Search of Optimum Conditions for Sublimation Growth of Thiophene/Phenylene Co‐Oligomer Crystals

Yamao, Takeshi; Kawasaki, Yasuhiro; Ota, Satoshi; Hotta, Shu; Azumi, Reiko

doi:10.1002/masy.200651043

Cited by 7 publications

(4 citation statements)

References 9 publications

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“…A similar effect can be recognized for the alkyl substituted oligothiophenes [14]. [15]. An FET was fabricated by mounting a single crystal of BP1T-OMe on a silicone wafer covered with silicone oxide of 300 nm in thickness.…”

mentioning

confidence: 58%

“…The reaction mixture was then cooled to 5 °C and subsequently hydrolyzed with 35% hydrochloric acid (50 mL), yielding precipitates. The precipitates were washed successively with water, dilute hydrochloric acid, and methanol to give pale yellow crystals of 51.5 g (92%) of 2-(4'-methoxybiphenyl-4-yl)thiophene (15) . It is worthy of note that the 7.60-ppm line due to the central phenylene ring protons is coalesced.…”

Section: 5-bis(4'-cyanobiphenyl-4-yl)thiophene (Bp1t-cn) 4-biphenymentioning

confidence: 99%

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Synthesis of thiophene/phenylene co‐oligomers. V. Functionalization at molecular terminals toward optoelectronic device applications

Katagiri

Ota

Ohira

et al. 2007

Journal of Heterocyclic Chem

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We report the synthesis of various thiophene/phenylene co‐oligomers with a total number of thiophene and benzene (phenylene) rings of 5 and 6 with various terminal groups. Those terminal groups have been chosen from among alkyl groups, methoxy groups, trifluoromethyl groups, and cyano groups. The molecular backbone of these compounds comprises phenyl‐ or biphenylyl‐capped thiophene (or oligothiophene) or an alternating co‐oligomer. The synthesis is based on either the Suzuki coupling reaction or the Negishi coupling reaction. These reaction schemes enabled us to obtain the target compounds in high quality. In particular, the latter coupling method turned out to produce the compounds at a high yield. The terminal groups are expected to produce various functionalities based upon their electron donating character (alkyl groups and methoxy groups) or electron withdrawing character (trifluoromethyl groups and cyano groups). Additionally some of these groups bring about enhanced solubility. This will lead to the production of a diversity of modified compounds of thiophene/phenylene co‐oligomers. To give an example that demonstrates usefulness of the target compounds, we present optoelectronic data that are associated with their device applications.

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confidence: 58%

Section: 5-bis(4'-cyanobiphenyl-4-yl)thiophene (Bp1t-cn) 4-biphenymentioning

confidence: 99%

Synthesis of thiophene/phenylene co‐oligomers. V. Functionalization at molecular terminals toward optoelectronic device applications

Katagiri

Ota

Ohira

et al. 2007

Journal of Heterocyclic Chem

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“…Our apparatus and growth method are based mainly upon those described in the previous literature. [22][23][24] The apparatus consists of a glass tube and two closely aligned band heaters wound around the tube. The first heater is set at a high temperature for sublimation and the second one is for crystallization.…”

Section: Methodsmentioning

confidence: 99%

Polarized measurements of spectrally narrowed emissions from a single crystal of a thiophene/phenylene co-oligomer

Yamao

Ohira

Ota

et al. 2007

Journal of Applied Physics

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The spectrally narrowed emissions ͑SNE͒ from a flat single crystal of a thiophene/phenylene co-oligomer were investigated in a series of polarized measurements. The SNE spectra comprise of two major lines occurring at 507 and 514 nm. Of these, the former line effectively causes the emission gain narrowing by the pulse laser excitation polarized along the c axis. The intensity of the SNE is nearly isotropic with the radial directions along the flat crystal plane paralleling the bc plane. The SNE is strongly polarized along the a axis with its emission polarization ratio of the a axis to the b axis being 16.7. These polarized SNEs can be understood by the upright configuration of the molecular long axis paralleling the a axis.

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“…The construction was a kind of sublimation growth [35][36][37] and modified on the basis of that previously reported. [38][39][40] This apparatus consists of a glass tube (a test tube of 25 mm in outside diameter) and two band heaters. Several glass cylinders closely fit inside the test tube.…”

Section: Vapor-phase Crystal Growthmentioning

confidence: 99%

Exotic Optoelectronic Properties of Organic Semiconductors with Super-Controlled Nanoscale Sizes and Molecular Shapes

Hotta¹,

Yamao²,

Katagiri³

2014

j nanosci nanotechnol

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We present several aspects of thiophene/phenylene co-oligomers (TPCOs). TPCOs are regarded as a newly occurring class of organic semiconductors. These materials are synthesized by hybridizing thiophene and phenylene rings at the molecular level with their various mutual arrangements. These materials are characterized by the super-controlled nanoscale sizes and molecular shapes. These produce peculiar crystallographic structures and high-performance optical and electronic properties. The crystals of TPCOs were obtained through both vapor phase and liquid phase. In the TPCO crystals, the molecules take upright configuration. These cause large carrier mobilities of field-effect transistors and laser oscillations under optical excitations. Spectrally-narrowed emissions (SNEs) were also achieved under weak optical excitation using a mercury lamp. The light-emitting field-effect transistors using these crystals for an active layer have shown the current-injected SNEs when the device was combined with an optical cavity and operated by an alternating-current gate-voltage method. Thus the TPCO materials will play an important role in the future in the fields of nanoscale technology and organic semiconductor materials as well as their optoelectronic device applications.

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Search of Optimum Conditions for Sublimation Growth of Thiophene/Phenylene Co‐Oligomer Crystals

Cited by 7 publications

References 9 publications

Synthesis of thiophene/phenylene co‐oligomers. V. Functionalization at molecular terminals toward optoelectronic device applications

Synthesis of thiophene/phenylene co‐oligomers. V. Functionalization at molecular terminals toward optoelectronic device applications

Polarized measurements of spectrally narrowed emissions from a single crystal of a thiophene/phenylene co-oligomer

Exotic Optoelectronic Properties of Organic Semiconductors with Super-Controlled Nanoscale Sizes and Molecular Shapes

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