Novel Thienyl-dibenzothiophene Oligomers End-capped by Hexylphenyl Groups as Potential Organic Semiconductor Materials

Duan, Zongfan; Yang, Zhigang; Hoshino, Daiki; Hirao, Toshio; Taguchi, Mitsumasa; Ohuch, Hirokuni; Yanagi, Yousuke; Nishioka, Yasushiro

doi:10.1080/15421406.2012.702376

Cited by 3 publications

(7 citation statements)

References 13 publications

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“…The oligomers (28HPTDBT and 37HPTDBT) were prepared according to the previously reported procedures. 19) 28HPTDBT and 37HPTDBT were purified by column chromatography and vacuum sublimation, respectively, before they were used to fabricate thin-film OFETs. The vacuum thermal deposition was performed using a miniature VACUUM SYSTEM (SANYU Electron SVC-700TM/ 700-2) in a high vacuum.…”

Section: Chemicals and Methodsmentioning

confidence: 99%

“…1). 19) 28HPTDBT and 37HPTDBT were targeted because they were anticipated to combine the high-mobility characteristics typically exhibited by phenylene-thiophene oligomers with the improved solubility/film process ability and close-packing tendencies associated with the coplanar dibenzothiophene core. The two oligomers have an identical molecular structure, except for the substituent positions of the n-hexylphenyl-2-thienyl groups in the dibenzothiophene core.…”

Section: Introductionmentioning

confidence: 99%

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Phenylene–Thiophene Oligomer Derivatives for Thin-Film Transistors: Structure and Semiconductor Performances

Duan

Ohuchi

Yanagi

et al. 2013

Jpn. J. Appl. Phys.

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Two phenylene–thiophene oligomer derivatives, 2,8-bis[5-(4-n-hexylphenyl)-2-thienyl]dibenzothiophene (28HPTDBT) and 3,7-bis[5-(4-n-hexylphenyl)-2-thienyl]dibenzothiophene (37HPTDBT), were used as active materials in thin-film organic field-effect transistors (OFETs). Although the two molecules have similar structures, they exhibited obvious differences in photophysical, crystal, π-stacking, and electrical properties. 28HPTDBT is an amorphous material and hence showed no semiconductor characteristics in its thin-film OFETs, while 37HPTDBT exhibited high crystallinity and strong π-stacking in the solid state, thus resulting in high charge carrier mobilities. The effects of gate insulators and annealing treatment on transistor performances were also investigated. Thin-film OFETs based on 37HPTDBT with an octadecanyltrichlorosilane (OTS)-treated SiO2 gate insulator exhibited excellent field-effect performances with a maximum mobility of 0.3 cm2 V-1 s-1 and a high I on/I off current ratio of 1.5×105. Although annealing treatment improved the crystallinity of the thin films, the appearance of voids (cracks) resulted in a decrease in the charge carrier mobilities in the OFETs.

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Section: Chemicals and Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Phenylene–Thiophene Oligomer Derivatives for Thin-Film Transistors: Structure and Semiconductor Performances

Duan

Ohuchi

Yanagi

et al. 2013

Jpn. J. Appl. Phys.

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“…Tetrahydrofuran (THF) and dichloromethane (DCM) were dried by distillation from lithium aluminum hydride or phosphorus pentoxide, respectively. All the organostannanes 9 and 13 and were prepared following the literature procedures for their hexyl analogues. − Bromomethyl(het)arens ( 2a–e and g ) were synthesized following the literature procedures. − …”

Section: Methodsmentioning

confidence: 99%

P₂O₅-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones

et al. 2022

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Conventional spiro-linked conjugated materials are attractive for organic optoelectronic applications due to the unique combination of their optical and electronic properties. However, spiro-linked conjugated materials with conjugation extension directed along the main axis of the molecule are still only rare examples among the vast number of spiro-linked conjugated materials. Herein, the synthesis, leading to π-extended spiro-linked conjugated materialsspiro[4.4]nonane-1,6-diones and spiro[5.5]undecane-1,7-dioneshas been developed and optimized. The proposed design concept starts from readily available malonic esters and contains several steps: double alkylation of malonic ester with bromomethylaryl(hetaryl)s; conversion of a malonic ester into the corresponding malonic acid; electrophilic spirocyclization of the latter into the annulated spiro[4.4]nonane-1,6-dione or spiro[5.5]undecane-1,7-dione in the presence of phosphorus pentoxide. On the basis of these insights, the developed method yielded spiro-linked conjugated cores fused with benzene, thiophene, and naphthalene, decorated with active halogen atoms. The structures of the synthesized spirocycles were determined by single-crystal X-ray diffraction analysis. Benzene fused spiro[4.4]nonane-1,6-dione decorated with bromine atoms was transformed into V-shape phenylene-thiophene co-oligomer type spirodimers via Stille coupling. The spiro-bis(4-n-dodecylphenyl)-2,2′-bithiophene derivative possessed high photoluminescence properties in both solution and solid state with a photoluminescence quantum yield (PL QY) of 38%.

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“…The oligomer 37HPTDBTSO was synthesized according to the previously reported procedures (23). The BHJ solar cells were fabricated by spin-coating technique.…”

Section: Fabrication Of Organic Solar Cellsmentioning

confidence: 99%

“…BHJ solar cells fabricated based on poly(3-hexylthiophene) (P3HT): [6,6]-phenyl C61 butyric acid methyl ester (PCBM) have the maximum IPCE around 500 nm (21,22). On the other hand, Duan et al reported that a BHJ solar cell based on 3,7-bis [5-(4-nhexylphenyl)-2-thienyl] dibenzothiophene -5, 5-dioxide (37HPTDBTSO) shown in Figure 1, has the maxmum IPCE around 400 nm (23,24). Thus, it is interesting to investigate if the spectral sensitivities can be braoden between 300 and 500 nm in a BHJ solar cell based on a ternary mixed solution of P3HT, 37HPTDBTSO, and PCBM.…”

Section: Introductionmentioning

confidence: 99%

Bulk-Heterojunction Solar Cells Based on Mixed Donorsof P3HT and Phenylene–Thiophene Oligomer Derivative

Okukawa

Fujii²,

Duan

et al. 2013

ECS Trans.

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Two donors with different spectral sensitivities and an accepter were used to fabricate bulk hetero-junction (BHJ) solar cells with a wider absorption range. In this research, ultraviolet and visible spectra of two donors: poly(3-hexylthiophene) (P3HT) and 3,7-bis [5-(4-n -hexylphenyl)-2-thienyl] dibenzothiophene -5, 5-dioxide (37HPTDBTSO) and accepter: [6,6]-phenyl C61 butyric acid methyl ester (PCBM) in the forms of solutions or films were investigated. Based on these results, BHJ solar cells were fabricated using a ternary mixed solution of P3HT, 37HPTDBTSO, and PCBM. The measured incident photon to charge carrier efficiency spectra indicated that the solar cell based on the two donors showed a wider spectral sensitivity range. The open circuit voltage V oc was also improved to be 0.63 V, and a short circuit current density J sc was 3.65 mA/cm 2 , and a power conversion efficiency was 0.81%.

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Novel Thienyl-dibenzothiophene Oligomers End-capped by Hexylphenyl Groups as Potential Organic Semiconductor Materials

Cited by 3 publications

References 13 publications

Phenylene–Thiophene Oligomer Derivatives for Thin-Film Transistors: Structure and Semiconductor Performances

Phenylene–Thiophene Oligomer Derivatives for Thin-Film Transistors: Structure and Semiconductor Performances

P₂O₅-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones

Bulk-Heterojunction Solar Cells Based on Mixed Donorsof P3HT and Phenylene–Thiophene Oligomer Derivative

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Novel Thienyl-dibenzothiophene Oligomers End-capped by Hexylphenyl Groups as Potential Organic Semiconductor Materials

Cited by 3 publications

References 13 publications

Phenylene–Thiophene Oligomer Derivatives for Thin-Film Transistors: Structure and Semiconductor Performances

Phenylene–Thiophene Oligomer Derivatives for Thin-Film Transistors: Structure and Semiconductor Performances

P2O5-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones

Bulk-Heterojunction Solar Cells Based on Mixed Donorsof P3HT and Phenylene–Thiophene Oligomer Derivative

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P₂O₅-Promoted Cyclization of Di[aryl(hetaryl)methyl] Malonic Acids as a Pathway to Fused Spiro[4.4]nonane-1,6-Diones