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Assembling Methods of Functional Molecules for Development of Muti-modarity Molecular Probes

Research Project

Project/Area Number 26350971
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical biology
Research InstitutionTokyo Medical and Dental University

Principal Investigator

Yoshida Suguru  東京医科歯科大学, 生体材料工学研究所, 准教授 (10583750)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsケミカルバイオロジー / 有機化学 / 分子プローブ / アジド / クリック反応
Outline of Final Research Achievements

"Molecular probe" which is a multifunctional molecule for advancing life science research has attracted attention as an important tool. However, synthesis of multifunctional molecules such as multi-modality probes is not easy. We studied on multi-click chemistry to enable facile preparation of a variety of multi-functional molecules by sequential use of click reactions, which are widely used as a reliable method to conjugate two molecules. As the results, we successfully developed a method to transiently protect the clickability of cyclic alkyne moieties toward azides. This method enabled the synthesis of cyclic alkynes bearing a functional group from functional azides via a terminal alkyne-selective click reaction.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (46 results)

All 2017 2016 2015 2014

All Journal Article (21 results) (of which Peer Reviewed: 21 results,  Open Access: 11 results,  Acknowledgement Compliant: 21 results) Presentation (25 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results)

  • [Journal Article] Facile Synthesis of Phthalides from Methyl ortho-Iodobenzoates and Ketones via an Iodine-Magnesium Exchange Reaction Using a Silylmethyl Grignard Reagent2017

    • Author(s)
      Y. Nakamura, S. Yoshida, and T. Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 6 Pages: 858-861

    • DOI

      10.1246/cl.170211

    • NAID

      130005689308

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Enhancing the Synthetic Utility of 3-Haloaryne Intermediates by their EfficientGeneration from Readily Synthesizable ortho-Iodoaryl Triflate-type Precursors2017

    • Author(s)
      S. Yoshida, A. Nagai, K. Uchida, and T. Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 5 Pages: 733-736

    • DOI

      10.1246/cl.170136

    • NAID

      130005655718

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Three-Component Coupling of Triflyloxy-Substituted Benzocyclobutenones, Organolithium Reagents, and Arynophiles Promoted by Generation of Aryne via Carbon-Carbon Bond Cleavage2017

    • Author(s)
      K. Uchida, S. Yoshida, and T. Hosoya
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 5 Pages: 1184-1187

    • DOI

      10.1021/acs.orglett.7b00242

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Aromatic Azido-selective Reduction via the Staudinger Reaction Using Tri-n-butylphosphonium Tetrafluoroborate with Triethylamine2017

    • Author(s)
      T. Meguro, S. Yoshida, and T. Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 4 Pages: 473-476

    • DOI

      10.1246/cl.161159

    • NAID

      130005549122

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Facile Synthesis of Multisubstituted Benzo[b]furans via 2,3-Disubstituted 6,7-Furanobenzynes Generated from ortho-Iodoaryl Triflate-type Precursors2017

    • Author(s)
      T. Morita, Y. Nishiyama, S. Yoshida, and T. Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 1 Pages: 118-121

    • DOI

      10.1246/cl.160951

    • NAID

      130005308352

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Facile Diversification of Simple Benzo[b]thiophenes via Thienobenzyne Intermediates2017

    • Author(s)
      T. Morita, S. Yoshida, M. Kondo, T. Matsushita, and T. Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 1 Pages: 81-84

    • DOI

      10.1246/cl.160901

    • NAID

      130005308324

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Reactions of Arynes with Sulfoximines: Formal Sulfinylamination vs N-Arylation2017

    • Author(s)
      S. Yoshida, H. Nakajima, K. Uchida, T. Yano, M. Kondo, T. Matsushita, and T. Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 1 Pages: 77-80

    • DOI

      10.1246/cl.160865

    • NAID

      130005308348

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Aryne Relay Chemistry en Route to Aminoarenes: Synthesis of 3-Aminoaryne Precursors via Regioselective Silylamination of 3-(Triflyloxy)arynes2016

    • Author(s)
      S. Yoshida, Y. Nakamura, K. Uchida, Y. Hazama, and T. Hosoya
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 23 Pages: 6212-6215

    • DOI

      10.1021/acs.orglett.6b03304

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Thiazolobenzyne: a versatile intermediate for multisubstituted benzothiazoles2016

    • Author(s)
      S. Yoshida, T. Yano, Y. Nishiyama, Y. Misawa, M. Kondo, T. Matsushita, K. Igawa, K. Tomooka, and T. Hosoya
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 75 Pages: 11199-11202

    • DOI

      10.1039/c6cc05112j

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Controlled Generation of 3-Triflyloxyarynes2016

    • Author(s)
      K. Uchida, S. Yoshida, and T. Hosoya
    • Journal Title

      Synthesis

      Volume: 48 Issue: 23 Pages: 4099-4109

    • DOI

      10.1055/s-0035-1562532

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Single C-F Bond Cleavage of Trifluoromethylarenes with an ortho-Silyl Group2016

    • Author(s)
      S. Yoshida, K. Shimomori, Y. Kim, and T. Hosoya
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 35 Pages: 10406-10409

    • DOI

      10.1002/anie.201604776

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Diverse Benzotriazoles from Aryne Precursors Bearing an Azido Group via Inter- and Intramolecular Cycloadditions2016

    • Author(s)
      S. Yoshida, T. Morita, and T. Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 7 Pages: 726-728

    • DOI

      10.1246/cl.160349

    • NAID

      130005253015

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Generation of cycloheptynes and cyclooctynes via a sulfoxide–magnesium exchange reaction of readily synthesized 2-sulfinylcycloalkenyl triflates2015

    • Author(s)
      Yoshida, S., Karaki, F., Uchida, K., Hosoya, T.
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 42 Pages: 8745-8748

    • DOI

      10.1039/c5cc01784j

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An Alternative Method for Generating Arynes from ortho-Silylaryl Triflates: Activation by Cesium Carbonate in the Presence of a Crown Ether2015

    • Author(s)
      Suguru Yoshida, Yuki Hazama, Yuto Sumida, Takahisa Yano, Takamitsu Hosoya
    • Journal Title

      Molecules

      Volume: 20 Issue: 6 Pages: 10131-10140

    • DOI

      10.3390/molecules200610131

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Facile Synthesis of Diverse Multisubstituted ortho-Silylaryl Triflates via C-H Borylation2015

    • Author(s)
      Suguru Yoshida, Ken Shimomori, Takako Nonaka, Takamitsu Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 10 Pages: 1324-1326

    • DOI

      10.1246/cl.150535

    • NAID

      130005101452

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Concise Synthesis of v‐Coelenterazines2015

    • Author(s)
      Takamitsu Hosoya, Rie Iimori, Suguru Yoshida, Yuto Sumida, Yuiko Sahara-Miura, Jun-ichi Sato, Satoshi Inouye
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 15 Pages: 3888-3891

    • DOI

      10.1021/acs.orglett.5b01872

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] A mild and facile synthesis of aryl and alkenyl sulfides via copper-catalyzed deborylthiolation of organoborons with thiosulfonates2015

    • Author(s)
      Suguru Yoshida, Yasuyuki Sugimura, Yuki Hazama, Yoshitake Nishiyama, Takahisa Yano, Shigeomi Shimizu, Takamitsu Hosoya
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 93 Pages: 16613-16616

    • DOI

      10.1039/c5cc07463k

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct Thioamination of Arynes via Reaction with Sulfilimines and Migratory N‐Arylation2015

    • Author(s)
      Suguru Yoshida, Takahisa Yano, Yoshihiro Misawa, Yasuyuki Sugimura, Kazunobu Igawa, Shigeomi Shimizu, Katsuhiko Tomooka, Takamitsu Hosoya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 44 Pages: 14071-14074

    • DOI

      10.1021/jacs.5b10557

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Generation of Arynes Using Trimethylsilylmethyl Grignard Reagent for Activation of ortho-Iodoaryl or ortho-Sulfinylaryl Triflates2015

    • Author(s)
      Suguru Yoshida, Keisuke Uchida, Takamitsu Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 5 Pages: 691-693

    • DOI

      10.1246/cl.150060

    • NAID

      130005067968

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Transient Protection of Strained Alkynes from Click Reaction via Complexation with Copper2014

    • Author(s)
      Suguru Yoshida, Yasutomo Hatakeyama, Kohei Johmoto, Hidehiro Uekusa, Takamitsu Hosoya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 39 Pages: 13590-13593

    • DOI

      10.1021/ja507660x

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An efficient generation method and remarkable reactivities of 3-triflyloxybenzyne2014

    • Author(s)
      Suguru Yoshida, Keisuke Uchida, Kazunobu Igawa, Katsuhiko Tomooka, Takamitsu Hosoya
    • Journal Title

      Chemical Communications

      Volume: 50 Issue: 95 Pages: 15059-15062

    • DOI

      10.1039/c4cc07058e

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] ジアジドプローブ法のための分子連結法の開発2017

    • Author(s)
      吉田 優
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学川内北キャンパス、仙台国際センター(宮城県仙台市)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 3-(トリフリルオキシ)アラインを利用する多置換ベンゼン類のモジュラー合成法の開発2017

    • Author(s)
      吉田 優、中村 悠、内田圭祐、宮田敬大、陌間由貴、細谷孝充
    • Organizer
      日本薬学会第137年会(仙台)
    • Place of Presentation
      東北大学川内北キャンパス、仙台国際センター(宮城県仙台市)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] 高活性化学種の反応性制御にもとづく分子連結法の開発2017

    • Author(s)
      吉田 優
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] トリチルカチオンと求核剤とを一体型にした新反応剤を用いるトリフルオロメチル基の選択的官能基化反応の開発2016

    • Author(s)
      Kim Youngchan、下森 顕、細谷孝充、吉田 優
    • Organizer
      第110回有機合成シンポジウム
    • Place of Presentation
      早稲田大学早稲田キャンパス 国際会議場(東京都新宿区)
    • Year and Date
      2016-11-11
    • Related Report
      2016 Annual Research Report
  • [Presentation] 3-アミノアライン:前駆体の簡便合成法の開発と多彩な含窒素化合物の合成への展開2016

    • Author(s)
      中村 悠、内田圭祐、陌間由貴、吉田 優、細谷孝充
    • Organizer
      第110回有機合成シンポジウム
    • Place of Presentation
      早稲田大学早稲田キャンパス 国際会議場(東京都新宿区)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Annual Research Report
  • [Presentation] トリフルオロメチル基のC-F結合の選択的官能基化を可能にする新反応剤の開発2016

    • Author(s)
      Kim Youngchan、下森 顕、細谷孝充、吉田 優
    • Organizer
      第39回フッ素化学討論会
    • Place of Presentation
      アバンセ(佐賀県立男女共同参画センター・佐賀県立生涯学習センター)(佐賀県佐賀市)
    • Year and Date
      2016-09-29
    • Related Report
      2016 Annual Research Report
  • [Presentation] トリフリルオキシ基を脱離基として利用した炭素ー炭素結合切断を経るアライン発生法の開発2016

    • Author(s)
      内田圭祐、吉田 優、細谷孝充
    • Organizer
      第39回フッ素化学討論会
    • Place of Presentation
      アバンセ(佐賀県立男女共同参画センター・佐賀県立生涯学習センター)(佐賀県佐賀市)
    • Year and Date
      2016-09-29
    • Related Report
      2016 Annual Research Report
  • [Presentation] 複数のアジド基を有するチオフェン-S,S-ジオキシドを用いた多成分集積法の開発2016

    • Author(s)
      目黒友啓、吉田 優、細谷孝充
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢歌劇座(石川県金沢市)
    • Year and Date
      2016-09-27
    • Related Report
      2016 Annual Research Report
  • [Presentation] アラインのチオアミノ化反応を利用したフェノチアジン類の簡便合成法の開発2016

    • Author(s)
      松澤 翼、内田圭祐、吉田 優、細谷孝充
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢歌劇座(石川県金沢市)
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒を用いるチオスルホナートと有機ボロン酸類からの芳香族スルフィド類の無臭合成法の開発2016

    • Author(s)
      金本和也、杉村康行、吉田 優、細谷孝充
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学西早稲田キャンパス(東京都新宿区)
    • Year and Date
      2016-09-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 銅ー環状アルキン錯体を利用した分子連結法の開発2016

    • Author(s)
      吉田 優、畠山泰朋、喜井 勲、牧尾直明、栗原ともこ、伊藤晴海、唐木文霞、上本紘平、植草秀裕、井川和宣、友岡克彦、渡辺恭良、細谷孝充
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      早稲田大学西早稲田キャンパス(東京都新宿区)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] アラインのチオアミノ化を経由する多置換フェノチアジン類の簡便合成法の開発2016

    • Author(s)
      松澤 翼、内田圭祐、吉田 優、細谷孝充
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      ヒルトンニセコビレッジ(北海道虻田郡ニセコ町)
    • Year and Date
      2016-09-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] トリチルカチオンと求核剤を一体型にした新反応剤を用いるトリフルオロメチル基の選択的官能基化反応の開発2016

    • Author(s)
      Kim Youngchan、下森 顕、吉田 優、細谷孝充
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      ヒルトンニセコビレッジ(北海道虻田郡ニセコ町)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] オキサジアジノンの反応性を利用した分子連結手法の開発2016

    • Author(s)
      陳 勝男、目黒友啓、吉田 優、細谷孝充
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      ヒルトンニセコビレッジ(北海道虻田郡ニセコ町)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
  • [Presentation] オキサジアジノンの反応性を活かした新たな分子連結法の開発2016

    • Author(s)
      陳 勝男、目黒友啓、吉田 優、細谷孝充
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場(広島県広島市)
    • Year and Date
      2016-09-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] ハロゲン-マグネシウム交換反応を鍵とするヘテロアラインの新規発生法の開発と多置換複素環化合物の合成への応用2016

    • Author(s)
      森田隆太、吉田 優、細谷孝充
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場(広島県広島市)
    • Year and Date
      2016-09-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] 分子連結部位を有する環状アルキン-銅錯体の開発2016

    • Author(s)
      牧尾直明、畠山泰朋、井川和宣、友岡克彦、吉田 優、細谷孝充
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場(広島県広島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] Trimethylsilylmethyl Grignard Reagent: a Mild Activator Triggering Efficient Generation of Arynes from Various ortho-Iodoaryl Triflates2016

    • Author(s)
      Yoshida S, Shimomori K, Kim Youngchan, Hosoya T
    • Organizer
      11th International Symposiumu on Carbanion Chemistry (ISCC-11)
    • Place of Presentation
      Rouen, France
    • Year and Date
      2016-07-20
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新しいマルチアジド化合物をプラットフォーム分子として用いる機能性分子集積法の開発2016

    • Author(s)
      吉田 優・三澤善大・栗原ともこ・森田隆太・喜井 勲・渡辺恭良・細谷孝充
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] Transient Protection of strained alkynes from click reaction via complexation with copper.2015

    • Author(s)
      Yoshida S, Hatakeyama Y, Johmoto K, Uekusa H, Hosoya T.
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, Hawaii, USA)
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Generation of arynes and cycloalkynes via a sulfoxide-magnesium exchange reaction of readily synthesized precursors.2015

    • Author(s)
      Yoshida S, Uchida K, Karaki F, Hosoya T.
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, Hawaii, USA)
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Selective C-F Bond Cleavage via a Silylium Intermediate.2015

    • Author(s)
      Yoshida S, Shimomori K, Kim Y, Hosoya T.
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Rihga Royal Hotel Kyoto (Kyoto,JAPAN)
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 高活性化学種の反応性制御にもとづく分子連結法の開発2015

    • Author(s)
      吉田 優
    • Organizer
      第50回天然物化学談話会
    • Place of Presentation
      グリーンピア岩沼モンタナリゾート(宮城県岩沼市)
    • Year and Date
      2015-07-02
    • Related Report
      2015 Research-status Report
  • [Presentation] アラインのMichaelis-Arbuzov型反応による多置換芳香族リン化合物合成法の開発2015

    • Author(s)
      吉田優、塚本史雄、下森 顕、細谷孝充
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 官能基の「歪み」に着目した分子連結法の開発2015

    • Author(s)
      吉田優
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
    • Invited

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Published: 2014-04-04   Modified: 2018-03-22  

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