2‐b][1]benzothiophene (Ph‐BTBT‐C n ; n ≥ 5) ( Figure a), have been reported to exhibit very high layered crystallinity associated with the formation of bilayer‐type layered herringbone (LHB) packing motifs, as presented in Figre b . The crystals of this compound feature bilayer units composed of antiparallelly aligned polar monomolecular layers, resulting in head‐to‐head contact of πCores.…”

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confidence: 99%

Semiconductive Single Molecular Bilayers Realized Using Geometrical Frustration

et al. 2018

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A unique solution-based technology to manufacture self-assembled ultrathin organic-semiconductor layers with ultrauniform single-molecular-bilayer thickness over an area as large as wafer scale is developed. A novel concept is adopted in this technique, based upon the idea of geometrical frustration, which can effectively suppress the interlayer stacking (or multilayer crystallization) while maintaining the assembly of the intralayer, which originates from the strong intermolecular interactions between π-conjugated molecules. For this purpose, a mixed solution of extended π-conjugated frameworks substituted asymmetrically by alkyl chains of variable lengths (i.e., (πCore)-C 's) is utilized for the solution process. A simple blade-coating with a solution containing two (πCore)-C 's with different alkyl chain lengths is effective to provide single molecular bilayers (SMBs) composed of a pair of polar monomolecular layers, which is analogical to the cell membranes of living organisms. It is demonstrated that the chain-length disorder does not perturb the in-plane crystalline order, but acts effectively as a geometrical frustration to inhibit multilayer crystallization. The uniformity, stability, and size scale are unprecedented, as produced by other conventional self-assembly processes. The obtained SMBs also exhibit efficient 2D carrier transport as organic thin-film transistors. This finding should open a new route to SMB-based ultrathin superflexible electronics.

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“…The issue of flexible chain length in defining material characteristics has been discussed multiple times for semiconducting and/or supramolecular materials. [22,[24][25][26] However, comparatively few works have addressed structureproperty relations of molecular ferroelectrics in a systematic manner. [8,19,27] One of the few studies focusing on proper organic ferroelectric materials is by Kishikawa et al, who probed ferroelectric columnar hexagonal liquid crystalline urea with C 4 H 9 to C 16 H 33 long alkyl chains.…”

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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Effects of Substituted Alkyl Chain Length on Solution-Processable Layered Organic Semiconductor Crystals

Cited by 150 publications

References 31 publications

Effective Use of Electrically Insulating Units in Organic Semiconductor Thin Films for High‐Performance Organic Transistors

Effective Use of Electrically Insulating Units in Organic Semiconductor Thin Films for High‐Performance Organic Transistors

Semiconductive Single Molecular Bilayers Realized Using Geometrical Frustration

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

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