Interdisciplinary Research Center for Catalytic Chemistry > Teams > Functional Group Transformation Team

Functional Group Transformation Team

Various useful properties and functions of materials are appeared from their molecular frames and functional groups of which the materials consist. This group aims to contribute following three fields of catalysis chemistry related with transformation of molecular frames and functional groups: catalytic transformation of renewable resources, environmentally benign catalytic addition of small molecules, and development of new materials for high performance devices.

Team Leader, Dr. Ken-ichi Tominaga(D.Sci)

Theme

  • Synthesis of Useful Chemicals from Biomass
  • Alcohol Synthesis Using Carbon Dioxide
  • New Synthesis of Phosphorescent Materials for Organic Light-Emitting Diodes (OLEDs)
  • Molecular Design of Soft-material-based Functional Probes as for Green Sustainable Chemistry
  • Molecular Robotics
  • Molecular Tweezers

Synthesis of Useful Chemicals from Biomass

We have developed a new catalyst which directly converts cellulose, a main component of plants, into levulinic acid esters in good yields. Levulinic acid is promising as a key building block for fuels, polymers, and fine chemicals.

Alcohol Synthesis Using Carbon Dioxide

Hydroformylation (oxo reaction) is one of the key processes in the chemical industry to produce more than 10 million tons of chemicals every year. We have developed new hydro-formylation using CO2 as a reactant in place of toxic CO.

New Synthesis of Phosphorescent Materials for Organic Light-Emitting Diodes (OLEDs)

We studied microwave-assisted synthesis of tris-cyclometallated iridium(III) complexes as phos-phorescent materials for OLEDs. The iridium(III) complexes were obtained rapidly, selectively and efficiently using this new method.

Molecular Design of Soft-material-based Functional Probes as for Green Sustainable Chemistry

Calixarenes are a class of cyclo-oligomers formed via a phenol–formaldehyde condensation. We have demonstrated that calix[4]arene-based fluorogenic probes with boron-dypyrrin groups serve as an excellent fluorogenic probe for rare earth metal ions, especially Dy ion for the first time.

Molecular Robotics

Chemical reactions traditionally refer to the “collision probability” among molecules conditioned by thermodynamics. On the contrary, reactions in living beings are considered as “necessitated or inevitable outcome” rather than probability. The former position regards chemical reaction as phenomena explainable by molecular dynamics, while the latter ones are considered as proceeding by way of “recognition process”. It can be noted that “recognition process” is a key to develop the functionality of chemical reactions. We are also doing research of the sensing-processing-actuating functions at the molecular level through the project “Molecular Robotics” funded from MEXT.

Molecular Tweezers

Synthetic receptors possessing two complexing chromophores connected by a single spacer are referred to as molecular tweezers. The electrochemical behavior represents that 1,4-diazabicyclo[2.2.2]octane (DABCO) is released from the complex formed between calix[4]arene-bis-porphyrin conjugate and DABCO, just after cooperative two-oxidation occurs at 0.41 V.

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Members

Position Name Email(*)
Team Leader Ken-ichi Tominaga (D. Sci.) k-tominaga
Chief Senior Researcher Takashi Arimura (D. Eng.) takashi-arimura
Senior Researcher Hideo Konno (D. Eng.) h-konno
Senior Researcher Koji Nemoto (Ph. D.) k-nemoto
Researcher Kazunori Sasaki (Ph. D.) sasaki-kazu
Postdoctoral Researcher Atsushi Yamamoto (D. Sc.) atsushi.yamamoto

*Please add “@aist.go.jp” after each local part.

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Results

Publication List

Title Member Bibliographic data
Anti-inflammatory marine cyclic peptide stylissatin A and its derivatives inhibit differentiation of murine preadipocytes M. Zhang, T. Sunaba, Y. Sun, K. Sasaki, H. Isoda, H. Kigoshi, M. Kita Chem. Commun., 55, 5471 (2019)
3,4,5-Tricaffeoylquinic acid induces adult neurogenesis and improves deficit of learning and memory in aging model senescence-accelerated prone 8 mice K. Sasaki, J. Davies, N. G. Doldán, S. Arao, F. Ferdousi, F. G. Szele, H. Isoda Aging (Albany NY)., 11(2), 401-422 (2019)
Methoxy-substituted tetrakisquinoline analogs of EGTA and BAPTA for fluorescence detection of Cd2+ Y. Mikata, M. Kaneda, H. Konno, A. Matsumoto, S. Sato, M. Kawamura, S. Iwatsuki Dalton Trans., 48, 3840-3852 (2019)
Pyrophosphate-Induced Intramolecular Excimer Formation in Dinuclear Zinc(II) Complexes with Tetrakisquinoline Ligands Y. Mikata, R. Ohnishi, R. Nishijima, A. Matsumoto, H. Konno Inorg. Chem., 57, 7724-7734 (2018)
青色リン光材料の開発動向 今野 英雄, 高安 敏 有機ELに関する発光効率向上, 部材開発, 新しい用途展開, (株)技術情報協会, 第3節, p. 81-90 (2018), ISBN 978-4-86104-692-6.
Reverse water gas shift reaction using supported ionic liquid phase catalysts T. Yasuda, E. Uchiage, T. Fujitani, K. Tominaga, M. Nishida Applied Catalysis B, 232, 299-305 (2018)
Anisotropic celf-oscillating reaction in liquid crystalline nanosheet hydrogels M. Shintate, T. Inadomi, S. Yamamoto, Y. Kuboyama, Y. Ohseto, T. Arimura, T. Nakazumi, Y. Hara, N. Miyamoto J. Phys. Chem. B, 122, 2957-2961 (2018)
Favorskii-Type Rearrangement of the 4,5-Epoxymorphinan Skeleton N. Kutsumura, Y. Koyama, Y. Suzuki, K. Tominaga, N. Yamamoto, T. Saitoh, Y. Nagumo, H. Nagase Org. Lett., 20, 1559-1562 (2018)
Modulation of Neurogenesis through the Promotion of Energy Production Activity Is behind the Antidepressant-Like Effect of Colonial Green Alga, Botryococcus braunii. Front Physiol K. Sasaki, M. B. Othman, M. Demura, M. Watanabe, H. Isoda Aging (Albany NY)., 8: 900 (2017)
One-step Conversion of Levulinic Acid to Succinic Acid Using I2 /t-BuOK System: The Iodoform Reaction Revisited R. Kawasumi, S. Narita, K. Miyamoto, K. Tominaga, R. Takita, M. Uchiyama Scientific Reports, 7, 17967-17974 (2017)
TQOPEN (N,N,N’,N’-Tetrakis(2-quinolylmethyl)-3-oxa-1,5-pentanediamine) Family as Heptadentate Fluorescent Cd2+ Sensors Y. Mikata, A. Kizu, K. Nozaki, H. Konno, H. Ono, S. Mizutani, S. Sato Inorg. Chem., 56, 7404-7415 (2017)
A Reactor System Using Electrospray in the Liquid Phase and Its Application in Selective Cyclosiloxane Synthesis Y. Ido, H. Kobara, K. Tominaga, A. Wakisaka Ind. Eng. Chem. Res., 56(16), 4878-4882 (2017)
Electrochemically Switchable Molecular-Tweezers T. Arimura, J. Do, F. Tanaka Journal of Oleo Science, 66(4), 419-423 (2017)
Replacement of quinolines with isoquinolines affords target metal ion switching from Zn2+ to Cd2+ in the fluorescent sensor TQLN(N,N,N’,N’-tetrakis(2-quinolylmethyl)-2,6-bis(aminomethyl)pyridine) Y. Mikata, A. Takekoshi, M. Kaneda, H. Konno, K. Yasuda, M. Aoyama and S. Tamotsu Dalton Trans., 46, 632-637 (2017)
Levulinic acid Synthesis from Lignocellulosic Resources and its Future Perspective K. Nemoto and K. Tominaga, J. Jpn. Inst. Energy, 95, 515-520 (2016)
A Belousov-Zhabotinsky Oscillator Driven by a Water-Soluble MetalloPorphyrin M. Mukai, J. Do, N. Miyamoto, T. Arimura ChemistrySelect, 1(4), 877-878 (2016)
Neuroprotective effect of Picholine virgin olive oil and its hydroxycinnamic acids component against β-amyloid-induced toxicity in SH-SY5Y neurotypic cells. M. O. Villareal, K. Sasaki, D. Margout, C. Savry, Z. Almaksour, M. Larroque, H. Isoda Cytotechnology, 68(6), 2567-2578 (2016)
Fluorescent Detection of Phosphate lon via a Tetranuclear Zinc Complex Supported by a Tetrakisquinoline Ligand and μ4-PO4 Core Y. Mikata, R. Ohnishi, R. Nishijima, H. Konno Inorg. Chem., 55, 11440-11446 (2016)
Efficient nickel-catalyzed hydrocyanation of alkenes using acetone cyanohydrin as a safer cyano source K. Nemoto, T. Nagafuchi, K. Tominaga, K. Sato Tetrahedron Lett., 57, 3199 (2016)
A practical and efficient synthesis of methyl levulinate from cellulosic biomass catalyzed by an aluminum-based mixed acid catalyst system K. Tominaga, K. Nemoto, Y. Kamimura, A. Yamada, Y. Yamamoto, K. Sato RSC Adv., 6, 65119 (2016)
OFF-ON-OFF Fluorescent Response of N,N,N’,N’-Tetrakis(1-isoquinolylmethyl)-2-hydroxy-1,3-propanediamine (1-isoHTQHPN) toward Zn2+ Y. Mikata, R. Ohnishi, A. Ugai, H. Konno, Y. Nakata, I. Hamagami, S. Sato Dalton Trans., 45, 7250, (2016)

Cooperative In–Sn catalyst system for efficient methyl lactate synthesis from biomass-derived sugars

K. Nemoto, Y. Hirano, K. Hirata, T. Takahashi, H. Tsuneki, K. Tominaga, K. Sato App. Cat. B-Environ.,
183, 8, (2016)
OFF-ON, Ratiometric, and ON-OFF Fluorescent Responses of Thioether-Linked Bisquinolines toward Hg2+ and Fe3+ Ions Y. Mikata, K. Nakanishi, F. Nakagaki, A. Kizu, H. Konno Eur. J. Inorg. Chem., 22, 3769, (2015)
Tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA) as a highly fluorescent Zn2+ probe prepared by convenient C3-symmetric tripodal amine synthesis Y. Mikata, Y. Nodomi, R. Ohnishi, A. Kizu, H. Konno Dalton Trans., 44, 8021, (2015)
TQPHEN (N,N,N’,N’-tetrakis(2-quinolylmethyl)-1,2-phenylenediamine) derivatives as highly selective fluorescent probes for Cd2+ Y. Mikata, A. Kizu, H. Konno Dalton Trans., 44, 104, (2015)
Facile and Efficient Transformation of Lignocellulose into Levulinic Acid Using an AlCl3·6H2O/H3PO4 Hybrid Acid Catalyst K. Nemoto, K. Tominaga and K. Sato Bull. Chem. Soc. Jpn.,88, 1752, (2015)
Zinc-specific intramolecular excimer formation in TQEN derivatives: fluorescence and zinc binding property of TPEN-based hexadentate ligands Y. Mikata, S. Takeuchi, E. Higuchi, A. Ochi, H. Konno, K. Yanai, S. Sato Dalton Trans., 43, 16377, (2014)
Isoquinoline-derivatized tris(2-pyridylmethyl)amines as fluorescent zinc sensors with strict Zn2+/Cd2+ selectivity Y. Mikata, K. Kawata, S. Takeuchi, K. Nakanishi, H. Konno, S. Itami, K. Yasuda, S. Tamotsu and S. C. Burdette
Dalton Trans., 43, 10751, (2014)
Bis(2-quinolylmethyl)ethylenediaminediacetic acids (BQENDAs), TQEN-EDTA hybrid molecules as fluorescent zinc sensors Y. Mikata, S. Takeuchi, H. Konno, S. Iwatsuki, S. Akaji, I. Hamagami, M. Aoyama, K. Yasuda, S. Tamotsu and S. C. Burdette Dalton Trans., 43, 10013, (2014)
Straightforward Synthesis of Levulinic Acid Ester from Lignocellulosic Biomass Resources K. Nemoto, K. Tominaga and K. Sato Chem. Lett., 43, 1327, (2014)
バイオマス資源を活用した有機合成研究 根本耕司 ペトロテック, 37, 499, (2014)
8-TQEN (N, N, N′, N′-tetrakis(8-quinolylmethyl)ethylenediamine) analogs as fluorescent cadmium sensors: strategies to enhance Cd2+-induced fluorescence and Cd2+/Zn2+ selectivity Y. Mikata, A. Takekoshi, A. Kizu, Y. Nodomi, M. Aoyama, K. Yasuda, S. Tamotsu, H. Konno and S. C. Burdette RSC Adv., 4, 12849, (2014)
Quinoline-attached triazacyclononane(TACN) derivatives as fluorescent zinc sensors Y. Mikata, Y. Nodomi, A. Kizu and H. Konno Dalton Trans., 43, 1684, (2014)
Quantitative Fluorescent Detection of Pyrophosphate with Quinoline-Ligated Dinuclear Zinc Complexes Y. Mikata, A. Ugai, R. Ohnishi, H. Konno Inorg. Chem., 52, 10223-10225 (2013)
Reverse Water-Gas Shift Reaction Catalyzed by Mononuclear Ru Complexes K. Tsuchiya, J. -D. Huang, and K. Tominaga ACS Catal., 3, 2865, (2013)
触媒変換プロセスによるセルロース系バイオマスからの有用化学品合成 富永 健一 AIST Today, 13, 14, (2013)
触媒を使って植物から有用な化学品を作る 富永 健一 JIR常陽産研ニューズ, 278, 7, (2013)
Formation of η2-Coordinated Dihydropyridine–Ruthenium(II) Complexes by Hydride Transfer from Ruthenium(II) to Pyridinium Cations Y. Matsubara, T. Kosaka, K. Koga, A. Nagasawa, A. Kobayashi, H. Konno, C. Creutz, K. Sakamoto, and O. Ishitani Organometallics, 32, 6162, (2013)
有機EL青色燐光材料の分子設計 今野英雄、井戸洋平 月刊ディスプレイ, 19, 19 (2013)
Quinoline-based fluorescent zinc sensors with enhanced fluorescence intensity, Zn/Cd selectivity and metal binding affinity by conformational restriction Y. Mikata, Y. Sato, S. Takeuchi, Y. Koroda, H. Konno, S. Iwatsuki Dalton Trans., 42, 9688 (2013)
有機EL燐光材料の開発 今野英雄 J. Jpn. Soc. Color Mater., 85, 489 (2012)
Quinoline-Based, Glucose-Pendant Fluorescent Zinc Probes Y. Mikata, A. Ukai, K. Yasuda, S. Itami, T. Tamotsu, H. Konno, S. Iwatsuki Chem. Biodiv., 9, 2064 (2012)
有機EL燐光材料の製造法と開発動向 今野英雄 Mater. Stage, 11, 60 (2012)
有機EL青色燐光材料の開発動向 今野英雄 クリーンテクノロジー, 22, 49 (2012)
Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs) Y. Mikata, K. Kawada, S. Iwatsuki, H. Konno Inorg. Chem., 51, 1859 (2012)
Microwave-Assisted Synthesis of Metal Complexes T. Abe, T. Miyazawa, Y. Kawanishi, H. Konno Mini Rev. Org. Chem., 8, 315 (2011)
Mixed-acid systems for catalytic synthesis of methyl levulinate from cellulose K. Tominaga, A. Mori, Y. Fukushima, S. Shimada, K. Sato Green Chem., 13, 810 (2011)
Methoxyquinoline-diethylenetriamine conjugate as a fluorescent zinc sensor Y. Mikata, A. Yamashita, K. Kawada, H. Konno, S. Itami, K. Yasuda, T. Tamotsu Dalton Trans., 40, 4976 (2011)
Methoxy-substituted isoTQEN family for enhanced fluorescence response toward zinc ion Y. Mikata, A. Yamashita, K. Kawada, H. Konno, S. Itami, K. Yasuda, T. Tamotsu Dalton Trans., 40, 4059 (2011)
青色燐光材料 今野 英雄 有機EL照明用材料の開発と評価技術, サイエンス&テクノロジー(株), 第2章, 第1節, p. 11-20 (2010),ISBN 978-4-903413-92-1.
Development of an Efficient and Durable Photocatalytic System for Hydride Reduction of an NAD(P)+ Model Compound Using a Ruthenium(II) Complex Based on Mechanistic Studies Y. Matsubara, Y. Koga, A. Kobayashi, H. Konno, K. Sakamoto, I. Morimoto, O. Ishitani J. Am. Chem. Soc., 132, 10547 (2010)
Deuteration isotope effect on nonradiative transition of fac-tris (2-phenylpyridinato) iridium (III) complexes T. Abe, T. Miyazawa, H. Konno, Y. Kawanishi Chem. Phys. Lett., 491, 199 (2010)
An environmentally friendly hydroformylation using carbon dioxide as a reactant catalyzed by immobilized Ru-complex in ionic liquids K. Tominaga Catal Today, 115, 70 (2006)

Invited Lectures

Presentation Title Name of society Date Speaker
フェムトリアクターを用いた有機合成・高分子合成プロセスの可能性 JACI先端化学・材料技術部会講演会 2017.11 富永健一
The exploration research into medicinal functions of Aurantiochytrium and Botryococcus braunii using bioassay The 10th annual Algae Biomass Summit 2016.10 Hiroko Isoda, K. Sasaki, M. Sakamaki, S. Takahashi, M. Watanabe, M. Demura, M. Yoshida, H. Kigoshi, M. Kita, K. Tominaga
Cooperative acid catalyst systems for efficient synthesis of methyl levulinate from wood biomass International Symposium on Catalytic Conversion of Biomass 2016 2016.6 K. Tominaga, K. Nemoto, Y. Kamimura, A. Yamada, Y. Yamamoto, K. Sato
木質バイオマスの触媒変換によるバイオマスリファイナリー エコマテリアル研究会 2015.10 富永健一
循環型原料を用いた有用化学品合成のための触媒開発 第34回触媒学会若手会「夏の研修会」 2013.7 富永健一
バイオマス資源を用いた有用化学品合成のための有機合成戦略 理研バイオマス若手研究会 2013.6 根本耕司
レブリン酸を基幹物質とするバイオマスリファイナリー 触媒資源化協会講演会 2012.7 富永健一
有機EL素子と有機材料~りん光材料の製法開発~ 触媒資源化協会講演会 2012.7 今野英雄
レブリン酸を基幹物質とするバイオマスリファイナリー 三菱ガス化学株式会社講演会 2012.7 富永健一
有機ELリン光材料の開発 三菱ガス化学株式会社講演会 2012.9 今野英雄
有機EL燐光材料の製造方法と開発動向 株式会社技術情報協会セミナー 2011.12 今野英雄

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