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Synthesis of linear and branched oligomers with the coupling reaction of heteroaromatic compounds

Research Project

Project/Area Number 25288049
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionKobe University

Principal Investigator

Mori Atsunori  神戸大学, 工学(系)研究科(研究院), 教授 (90210111)

Co-Investigator(Renkei-kenkyūsha) UEDA Yasukiyo  神戸大学, 大学院・工学研究科, 教授 (40116190)
SUGIE Atsushi  神戸大学, 大学院・工学研究科, 助教 (80605907)
Project Period (FY) 2013-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥18,330,000 (Direct Cost: ¥14,100,000、Indirect Cost: ¥4,230,000)
Fiscal Year 2016: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2015: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2014: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2013: ¥7,800,000 (Direct Cost: ¥6,000,000、Indirect Cost: ¥1,800,000)
Keywordsヘテロ芳香族化合物 / 分岐状オリゴマー / 鎖状オリゴマー / C-Hカップリング / 遷移金属触媒 / ヘテロ芳香族 / オリゴチオフェン / ポリチオフェン / カップリング反応 / チオフェン / チエニレンビニレン / 溝呂木-Heck型反応 / C-Hカップリング / チエニレン-ビニレン / N-ヘテロ環状カルベン / シロキサン結合 / デンドリマー / ニッケル触媒 / 色素増感太陽電池 / カルバゾール / シアノアクリル酸 / 有機色素 / CHカップリング / 分岐状チオフェン / 太陽電池
Outline of Final Research Achievements

Linear and branched heteroaromatic oligomers were synthesized using C-H coupling reactions catalyzed by transition metal complexes, in which tolerance of various functional groups were studied. Further functional group transformation reactions were developed to undergo additional extension of the heteroaromatic unit. Disiloxane moieties was successfully introduced into olikgothiophenes to improve solubilities towared organic solvents. Water-soluble group was also examined to introduce as a functional group. Heteroaromatic oligomers bearing vinylene spacer were also prepared.

Report

(5 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (48 results)

All 2017 2016 2015 2014 2013 Other

All Journal Article (20 results) (of which Peer Reviewed: 20 results,  Acknowledgement Compliant: 9 results) Presentation (24 results) (of which Invited: 5 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Remarkable Reactivity Difference of Chlorothiophene vs. Chlorinated Oligothiophenes in the NiCl2(PPh3)2-Catalyzed Polymerization2017

    • Author(s)
      中川 尚希,小倉 忠之,藤田 佳祐,炭野 有吾,橋本 亨昌,岡野 健太郎,森 敦紀
    • Journal Title

      Chem. Lett.

      Volume: 46 Issue: 4 Pages: 453-455

    • DOI

      10.1246/cl.161180

    • NAID

      130005549099

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Step-Efficient Pathway to Chlorine-Functionalized Thiophene Oligomers by Palladium-Catalyzed Deprotonative Coupling of Chlorothiophenes2017

    • Author(s)
      藤田 佳祐,中川 尚希,砂原 一潤,小倉 忠之,岡野 健太郎,森 敦紀
    • Journal Title

      Synthesis

      Volume: 49 Issue: 06 Pages: 1285-1294

    • DOI

      10.1055/s-0036-1588094

    • NAID

      120006220755

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Poly(3-substituted thiophene)s of Remarkably High Solubility in Hydrocarbon via Nickel-Catalyzed Deprotonative Cross-Coupling Polycondensation2016

    • Author(s)
      3.Fujita, K.; Sumino, Y.; Ide, K.; Tamba, S.; Shono, K.; Shen, J.; Nishino, T.; Mori, A.*; Yasuda, T.
    • Journal Title

      Macromolecules

      Volume: 49 Issue: 4 Pages: 1259-1269

    • DOI

      10.1021/acs.macromol.5b02524

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Oligo(thienylene-vinylene) by Regiocontrolled Deprotonative Cross Coupling2016

    • Author(s)
      Shota Tanaka, Yuta Fukui, Naoki Nakagawa, Kohei Murakami, Takurou N. Murakami, Nagatoshi Koumura, Atsunori Mori
    • Journal Title

      Organic Letters

      Volume: 2016 Issue: 4 Pages: 650-653

    • DOI

      10.1021/acs.orglett.5b03567

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Furan-Oxazole Conjugated Fluorescent Materials from Biomass-Derived Furfural through Cross-Coupling Reactions2016

    • Author(s)
      Y. Murase, K. Ashida, S. Tanaka, K. Okano, A. Mori
    • Journal Title

      Heterocycles

      Volume: 93 Issue: 1 Pages: 140-140

    • DOI

      10.3987/com-15-s(t)9

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Linear-selective Cross-coupling Polymerization of Branched Oligothiophene by Deprotonative Metalation and Cross-coupling2015

    • Author(s)
      Kohei Murakami, Shota Tanaka, Atsunori Mori
    • Journal Title

      Polymer Chem/

      Volume: 6 Issue: 36 Pages: 6573-6578

    • DOI

      10.1039/c5py00945f

    • NAID

      120006220765

    • Related Report
      2016 Annual Research Report 2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Addition-Elimination of Aryldimethylaluminum to Vinylarenes Promoted by the Addition of Ketone2015

    • Author(s)
      Kazuki Itami, Shota Tanaka, Kazuhiro Sunahara, Go Tatsuta, Atsunori Mori
    • Journal Title

      Asian J. Org. Chem.

      Volume: 6 Pages: 6573-6578

    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Enantioselective Synthesis of Macrocyclic Heterobiaryl Derivatives of Molecular Asymmetry by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis2015

    • Author(s)
      Yoichi Okayama, Satoru Tsuji, Yuka Toyomori, Atsunori Mori, Sachie Arae, Wei-Yi Wu, Tamotsu Takahashi, Masamichi Ogasawara
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 54

    • NAID

      120006220759

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ethylaluminum as an ethylene source for the Mizoroki-Heck-type reaction. Rhodium-catalyzed preparation of stilbene derivatives2015

    • Author(s)
      Shota Tanaka, Kazuki Itami, Kazuhiro Sunahara, Go Tatsuta, Atsunori Mori
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 10 Pages: 1949-1952

    • DOI

      10.1039/c4cc09306b

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed α-Arylation of Carboxylic Acid Derivatives with Grignard Reagent2014

    • Author(s)
      Daiki Tanaka, Shota Tanaka, Atsunori Mori
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2014 Issue: 20 Pages: 4254-4257

    • DOI

      10.1002/ejoc.201402450

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Polythiophene synthesis via halogen dance2014

    • Author(s)
      Keisuke Shono, Yugo Sumino, Shota Tanaka, Shunsuke Tamba, Atsunori Mori
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 1 Issue: 6 Pages: 678-682

    • DOI

      10.1039/c4qo00109e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Studies on the effect of N-heterocyclic carbene as a ligand for nickel(II)-catalyzed polymerization of thiophenes2014

    • Author(s)
      Atsunori Mori, Makoto Fujio, Shunsuke Tamba
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 1 Pages: 617-617

    • DOI

      10.3987/com-14-s(k)11

    • NAID

      120006220734

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and properties of regioregular poly (3-substituted thiophene) bearing disiloxane moiety in the substituent. Remarkably high solubility in hexane.2014

    • Author(s)
      Atsunori Mori, Kenji Ide, Shunsuke Tamba, Satoru Tsuji, Yuka Toyomori, Takeshi Yasuda.
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 5 Pages: 640-642

    • DOI

      10.1246/cl.131222

    • NAID

      130004868129

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel(II)-Catalyzed Cross-Coupling Pelycondensation of Thiophones via C-S Bond Cleavage2014

    • Author(s)
      Shunsuke Tamba, Kanta Fuji, Karin Nakamura, Atsunori Mori
    • Journal Title

      Organometallics

      Volume: 33 Issue: 1 Pages: 12-15

    • DOI

      10.1021/om4010737

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Introduction of Heteroarene Functionality on the Bipedal-Thiol-Capped Gold Nanoparticle by Deprotonative C-H Coupling with Palladium Complex2014

    • Author(s)
      Atsuahi Sugie, Hiroki Yamauchi, Kei, Miyamura, Kenta Kumazawa, Shota Tanaka, Kiyoshi Kanie, Atsushi Muramatsu, Atsunori Mori
    • Journal Title

      Heterocycles

      Volume: Vol 88, No.1 Issue: 1 Pages: 213-221

    • DOI

      10.3987/com-13-s(s)1

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Cross-Coupling of Vinylarenes with Arylaluminum Reagents in the Presence of Ketones2014

    • Author(s)
      Shota Tanaka, Atsunori Mori
    • Journal Title

      European Journal of Organic Chemistry

      Volume: Vbl.2014,Issue6 Issue: 6 Pages: 1167-1171

    • DOI

      10.1002/ejoc.201301757

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Murahashi Coupling Polymerization : Nickel(II)-N-Hererocyclic Carbene Complex-Catalyzed Polycondensation of Organolithium Species of (Hetero) arenes2013

    • Author(s)
      Kanta Fuii, Shunsuke Tamba, Keisuke Shono, Atsushi Sugie, Atsunori Mori
    • Journal Title

      Journal of the American Chemical Society

      Volume: 135 Issue: 33 Pages: 12208-12211

    • DOI

      10.1021/ja406374t

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile Preparation of Poly(3-Substituted Thiophene) Block Copolymers by Nickel-catalyzed Deprotonative Polycondensation without External Generation of Thiophene Organometallic Species2013

    • Author(s)
      Karin Nakamura, Shunsuke Tamba, Atsushi Sugie, Atsunori Mori
    • Journal Title

      Chemistry Letters

      Volume: 40 Issue: 10 Pages: 1200-1202

    • DOI

      10.1246/cl.130523

    • NAID

      10031201309

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Deprotonative metalation of chlorothiophene with Grignard reagent and catalytic cis-2, 6-dimethylpiperidine under mild conditions2013

    • Author(s)
      Shunsuke Tamba. Kenji Ide, Keisuke Shono, Atsushi Sugie, Atsunori Mori
    • Journal Title

      Synlett

      Volume: (印刷中)(掲載確定) Issue: 09 Pages: 1133-1136

    • DOI

      10.1055/s-0033-1338385

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Studies on the preference of multiple coupling in the introduction of thiophene ring into poly-halogenated aromatic compounds with nickel NHC catalyst2013

    • Author(s)
      Shota Tanaka
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 15 Pages: 1976-1979

    • DOI

      10.1016/j.tetlet.2013.01.127

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] 閉環メタセシス反応を用いないつるまき状分子不斉を有する新規大環状へテロアリールの合成2017

    • Author(s)
      芦田 汐未,田中 直樹,岡野 健太郎,森 敦紀
    • 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
  • [Presentation] 縮合反応を経由する非対称型つるまき状分子不斉化合物の合成2017

    • Author(s)
      井上 僚,松岡 大地,丸橋 和希,芦田 汐未,岡野 健太郎,森 敦紀
    • 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
  • [Presentation] ベンゾオキサゾールを配向基とするブロモフランのハロゲンダンス2017

    • Author(s)
      宮川 直樹,村瀬 右樹,岡野 健太郎,森 敦紀
    • 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
  • [Presentation] つる巻き状分子不斉の創出2016

    • Author(s)
      森 敦紀
    • Organizer
      平成28年度有機合成化学北陸セミナー
    • Place of Presentation
      石川県青少年総合研修センター(石川県・金沢市)
    • Year and Date
      2016-10-07
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Heterobiaryl with winding-vine-shaped molecular asymmetry2016

    • Author(s)
      森 敦紀
    • Organizer
      INTERNATIONAL SYMPOSIUM ON PURE & APPLIED CHEMISTRY (ISPAC) 2016
    • Place of Presentation
      クチン(マレーシア)
    • Year and Date
      2016-08-15
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 炭素-塩素結合をもつチオフェン誘導体のC-H結合におけるカップリング反応によるチオフェン-チオフェン結合の生成2016

    • Author(s)
      藤田佳佑・中川直希・砂原一潤・岡野健太郎・森敦紀
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府,京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] チオフェン誘導体のC-Hカップリング重合におけるモノマー構造多様性の検討2016

    • Author(s)
      中川直希・小倉忠之・藤田佳佑・炭野有吾・福井祐太・田中将太・岡野健太郎・森敦紀
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府,京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] チオフェン誘導体のC-Hカップリング重合における配位子効果の検討2016

    • Author(s)
      小倉忠之・中川直希・藤尾慎・橋本享昌・岡野健太郎・森敦紀
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府,京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 側鎖にジシロキサン結合を有する高脂溶性ポリチオフェンの合成2015

    • Author(s)
      炭野有吾・井手賢治・藤田佳佑・森 敦紀
    • Organizer
      第61回高分子研究発表会(神戸)
    • Place of Presentation
      神戸県民会館(兵庫県,神戸市)
    • Year and Date
      2015-07-17
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development on the Preparative Method for Oligothiophenes and Polythiophenes with Well-defined Structures2014

    • Author(s)
      Atsunori Mori
    • Organizer
      Vietnam-Malaysia International Chemical Congress
    • Place of Presentation
      ベトナム,ハノイ
    • Year and Date
      2014-11-07 – 2014-11-09
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] アリールアルミニウムのビニルアレーンへの溝呂木-Heck型付加脱離反応2014

    • Author(s)
      伊丹一起・田中将太・砂原一潤・立田 豪・森 敦紀
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Head to tail型チエニレン-ビニレンオリゴマーの精密合成2014

    • Author(s)
      福井祐太・田中将太・中川直希・森 敦紀
    • Organizer
      福井祐太・田中将太・中川直希・森 敦紀
    • Place of Presentation
      東北大学
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] ニッケル触媒を用いたポリチオフェン合成におけるN-ヘテロ環状カルベン(NHC)配位子効果の検討2014

    • Author(s)
      村上航平・森 敦紀
    • Organizer
      有機合成若手セミナー
    • Place of Presentation
      大阪大学
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] ハロゲンダンスを利用したポリチオフェン合成法2014

    • Author(s)
      炭野有吾,庄野圭亮,田中将太,丹波俊輔,森 敦紀
    • Organizer
      第60回高分子研究発表会(神戸)
    • Place of Presentation
      神戸市
    • Year and Date
      2014-07-24 – 2014-07-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] フルフラールを用いたπ共役系が拡張し たヘテロ芳香族化合物の合成2014

    • Author(s)
      立田 豪・田中将太・杉江敦司・森 敦紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 3 位置換基にジシロキサン結合を有する head-to-tail 型ポリチオフェンの 合成と性質2014

    • Author(s)
      豊森佑夏・井手賢治・丹波俊輔・辻 悟・森 敦紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 位置選択的なCーHカップリングを用いる 構造が明確に制御されたチエニレン-ビ ニレンオリゴマーの新規合成法2014

    • Author(s)
      福井 祐太・田中 将太・森 敦紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] オリゴチオフェンデンドリマーをモノマ ーとして用いる直鎖状高分子の合成2014

    • Author(s)
      村上航平,田中将太,森 敦紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ロジウム触媒を用いたアリールアルミニ ウムのビニルアレーンへの付加脱離反応2014

    • Author(s)
      田中 将太・伊丹 一起・立田 豪・森 敦紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ヘテロ芳香族の触媒的C-Hカップリング :チオフェン系有機材料,高分子材料の実用的合成法をめざして2014

    • Author(s)
      森 敦紀
    • Organizer
      有機合成化学協会関西支部2月セミナー
    • Place of Presentation
      大阪科学技術センター
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 触媒的C-Hカップリング反応を活用する有機合成,高分子合成2014

    • Author(s)
      森 敦紀
    • Organizer
      有機合成化学協会後期(秋季)有機合成講習会
    • Place of Presentation
      日本薬学会長井記念館
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Rhodium-Catalyzed Mizoroki-Heck Reaction of Arylaluminum with Vinylarene2013

    • Author(s)
      Shota Tanaka, Atsunori Mori
    • Organizer
      第10回カルボアニオン化学国際会議
    • Place of Presentation
      同志社大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] パラジウム触媒を用いるα-アリールカルボン酸とハロゲン化アリールとのクロスカップリング反応2013

    • Author(s)
      田中大貴,田中将太,杉江敦司,森 敦紀
    • Organizer
      有機金属討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Iterative synthesis of well-defined linear and branched oligothiophenes by nickel-catalyzed regioselective cross coupling2013

    • Author(s)
      Shota Tanaka, Daiki Tanaka, Go Tatsuta, Kohei Murakami, Shunsuke Tamba, Atsushi Sugie, Atsunori Mori
    • Organizer
      The 17th International Conference of Organometallic Chemistry Directed for Organic Synthesis
    • Place of Presentation
      Colorado State University (アメリカ)
    • Related Report
      2013 Annual Research Report
  • [Remarks] 研究の概要

    • URL

      http://seesaawiki.jp/w/moriorg3/d/Topics?wiki_id=45657

    • Related Report
      2016 Annual Research Report
  • [Remarks] 研究トピックス

    • URL

      http://seesaawiki.jp/w/moriorg3/d/Topics?wiki_id=45657

    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] フランオリゴマーポリエステルおよびその前駆体2017

    • Inventor(s)
      森 敦紀,宮川 直樹,岡野 健太郎,松本 拓也
    • Industrial Property Rights Holder
      森 敦紀,宮川 直樹,岡野 健太郎,松本 拓也
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017-03-10
    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] 五員ヘテロアリーレン-ビニレンポリマーの製造方法2015

    • Inventor(s)
      森 敦紀
    • Industrial Property Rights Holder
      森 敦紀
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-001160
    • Filing Date
      2015-01-30
    • Related Report
      2014 Annual Research Report

URL: 

Published: 2013-05-21   Modified: 2019-07-29  

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