start-ver=1.4 cd-journal=joma no-vol=10 cd-vols= no-issue=52 article-no= start-page=31547 end-page=31552 dt-received= dt-revised= dt-accepted= dt-pub-year=2020 dt-pub=20200826 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Facile synthesis of picenes incorporating imide moieties at both edges of the molecule and their application to n-channel field-effect transistors en-subtitle= kn-subtitle= en-abstract= kn-abstract=Picene derivatives incorporating imide moieties along the long-axis direction of the picene core (Cn-PicDIs) were conveniently synthesized through a four-step synthesis. Photochemical cyclization of dinaphthylethenes was used as the key step for constructing the picene skeleton. Field-effect transistor (FET) devices of Cn-PicDIs were fabricated by using ZrO2 as a gate substrate and their FET characteristics were investigated. The FET devices showed normally-off n-channel operation; the averaged electron mobility (μ) was evaluated to be 2(1) × 10−4, 1.0(6) × 10−1 and 1.4(3) × 10−2 cm2 V−1 s−1 for C4-PicDI, C8-PicDI and C12-PicDI, respectively. The maximum μ value as high as 2.0 × 10−1 cm2 V−1 s−1 was observed for C8-PicDI. The electronic spectra of Cn-PicDIs in solution showed the same profiles irrespective of the alkyl chain lengths. In contrast, in thin films, the UV absorption and photoelectron yield spectroscopy (PYS) indicated that the lowest unoccupied molecular orbital (LUMO) level of Cn-PicDIs gradually lowered upon the elongation of the alkyl chains, suggesting that the alkyl chains modify intermolecular interactions between the Cn-PicDI molecules in thin films. The present results provide a new strategy for constructing a high performance n-channel organic semiconductor material by utilizing the electronic features of phenacenes. en-copyright= kn-copyright= en-aut-name=GuoYuxin en-aut-sei=Guo en-aut-mei=Yuxin kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=YoshiokaKaito en-aut-sei=Yoshioka en-aut-mei=Kaito kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=HamaoShino en-aut-sei=Hamao en-aut-mei=Shino kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=KubozonoYoshihiro en-aut-sei=Kubozono en-aut-mei=Yoshihiro kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=TaniFumito en-aut-sei=Tani en-aut-mei=Fumito kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=GotoKenta en-aut-sei=Goto en-aut-mei=Kenta kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= en-aut-name=OkamotoHideki en-aut-sei=Okamoto en-aut-mei=Hideki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=7 ORCID= affil-num=1 en-affil=Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=2 en-affil=Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=3 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=4 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=5 en-affil=Institute for Materials Chemistry and Engineering, Kyushu University kn-affil= affil-num=6 en-affil=Institute for Materials Chemistry and Engineering, Kyushu University kn-affil= affil-num=7 en-affil=Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University kn-affil= END start-ver=1.4 cd-journal=joma no-vol=8 cd-vols= no-issue=22 article-no= start-page=7422 end-page=7435 dt-received= dt-revised= dt-accepted= dt-pub-year=2020 dt-pub=20200418 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Synthesis of [7]phenacene incorporating tetradecyl chains in the axis positions and its application in field-effect transistors en-subtitle= kn-subtitle= en-abstract= kn-abstract=Field-effect transistors (FETs) were fabricated using a new type of phenacene molecule, 3,12-ditetradecyl[7]phenacene ((C14H29)2-[7]phenacene), and solid gate dielectrics or an electric double layer (EDL) capacitor with an ionic liquid (1-butyl-3-methylimidazolium hexafluorophosphate (bmim[PF6])). The new molecule, (C14H29)2-[7]phenacene, was efficiently synthesized via the Mallory photoreaction. Its crystal structure and electronic properties were determined, using X-ray diffraction, scanning tunneling microscopy/spectroscopy (STM and STS), absorption spectroscopy, and photoelectron yield spectroscopy, which showed a monoclinic crystal lattice (space group P21 (no. 4)) and an energy gap of ∼3.0 eV. The STM image clearly showed the molecular structure of (C14H29)2-[7]phenacene, as well as the closed molecular stacking, indicative of a strong fastener effect between alkyl chains. The X-ray diffraction pattern of thin films of (C14H29)2-[7]phenacene formed on a SiO2/Si substrate suggested that the molecule stood on the surface with an inclined angle of 30° with respect to the normal axis of the surface. The FET properties were recorded in two-terminal measurement mode, showing p-channel normally-off characteristics. The averaged values of field-effect mobility, μ, were 1.6(3) cm2 V−1 s−1 for a (C14H29)2-[7]phenacene thin-film FET with a SiO2 gate dielectric and 6(4) × 10−1 cm2 V−1 s−1 for a (C14H29)2-[7]phenacene thin-film EDL FET with bmim[PF6]. Thus, higher FET performance was obtained with an FET using a thin film of (C14H29)2-[7]phenacene compared to parent [7]phenacene. This study could pioneer an avenue for the realization of high-performance FETs through the addition of alkyl chains to phenacene molecules. en-copyright= kn-copyright= en-aut-name=OkamotoHideki en-aut-sei=Okamoto en-aut-mei=Hideki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=HamaoShino en-aut-sei=Hamao en-aut-mei=Shino kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=KozasaKeiko en-aut-sei=Kozasa en-aut-mei=Keiko kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=WangYanan en-aut-sei=Wang en-aut-mei=Yanan kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=KubozonoYoshihiro en-aut-sei=Kubozono en-aut-mei=Yoshihiro kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=PanYong-He en-aut-sei=Pan en-aut-mei=Yong-He kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= en-aut-name=YenYu-Hsiang en-aut-sei=Yen en-aut-mei=Yu-Hsiang kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=7 ORCID= en-aut-name=HoffmannGermar en-aut-sei=Hoffmann en-aut-mei=Germar kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=8 ORCID= en-aut-name=TaniFumito en-aut-sei=Tani en-aut-mei=Fumito kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=9 ORCID= en-aut-name=GotoKenta en-aut-sei=Goto en-aut-mei=Kenta kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=10 ORCID= affil-num=1 en-affil=Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=2 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=3 en-affil=Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=4 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=5 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=6 en-affil=Department of Physics & Center for Quantum Technology, National Tsing Hua University kn-affil= affil-num=7 en-affil=Department of Physics & Center for Quantum Technology, National Tsing Hua University kn-affil= affil-num=8 en-affil=Department of Physics & Center for Quantum Technology, National Tsing Hua University kn-affil= affil-num=9 en-affil=Institute for Materials Chemistry and Engineering, Kyushu University kn-affil= affil-num=10 en-affil=Institute for Materials Chemistry and Engineering, Kyushu University kn-affil= END start-ver=1.4 cd-journal=joma no-vol=9 cd-vols= no-issue= article-no= start-page=4009 end-page= dt-received= dt-revised= dt-accepted= dt-pub-year=2019 dt-pub=201938 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Synthesis of the extended phenacene molecules, [10]phenacene and [11]phenacene, and their performance in a field-effect transistor en-subtitle= kn-subtitle= en-abstract= kn-abstract= The [10]phenacene and [11]phenacene molecules have been synthesized using a simple repetition of Wittig reactions followed by photocyclization. Sufficient amounts of [10]phenacene and [11]phenacene were obtained, and thin-film FETs using these molecules have been fabricated with SiO2 and ionic liquid gate dielectrics. These FETs operated in p-channel. The averaged measurements of field-effect mobility, <μ>, were 3.1(7) × 10-2 and 1.11(4) × 10-1 cm2 V-1 s-1, respectively, for [10]phenacene and [11]phenacene thin-film FETs with SiO2 gate dielectrics. Furthermore, [10]phenacene and [11]phenacene thin-film electric-double-layer (EDL) FETs with ionic liquid showed low-voltage p-channel FET properties, with <μ> values of 3(1) and 1(1) cm2 V-1 s-1, respectively. This study also discusses the future utility of the extremely extended π-network molecules [10]phenacene and [11]phenacene as the active layer of FET devices, based on the experimental results obtained. en-copyright= kn-copyright= en-aut-name=OkamotoHideki en-aut-sei=Okamoto en-aut-mei=Hideki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=HamaoShino en-aut-sei=Hamao en-aut-mei=Shino kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=EguchiRitsuko en-aut-sei=Eguchi en-aut-mei=Ritsuko kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=GotoHidenori en-aut-sei=Goto en-aut-mei=Hidenori kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=TakabayashiYasuhiro en-aut-sei=Takabayashi en-aut-mei=Yasuhiro kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=YenPaul Yu-Hsiang en-aut-sei=Yen en-aut-mei=Paul Yu-Hsiang kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= en-aut-name=LiangLuo Uei en-aut-sei=Liang en-aut-mei=Luo Uei kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=7 ORCID= en-aut-name=ChouChia-Wei en-aut-sei=Chou en-aut-mei=Chia-Wei kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=8 ORCID= en-aut-name=HoffmannGermar en-aut-sei=Hoffmann en-aut-mei=Germar kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=9 ORCID= en-aut-name=GohdaShin en-aut-sei=Gohda en-aut-mei=Shin kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=10 ORCID= en-aut-name=SuginoHisako en-aut-sei=Sugino en-aut-mei=Hisako kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=11 ORCID= en-aut-name=LiaosYen-Fa en-aut-sei=Liaos en-aut-mei=Yen-Fa kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=12 ORCID= en-aut-name=IshiiHirofumi en-aut-sei=Ishii en-aut-mei=Hirofumi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=13 ORCID= en-aut-name=KubozonoYoshihiro en-aut-sei=Kubozono en-aut-mei=Yoshihiro kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=14 ORCID= affil-num=1 en-affil= Department of Chemistry, Okayama University kn-affil= affil-num=2 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=3 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=4 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=5 en-affil= Department of Chemistry, Okayama University kn-affil= affil-num=6 en-affil=Department of Physics, National Tsing Hua University kn-affil= affil-num=7 en-affil=Department of Physics, National Tsing Hua University kn-affil= affil-num=8 en-affil=Department of Physics, National Tsing Hua University kn-affil= affil-num=9 en-affil=Department of Physics, National Tsing Hua University kn-affil= affil-num=10 en-affil=NARD Co Ltd kn-affil= affil-num=11 en-affil=NARD Co Ltd kn-affil= affil-num=12 en-affil=National Synchrotron Radiation Center kn-affil= affil-num=13 en-affil=National Synchrotron Radiation Center kn-affil= affil-num=14 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= END start-ver=1.4 cd-journal=joma no-vol=60 cd-vols= no-issue=43 article-no= start-page=151189 end-page= dt-received= dt-revised= dt-accepted= dt-pub-year=2019 dt-pub=20190920 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Fluorescence properties of amido-substituted 2,3-naphthalimides: Excited-state intramolecular proton transfer (ESIPT) fluorescence and responses to Ca2+ ions en-subtitle= kn-subtitle= en-abstract= kn-abstract= 2,3-Naphthalimide derivatives incorporating trifluoroacetamido (3a) and methansulfonamido (3b) functionalities at the 1-position were prepared and their intramolecular excited state proton transfer (ESIPT) fluorescence and responses to metal ions were investigated. Compound 3a displayed normal fluorescence in the amide form in toluene and MeCN and no response to metal cations in the corresponding amidate ion form. In contrast, compound 3b gave off dual emission assignable to normal and ESIPT fluorescence. Additionally, the amidate form of compound 3b displayed off-on fluorescence response to Ca2+. en-copyright= kn-copyright= en-aut-name=WangLei en-aut-sei=Wang en-aut-mei=Lei kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=FujiiMayu en-aut-sei=Fujii en-aut-mei=Mayu kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=NambaMisa en-aut-sei=Namba en-aut-mei=Misa kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamajiMinoru en-aut-sei=Yamaji en-aut-mei=Minoru kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=OkamotoHideki en-aut-sei=Okamoto en-aut-mei=Hideki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= affil-num=1 en-affil=Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=2 en-affil=Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=3 en-affil=Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=4 en-affil=Division of Molecular Science, Graduate School of Science and Engineering, Gunma University kn-affil= affil-num=5 en-affil=Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University kn-affil= en-keyword=Fluorescence kn-keyword=Fluorescence en-keyword=ESIPT kn-keyword=ESIPT en-keyword=Naphthalimide kn-keyword=Naphthalimide en-keyword=Ca2+ probe kn-keyword=Ca2+ probe END start-ver=1.4 cd-journal=joma no-vol= cd-vols= no-issue= article-no= start-page= end-page= dt-received= dt-revised= dt-accepted= dt-pub-year=1995 dt-pub=19950930 dt-online= en-article= kn-article= en-subject= kn-subject= en-title=ベンゼン-アレーンバイプレンマーの合成及び化学的挙動の研究 kn-title=Studies on Synthesis and Chemistry of Benzene-Arene Biplanemers en-subtitle= kn-subtitle= en-abstract= kn-abstract= en-copyright= kn-copyright= en-aut-name= en-aut-sei= en-aut-mei= kn-aut-name=岡本秀毅 kn-aut-sei=岡本 kn-aut-mei=秀毅 aut-affil-num=1 ORCID= affil-num=1 en-affil= kn-affil=岡山大学 END