start-ver=1.4 cd-journal=joma no-vol=21 cd-vols= no-issue= article-no= start-page=670 end-page=679 dt-received= dt-revised= dt-accepted= dt-pub-year=2025 dt-pub=20250324 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra en-subtitle= kn-subtitle= en-abstract= kn-abstract=[n]Phenacenes ([n] = 5-7), octafluorinated at the terminal benzene rings (F8-phenacenes: F8PIC, F8FUL, and F87PHEN), were photochemically synthesized, and their electronic spectra were investigated to reveal the effects of the fluorination on the electronic features of phenacene molecules. F8-Phenacenes were conveniently synthesized by the Mallory photoreaction of the corresponding fluorinated diarylethenes as the key step. Upon fluorination on the phenacene cores, the absorption and fluorescence bands of the F8-phenacenes in CHCl3 systematically red-shifted by ca. 3-5 nm compared to those of the corresponding parent phenacenes. The vibrational progressions of the absorption and fluorescence bands were little affected by the fluorination in the solution phase. In the solid state, the absorption band of F8-phenacenes appeared in the similar wavelength region for the corresponding parent phenacenes whereas their fluorescence bands markedly red-shifted and broadened. These observations suggest that the intermolecular interactions of excited-state F8-phenacene molecules are significantly different from those of the corresponding parent molecules, most likely due to different crystalline packing motifs. en-copyright= kn-copyright= en-aut-name=IshiiYuuki en-aut-sei=Ishii en-aut-mei=Yuuki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 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=2 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=3 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=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=OkamotoHideki en-aut-sei=Okamoto en-aut-mei=Hideki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= affil-num=1 en-affil=Graduate School of Environmental, Life, Natural Science and Technology, Okayama University kn-affil= affil-num=2 en-affil=Division of Molecular Science, Graduate School of Science and Engineering, Gunma University kn-affil= affil-num=3 en-affil=Institute for Materials Chemistry and Engineering, Kyushu University kn-affil= affil-num=4 en-affil=Institute for Materials Chemistry and Engineering, Kyushu University kn-affil= affil-num=5 en-affil=Research Institute for Interdisciplinary Science, Okayama University kn-affil= affil-num=6 en-affil=Graduate School of Environmental, Life, Natural Science and Technology, Okayama University kn-affil= en-keyword=fluorescence kn-keyword=fluorescence en-keyword=fluorinated aromatics kn-keyword=fluorinated aromatics en-keyword=phenacene kn-keyword=phenacene en-keyword=photoreaction kn-keyword=photoreaction END start-ver=1.4 cd-journal=joma no-vol=20 cd-vols= no-issue= article-no= start-page=3215 end-page=3220 dt-received= dt-revised= dt-accepted= dt-pub-year=2024 dt-pub=20241209 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina en-subtitle= kn-subtitle= en-abstract= kn-abstract=A new psammaplysin derivative, ceratinadin G (1), was obtained from the Okinawan marine sponge Pseudoceratina sp., and the gross structure was clarified through spectroscopic and spectrometric analyses. The absolute configuration of compound 1 was established by comparing its NMR and ECD data with those of the known psammaplysin derivative, psammaplysin F (2). Ceratinadin G (1) is a rare nitrile containing a cyano group as aminoacetonitrile, and is the first psammaplysin derivative possessing a cyano group. In vitro assays indicated that compound 1 displayed moderate cytotoxicity against L1210 murine leukemia cells and KB epidermoid carcinoma cells. en-copyright= kn-copyright= en-aut-name=KurimotoShin-Ichiro en-aut-sei=Kurimoto en-aut-mei=Shin-Ichiro kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=InoueKouta en-aut-sei=Inoue en-aut-mei=Kouta kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=OhnoTaito en-aut-sei=Ohno en-aut-mei=Taito kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=KubotaTakaaki en-aut-sei=Kubota en-aut-mei=Takaaki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil=Faculty of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University kn-affil= affil-num=2 en-affil=Showa Pharmaceutical University kn-affil= affil-num=3 en-affil=Showa Pharmaceutical University kn-affil= affil-num=4 en-affil=Faculty of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University kn-affil= en-keyword=ceratinadin kn-keyword=ceratinadin en-keyword=cytotoxicity kn-keyword=cytotoxicity en-keyword=marine sponge kn-keyword=marine sponge en-keyword=psammaplysin kn-keyword=psammaplysin en-keyword=Pseudoceratina sp kn-keyword=Pseudoceratina sp END start-ver=1.4 cd-journal=joma no-vol=20 cd-vols= no-issue= article-no= start-page=1560 end-page=1571 dt-received= dt-revised= dt-accepted= dt-pub-year=2024 dt-pub=20240711 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor en-subtitle= kn-subtitle= en-abstract= kn-abstract=An electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines using a proton-exchange membrane (PEM) reactor was developed. Cyanoarenes were then reduced to the corresponding benzylamines at room temperature in the presence of ethyl phosphate. The reduction of nitroarenes proceeded at room temperature, and a variety of anilines were obtained. The quinoline reduction was efficiently promoted by adding a catalytic amount of p-toluenesulfonic acid (PTSA) or pyridinium p-toluenesulfonate (PPTS). Pyridine was also reduced to piperidine in the presence of PTSA. en-copyright= kn-copyright= en-aut-name=MitsudoKoichi en-aut-sei=Mitsudo en-aut-mei=Koichi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=OsakiAtsushi en-aut-sei=Osaki en-aut-mei=Atsushi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=InoueHaruka en-aut-sei=Inoue en-aut-mei=Haruka kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=SatoEisuke en-aut-sei=Sato en-aut-mei=Eisuke kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=ShidaNaoki en-aut-sei=Shida en-aut-mei=Naoki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=AtobeMahito en-aut-sei=Atobe en-aut-mei=Mahito kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= en-aut-name=SugaSeiji en-aut-sei=Suga en-aut-mei=Seiji kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=7 ORCID= affil-num=1 en-affil=Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University kn-affil= affil-num=2 en-affil=Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University kn-affil= affil-num=3 en-affil=Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University kn-affil= affil-num=4 en-affil=Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University kn-affil= affil-num=5 en-affil=Graduate School of Engineering Science and Advanced Chemical Energy Research Center, Yokohama National University kn-affil= affil-num=6 en-affil=Graduate School of Engineering Science and Advanced Chemical Energy Research Center, Yokohama National University kn-affil= affil-num=7 en-affil=Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University kn-affil= en-keyword=cyanoarene kn-keyword=cyanoarene en-keyword=nitroarene kn-keyword=nitroarene en-keyword=PEM reactor kn-keyword=PEM reactor en-keyword=pyridine kn-keyword=pyridine en-keyword=quinoline kn-keyword=quinoline END start-ver=1.4 cd-journal=joma no-vol=18 cd-vols= no-issue= article-no= start-page=1055 end-page=1061 dt-received= dt-revised= dt-accepted= dt-pub-year=2022 dt-pub=20220819 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Electrochemical hydrogenation of enones using a proton- exchange membrane reactor: selectivity and utility en-subtitle= kn-subtitle= en-abstract= kn-abstract=Electrochemical hydrogenation of enones using a proton-exchange membrane reactor is described. The reduction of enones proceeded smoothly under mild conditions to afford ketones or alcohols. The reaction occurred chemoselectively with the use of different cathode catalysts (Pd/C or Ir/C). en-copyright= kn-copyright= en-aut-name=MitsudoKoichi en-aut-sei=Mitsudo en-aut-mei=Koichi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=InoueHaruka en-aut-sei=Inoue en-aut-mei=Haruka kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=NikiYuta en-aut-sei=Niki en-aut-mei=Yuta kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=SatoEisuke en-aut-sei=Sato en-aut-mei=Eisuke kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=SugaSeiji en-aut-sei=Suga en-aut-mei=Seiji kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= affil-num=1 en-affil=Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=2 en-affil=Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=3 en-affil=Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=4 en-affil=Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=5 en-affil=Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= en-keyword=enone kn-keyword=enone en-keyword=hydrogenation kn-keyword=hydrogenation en-keyword=iridium kn-keyword=iridium en-keyword=palladium kn-keyword=palladium en-keyword=PEM reactor kn-keyword=PEM reactor END