Effects of alkyl chain on the liquid crystalline properties of [1]benzothieno[3,2-b][1]benzothiophene-based organic semiconductors

Park, Woobyung; Yun, Chang-Koo; Yun, Seungjae; Lee, Jaejin; Bae, Sangwok; Ho, Dongil; Kim, Jaeyong; Seo, Sang‐Hun

doi:10.1016/j.orgel.2022.106508

Cited by 2 publications

(2 citation statements)

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“…Among the variety of conjugated small molecules, symmetric aromatic hydrocarbon derivatives represent a convenient model for the fundamental study of "structure-property" relationships due to their condensed π-systems, known molecular packing extracted from X-ray data, low concentration of defects, and hence, outstanding charge carrier mobility and luminescent properties [5][6][7]. To tune a crystalline structure of organic semiconductors, several approaches were suggested and extensively exploited: variation of a conjugated framework [8][9][10][11], introduction of substituents [12][13][14][15][16][17], polymorphism [18][19][20][21][22][23], cocrystallization [24][25][26][27][28], template-induced [4,[29][30][31] and specific crystallizations [22,[32][33][34][35][36] allowing the control of crystal orientation on a substrate, and morphology. Polymorphism is considered to be one of the most powerful approaches in material science and pharmaceutical engineering for the study of "structure-activity" relationships and control of the properties of a given compound without changing its chemical structure [37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Additive-Assisted Crystallization of 9,10-Diphenylanthracene

Sonina,

Cheshkina,

Kazantsev

2023

Crystals

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Crystallization control of organic conjugated small molecules is in high demand for the engineering of functional materials in organic optoelectronics. Here, we report solution additive-assisted crystallization of a model non-planar aromatic hydrocarbon derivative 9,10-diphenylanthracene. Among the studied series of related aromatic hydrocarbons comprising pyrene, perylene, anthracene, tetracene, and rubrene, only tetracene revealed clear reproducible effects allowing one to perform selective crystallization of metastable 9,10-diphenylanthracene polymorphs. Additionally, crystallization of 9,10-diphenylanthracene and pyrene produced a stoichiometric co-crystal (PYR–DPA) having a segregated layered molecular packing with alternating 9,10-diphenylanthracene and pyrene layers. Remarkably, the molecular packing of pyrene within the co-crystal is unique and represented by the herringbone motif, whereas the molecular packing in known pyrene polymorphs is represented by π-stacked molecules. The co-crystal also demonstrated a bright photoluminescence with a photoluminescence quantum yield of 51%. Considering the morphology of 9,10-diphenylanthracene crystals obtained and crystal structures of PYR–DPA co-crystal and tetracene, we have proposed the mechanism of additive-assisted polymorphism based on the inhibition of (111) facet of α-DPA and promoting of the layered structure crystallization corresponding to metastable polymorphs (β- and γ-DPA). We highlight the additive-assisted crystallization approach as a powerful tool for the crystal engineering of functional materials for organic optoelectronics.

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Section: Introductionmentioning

confidence: 99%

Additive-Assisted Crystallization of 9,10-Diphenylanthracene

Sonina,

Cheshkina,

Kazantsev

2023

Crystals

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“…[15] Indeed, thienoacene-based derivatives, comprising fused rings in a ladder-type molecular structure, present a highly delocalized structure and low-lying highest occupied molecular orbital (HOMO) energy level, affording outstanding electrical performance and stability. [16][17][18][19][20][21][22][23] In addition, strong SÀ S and π-π intermolecular interactions of thienoacene-based derivatives have been known to enhance large intermolecular orbital overlap in the solid state and promote good charge transport characteristics. [24][25][26] Among thienoacene-based derivatives, dithieno[3,2-b : 2',3'd]thiophene (DTT)-based compounds are one of the promising candidates as active materials in high performance OFETs.…”

Section: Introductionmentioning

confidence: 99%

Development and Characterization of Solution‐Processable Dithieno[3,2‐b : 2’,3’‐d]thiophenes Derivatives with Various End‐capped Groups for Organic Field‐Effect Transistors

Kang

Jang

et al. 2022

ChemPlusChem

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In this paper, four organic materials based on dithieno[3,2b : 2',3'-d]thiophene (DTT) core structure with end-capping groups (phenyl and thienyl) and linker (acetylenic and olefinic) between DTT-core and end-capping groups were synthesized and characterized as solution-processable organic semiconductors (OSCs) for organic field-effect transistors (OFETs). Thermal, optical, and electrochemical properties of the corresponding materials were determined. Next, all DTT-derivatives were coated by solution-shearing method, and the thin-film microstructures and morphologies were investigated. To investigate the electrical performance of four newly synthesized DTTderivatives, bottom-gate/top-contact OFETs were fabricated and characterized in ambient condition. It was found that substitution of acetylenic for olefinic linkers between DTT-cores and end-capping groups enhanced device performance. Especially, the resulting OFETs based on the compound containing phenylacetylene exhibited the highest hole mobility of 0.15 cm 2 /Vs and current on/off ratio of ~10 6 , consistent with film morphology and texture showing long range interconnected crystalline grains and strong diffraction peaks.

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Effects of alkyl chain on the liquid crystalline properties of [1]benzothieno[3,2-b][1]benzothiophene-based organic semiconductors

Cited by 2 publications

References 59 publications

Additive-Assisted Crystallization of 9,10-Diphenylanthracene

Additive-Assisted Crystallization of 9,10-Diphenylanthracene

Development and Characterization of Solution‐Processable Dithieno[3,2‐b : 2’,3’‐d]thiophenes Derivatives with Various End‐capped Groups for Organic Field‐Effect Transistors

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