Novel liquid crystals based on [1]benzothieno[3,2- b][1]benzothiophene

Kosˇata, Bedrˇich; Kozmı́k, Václav; Svoboda, Jirˇí; Novotná, Vladimı́ra; Vaneˇk, Prˇemysl; Glogarová, Milada

doi:10.1080/0267829031000097484

Cited by 73 publications

(48 citation statements)

References 31 publications

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“…[ 37,40 ] Due to its good solubility in common organic solvents (e.g., CHCl 3 , CH 2 Cl 2 , THF, and toluene), the purifi cation of the fi nal semiconductor was performed by fl ash column chromatography with silicagel and hexanes as the stationary and mobile phases, respectively. The semiconductor's chemical structure and purity were verifi ed by 1 H/ 13 C NMR spectroscopy and elemental analysis ( Figure S2, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…[1]benzothiophene (BTBT, 1 ) was performed according to the reported procedure. [ 40 ] Synthesis of ( [1]Benzothienopheno [3,2-b]benzothienophene-2,7-diyl)bis-(octan-1-one) (2) : To a solution of [1]benzothieno [3,2-b][1]benzothiophene (1.0 g, 4.16mmol) in 50 mL of anhydrous dichloromethane, AlCl 3 (3.07 g, 23 mmol) was added at −10 °C under nitrogen. The resulting mixture was stirred at −10 °C for 30 min, and then octanoylchloride (3.41 g, 21 mmol) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

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Micro‐/Nanostructured Highly Crystalline Organic Semiconductor Films for Surface‐Enhanced Raman Spectroscopy Applications

Yilmaz

Özdemir

Erdoğan

et al. 2015

Adv Funct Materials

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The utilization of inorganic semiconductors for surface‐enhanced Raman spectroscopy (SERS) has attracted enormous interest. However, despite the technological relevance of organic semiconductors for enabling inexpensive, large‐area, and flexible devices via solution processing techniques, these π‐conjugated systems have never been investigated for SERS applications. Here for the first time, a simple and versatile approach is demonstrated for the fabrication of novel SERS platforms based on micro‐/nanostructured 2,7‐dioctyl[1]benzothieno[3,2‐b][1]benzothiophene (C8‐BTBT) thin films via an oblique‐angle vapor deposition. The morphology of C8‐BTBT thin films is manipulated by varying the deposition angle, thus achieving highly favorable 3D vertically aligned ribbon‐like micro‐/nanostructures for a 90° deposition angle. By combining C8‐BTBT semiconductor films with a nanoscopic thin Au layer, remarkable SERS responses are achieved in terms of enhancement (≈108), stability (>90 d), and reproducibility (RSD < 0.14), indicating the great promise of Au/C8‐BTBT films as SERS platforms. Our results demonstrate the first example of an organic semiconductor‐based SERS platform with excellent detection characteristics, indicating that π‐conjugated organic semiconductors have a great potential for SERS applications.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Micro‐/Nanostructured Highly Crystalline Organic Semiconductor Films for Surface‐Enhanced Raman Spectroscopy Applications

Yilmaz

Özdemir

Erdoğan

et al. 2015

Adv Funct Materials

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show abstract

“…1 cm 2 /V s [5]. Furthermore, the dialkyl BTBT derivatives exhibit liquid crystalline phases, which is not surprising because the chemical modification of an extended π-conjugate system with long alkyl chains is the same strategy as that for liquid crystalline materials aimed at the enhancement of the anisotropy in molecular shape and suppression of easy crystallization [13]. We investigated the importance of liquid crystallinity in organic FET materials and showed how easy it is to fabricate uniform polycrystalline thin films by using liquid crystal thin films as a precursor [14].…”

Section: Introductionmentioning

confidence: 96%

Improved thermal stability in organic FET fabricated with a soluble BTBT derivative

Iino

Kobori

Hanna

2012

Journal of Non-Crystalline Solids

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“…C 8 -BTBT melts at~100°C, which is not high enough for the thermal processes to occur in device fabrication. C 8 -BTBT exhibits a liquid-like smectic mesophase of SmA, 33 which is responsible for the low thermal durability. This problem could be solved if the OFET materials exhibit any highly ordered smectic mesophase: because the highly ordered smectic mesophases exhibit a solid-like nature, their crystalline films can stay in film form when heated at their temperature range and go back to the crystal state when cooled down to the crystallization temperature; this gives the crystalline film high thermal durability.…”

Section: Liquid Crystalline Semiconductors For Ofets H Iino and J Hannamentioning

confidence: 99%

Liquid crystalline organic semiconductors for organic transistor applications

Iino

Hanna

2016

Polym J

101

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The recent development of materials for organic field effect transistors (OFETs), including small-molecule and polymer materials, are briefly reviewed, and the problems that remain to be solved prior to practical application and use are discussed. Liquid crystalline materials are good candidates for OFETs because of their advantageous properties over soluble small-molecule materials. Liquid crystalline materials show good solution processability for the fabrication of uniform crystalline thin films using the precursor of uniform liquid crystalline thin films. In addition, liquid crystalline materials having their highly ordered liquid crystal phases show a high thermal durability despite their high solubility. The novel liquid crystalline material 2-phenyl-7-decyl [1]benzothieno [3,2-b][1]benzothiophene exhibits a highly ordered liquid crystal phase, the Smectic E (SmE) phase, which has good solution processability for uniform crystalline thin films by the precursor of uniform SmE thin films, shows high thermal durability and solubility, and can be used for transistor devices having a high mobility, over 10 cm 2 Vs − 1 , by thermal annealing at 120°C for 5 min. Thus, liquid crystalline materials are good semiconductor materials for organic transistor applications instead of polymer materials. INTRODUCTIONMaterials for organic field effect transistors (OFETs) have attracted considerable attention since their high mobility of over 1 cm 2 Vs − 1 , comparable to that of amorphous silicon FETs, was reported in polycrystalline thin films of pentacene fabricated by vacuum evaporation. 1 OFETs are very attractive for device applications because they can be fabricated even at room temperature to create flexible electronics on plastic substrates. Recent materials research for OFETs has been focused on soluble OFET materials because of their device applications in printed electronics. In this review, the recent development of OFET materials is briefly discussed, including the use of small molecules and polymers, and the remaining problems to be solved for their practical applications are discussed. Then, a new candidate for OFET materials, that is, liquid crystals, as a self-organizing molecular semiconductor, is discussed, focusing on how liquid crystallinity can solve the existing problems, and its high potential for OFET applications is demonstrated with a highly ordered smectic liquid crystal of 2-phenyl-7-decyl[1]benzothieno [3,2-b][1] benzothiophene (Ph-BTBT-10). 2

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Novel liquid crystals based on [1]benzothieno[3,2- b][1]benzothiophene

Cited by 73 publications

References 31 publications

Micro‐/Nanostructured Highly Crystalline Organic Semiconductor Films for Surface‐Enhanced Raman Spectroscopy Applications

Micro‐/Nanostructured Highly Crystalline Organic Semiconductor Films for Surface‐Enhanced Raman Spectroscopy Applications

Improved thermal stability in organic FET fabricated with a soluble BTBT derivative

Liquid crystalline organic semiconductors for organic transistor applications

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