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Research for fused aromatic molecules potential for super- and semi-conductors prepared by the photosensitizing condensation method

Research Project

Project/Area Number 23350059
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionGunma University

Principal Investigator

YAMAJI Minoru  群馬大学, 理工学研究院, 准教授 (20220361)

Co-Investigator(Kenkyū-buntansha) OKAMOTO Hideki  岡山大学, 自然科学研究科, 准教授 (30204043)
KUBOZONO Yoshihiro  岡山大学, 自然科学研究科, 教授 (80221935)
Project Period (FY) 2011-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥19,110,000 (Direct Cost: ¥14,700,000、Indirect Cost: ¥4,410,000)
Fiscal Year 2013: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2012: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2011: ¥11,180,000 (Direct Cost: ¥8,600,000、Indirect Cost: ¥2,580,000)
Keywords分子素子 / 光縮環反応 / 有機半導体 / 有機超伝導体 / 蛍光分子 / 電荷移動度 / 有機超伝導 / 有機光化学 / グラフェン / 有機超伝導材料・素子 / 太陽光増感色素 / 有機超伝導性 / 有機半導体性 / 光増感縮環法 / ピセン / フェナセン / 三重項吸収 / 電界効果トランジスタ / フルミネン
Research Abstract

Chemical formation of fused aromatic compounds requires a variety of steps and efforts. We have found a new method for synthesizing pure condensed aromatic compounds by UV light irradiation in solution. With this method, we have prepared polyaromatic fuzed compounds and five-membered aromatic compounds containing oxygen, nitrogen and sulfur atoms. Photophysical and photochemical properties of these compounds have been revealed for utilizing them as efficient luminescent materials. For the aim of applying them to electronic materials such as an electron transfer layer in field-effect transistors (FET), the electron mobility was measured. The photochemical mechanism of the photocondensation method was investigated by using laser flash photolysis techniques.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (54 results)

All 2014 2013 2012 2011 Other

All Journal Article (28 results) (of which Peer Reviewed: 28 results) Presentation (19 results) (of which Invited: 2 results) Remarks (3 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Efficient Synthetic Photocyclization for Phenacenes Using a Continuous Flow Reactor2014

    • Author(s)
      H. Okamoto, T. Takane, S. Gohda, Y. Kubozono, K. Sato, M. Yamaji, and K. Satake
    • Journal Title

      Chem. Lett.,

      Volume: 59 Issue: 7 Pages: 994-996

    • DOI

      10.1246/cl.140182

    • NAID

      130004868234

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two-Photon Chemistry from Upper Triplet States of Thymine2013

    • Author(s)
      V. Vendrell-Criado, G. M. Rodriguez-Muniz, M. Yamaji, V. Lhiaubet-Vallet, M. C. Cuquerella and M. A. Miranda
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 Pages: 16714-16719

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] S2 Fluorescence from picene vapor2013

    • Author(s)
      T. Itoh, M. Yamaji and H. Okamoto
    • Journal Title

      Chem. Phys. Lett

      Volume: 570 Pages: 26-28

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Photothermal Tautomerization of a UV Sunscreen (4-tert-Butyl-4 ′-methoxydibenzoylmethane) in Acetonitrile Studied by Steady-State and Laser Flash Photolysis2013

    • Author(s)
      M. Yamaji and M. Kida
    • Journal Title

      J. Phys. Chem. A

      Volume: 117 Pages: 1946-1951

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Emission and transient absorption measurements of substitution effects of C-C triple bonds on relaxation processes of the fluorescent state of naphthalenes2013

    • Author(s)
      M. Yamaji, H. Maeda, K. Minamida, T. Maeda, K. Asai, G.-I. Konishi and K. Mizuno
    • Journal Title

      Res. Chem. Intermed.

      Volume: 39 Pages: 321-345

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photochemical behaviors of a tethered 1,3-diketone derivative studied by transient absorption and time-resolved EPR measurements2013

    • Author(s)
      A. Kobayashi, M. Yamaji, S. Nakajima, K. Akiyama, S. Tero-Kubota, S. Kato and Y. Nakamura
    • Journal Title

      Chem. Phys. Lett.

      Volume: 555 Pages: 101-105

    • Related Report
      2013 Annual Research Report 2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] S2 fluorescence from picene vapor2013

    • Author(s)
      T. Itoh, M. Yamaji and H. Okamoto
    • Journal Title

      Chem. Phys. Lett.

      Volume: 570 Pages: 26-28

    • Related Report
      2013 Annual Research Report 2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 5-[4-(Dimethylamino)phenyl]-2-benzamidopyraz ines : fluorescent dyes based on Cypridina oxyluciferin2013

    • Author(s)
      T. Hirano, T. Nakagawa, A. Kodaka, S. Maki, H. Niwa and M. Yamaji
    • Journal Title

      Res. Chem. Intermed

      Volume: 39 Pages: 233-245

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Photochemical synthesis and electronic spectra of fulminene ([6]phenacene)2013

    • Author(s)
      H. Okamoto, M. Yamaji, S. Gohda, K. Sato, H. Sugino and K. Satake
    • Journal Title

      Res. Chem. Intermed.

      Volume: 39 Pages: 147-159

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two-Photon Chemistry from Upper Triplet States of Thymine2013

    • Author(s)
      V. Vendrell-Criado, G. M. Rodriguez-Muniz, M. Yamaji, V. Lhiaubet-Vallet, M. C. Cuquerella and M. A. Miranda
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 44 Pages: 16714-16719

    • DOI

      10.1021/ja408997j

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photo-Thermal Tautomerization of a UV-Sunscreen (4-tert-Butyl-4’-Methoxydibenzoylmethane) in Acetonitrile Studied by Steady-State and Laser Flash Photolysis2013

    • Author(s)
      M. Yamaji and M. Kida
    • Journal Title

      J. Phys. Chem. A

      Volume: 117 Issue: 9 Pages: 1946-1951

    • DOI

      10.1021/jp312774e

    • Related Report
      2013 Annual Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Emission and Transient Absorption Measurements of Substitution Effects of C-C Triple Bonds on Relaxation Processes of the Fluorescent State of Naphthalenes2013

    • Author(s)
      M. Yamaji, H. Maeda, K. Minamida, T. Maeda, K. Asai, G. Konishi and K. Mizuno
    • Journal Title

      Res. Chem. Intermed.

      Volume: 39 Issue: 1 Pages: 321-345

    • DOI

      10.1007/s11164-012-0652-4

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photochemical Synthesis and Electronic Spectra of Fulminene ([6]Phenacene)2013

    • Author(s)
      H. Okamoto, M. Yamaji, S, Goda, K. Sato, H. Sugino and K. Satake
    • Journal Title

      Res. Chem. Intermed.

      Volume: 39 Issue: 1 Pages: 147-159

    • DOI

      10.1007/s11164-012-0639-1

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 5-[4-(Dimethylamino)phenyl]-2-benzamido pyrazines: Fluorescent dyes based on Cypridina oxyluciferin2013

    • Author(s)
      Takashi Hirano, Tatsuki Nakagawa, Ai Kodaka, Shojiro Maki, Haruki Niwa, and Minoru Yamaji, (Takashi Hirano)
    • Journal Title

      Research on Chemical Intermediates

      Volume: Vol.39 Issue: 1 Pages: 233-245

    • DOI

      10.1007/s11164-012-0645-3

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Substitution effects of C≡C triple bonds on the fluorescent properties of perylenes studied by emission and transient absorption measurements2013

    • Author(s)
      M. Yamaji, H. Maeda, Y. Nanai and K. Mizuno
    • Journal Title

      Chem. Phys. Lett.

      Volume: 536 Pages: 72-76

    • DOI

      10.1016/j.cplett.2012.03.108

    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Substitution Effects of C-C Triple Bonds on Deactivation Processes from the Fluorescent State of Pyrene Studied by Emission and Transient Absorption Measurements2013

    • Author(s)
      M. Yamaji, H. Maeda, Y. Nanai and K. Mizuno
    • Journal Title

      ISRN Physical Chemistry

      Volume: - Pages: 1-7

    • DOI

      10.5402/2012/103817

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Substitution Effects of C-C Triple Bonds on Deactivation Processes from the Fluorescent State of Pyrene Studied by Emission and Transient Absorption Measurements2012

    • Author(s)
      M. Yamaji, H. Maeda, Y. Nanai and K. Mizuno
    • Journal Title

      ISRN Physical Chemistry

      Volume: 2012 Pages: 7-7

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Substitution effects of C ≡C triple bonds on the fluorescent properties of perylenes studied by emission and transient absorption measurements2012

    • Author(s)
      M. Yamaji, H. Maeda, Y. Nanai and K. Mizuno
    • Journal Title

      Chem. Phys. Lett.

      Volume: 536 Pages: 72-76

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Characteristics of [6]phenacene thin film field-effect transistor2012

    • Author(s)
      N. Komura, H. Goto, X. He, H. Mitamura, R. Eguchi, Y. Kaji, H. Okamoto, Y. Sugawara, S. Gohda, K. Sato and Y. Kubozono
    • Journal Title

      Appl. Phys. Lett

      Volume: 101

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis of Picene from 1,2-Di(1 -naphthyl)ethane by 9-Fluorenone-Sensitized Photolysis2011

    • Author(s)
      H. Okamoto, M. Yamaji, S. Gohda, Y. Kubozono, N. Komura, K. Sato, H. Sugino and K. Satake
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 2758-2761

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Photochemical and photophysical properties of dibenzoylmethane derivatives within protein2011

    • Author(s)
      M. Marin, V. Lhiaubet-Vallet, C. Paris, M. Yamaji and M. A. Miranda
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 10 Pages: 1474-1479

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis of Picene from 1,2-Di(1 -naphthyl)ethane by 9-Fluorenone-Sensitized Photolysis2011

    • Author(s)
      H. Okamoto, M. Yamaji, S. Gohda, Y. Kubozono, N. Komura, K. Sato, H. Sugino and K. Satake
    • Journal Title

      Org. Lett.

      Volume: 13 Pages: 2758-2761

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Metal-intercalated aromatic hydrocarbons : a new class of carbon-based superconductors2011

    • Author(s)
      Y. Kubozono, H. Mitamura, X.-S. Lee, X.-X. He, Y. Yamanari, Y. Takahashi, Y. Suzuki, Y. Kaji, R. Eguchi, K. Akaike, T. Kambe, H. Okamoto, A. Fujiwara, T. Kato, T.-I. Kosugi and H. Aoki
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 13 Pages: 16476-16493

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Development of new aromatic molecule superconductors2011

    • Author(s)
      Y. Kubozono, T. Kambe, H. Okamoto and A. Fujiwara
    • Journal Title

      Fain Kemikaru

      Volume: 40 Pages: 5-13

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis of Picene from 1,2-Di(1-naphthyl)e thane by 9-Fluorenone-Sensitized Photolysis2011

    • Author(s)
      H.Okamoto, et al.
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 2758-2761

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Synthetic Photocyclization for Phenacenes Using a Continuous Flow Reactor

    • Author(s)
      H. Okamoto, T. Takane, S. Gohda, Y. Kubozono, K. Sato, M. Yamaji, and K. Satake
    • Journal Title

      Chem. Lett.

      Volume: (in press)

    • NAID

      130004868234

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Photochemical Synthesis and Electronic Spectra of Fulminene ([6]Phenacene)

    • Author(s)
      H.Okamoto, et al.
    • Journal Title

      Res.Chem.Intermed.

      Volume: (印刷中)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Emission and Transient Absorption Measurements of Substitution Effects of C-C Triple Bonds on Relaxation Processes of the Fluorescent State of Naphthalenes

    • Author(s)
      M.Yamaji, et al.
    • Journal Title

      Res.Chem.Intermed.

      Volume: (印刷中)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] Photochemical Synthesis of [n]Phenacenes : 9-Fluorenone Sensitized Photocyclization of 1, 2-Diarylethane2013

    • Author(s)
      H. Okamoto, M. Yamaji, S. Gohda, Y. Kubozono and K. Satake
    • Organizer
      2013 Korea-Japan Frontier Photoscience
    • Place of Presentation
      Seoul (Korea)
    • Year and Date
      2013-11-25
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] 過渡吸収と時間分解EPR測定による1, 3-ジケントン化合物の分子構造と光化学的性質の研究2013

    • Author(s)
      山路稔・ 中島悟・ 秋山公男・ 手老省三・ 加藤真一郎・ 中村洋介
    • Organizer
      2013光化学討論会
    • Year and Date
      2013-09-12
    • Related Report
      2013 Final Research Report
  • [Presentation] Mallory環化によるフェナセンの合成 : 光ファイバーマイクロリアクターを用いる合成の効率化2013

    • Author(s)
      岡本秀毅・ 郷田慎・ 柴田明菜・ 佐藤かおり・ 山路稔・ 佐竹恭介
    • Organizer
      2013光化学討論会
    • Place of Presentation
      松山
    • Year and Date
      2013-09-12
    • Related Report
      2013 Final Research Report
  • [Presentation] Photochemical Synthesis of [n]Phenacenes: 9-Fluorenone Sensitized Photocyclization of 1,2-Diarylethane2013

    • Author(s)
      H. Okamoto, M. Yamaji,S. Gohda,Y. Kubozono and K. Satake
    • Organizer
      2013 Korea-Japan Frontier Photoscience
    • Place of Presentation
      Seoul, Korea
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 過渡吸収と時間分解EPR測定による1,3-ジケントン化合物の分子構造と光化学的性質の研究2013

    • Author(s)
      小林 敦・山路 稔・中島 悟・秋山公男・手老省三・加藤真一郎・中村洋介
    • Organizer
      2013光化学討論会
    • Place of Presentation
      松山,愛媛
    • Related Report
      2013 Annual Research Report
  • [Presentation] Mallory環化によるフェナセンの合成:光フローリアクタを用いる合成の効率化2013

    • Author(s)
      岡本秀毅・郷田 慎・柴田明菜・佐藤かおり・山路 稔・佐竹恭介
    • Organizer
      2013光化学討論会
    • Place of Presentation
      松山,愛媛
    • Related Report
      2013 Annual Research Report
  • [Presentation] 光誘起 ω 解離機構を用いた広帯域光重合開始剤の開発2013

    • Author(s)
      金田寛之・大島 寿朗・澤田和宏・日高基彦・鎌田賢司・山路 稔
    • Organizer
      平成25年日本化学会関東支部群馬地区地域懇談会
    • Place of Presentation
      日本原子力機構 高崎量子応用研究所
    • Related Report
      2013 Annual Research Report
  • [Presentation] Photochemical synthesis and properties of [n]phenacenes2012

    • Author(s)
      M. Yamaji and H. Okamoto
    • Organizer
      7th Asian Photochemistry Conference
    • Place of Presentation
      Osaka (Japan)
    • Year and Date
      2012-11-12
    • Related Report
      2013 Final Research Report
  • [Presentation] Substituent Effects of C-C Triple Bond on Deactivation Processes of Fluorescence States of Naphthalene2012

    • Author(s)
      M. Yamaji, H. Maeda and K. Mizuno
    • Organizer
      Pyrene and Perylene Derivatives, 2nd International Conference on Element Innovation
    • Place of Presentation
      Kiryu (Japan)
    • Year and Date
      2012-10-19
    • Related Report
      2013 Final Research Report
  • [Presentation] 光化学反応によるフルミネン([6]フェナセン)の合成および電子スペクトル2012

    • Author(s)
      岡本秀毅・ 山路稔・ 郷田慎・ 佐藤かおり・ 杉野久子・ 佐竹恭介
    • Organizer
      2012基礎有機討論会
    • Place of Presentation
      京都
    • Year and Date
      2012-09-20
    • Related Report
      2013 Final Research Report
  • [Presentation] UVサンスクリーンの光熱異性化過程の㏿度論的研究2012

    • Author(s)
      木田真由美・ 山路稔
    • Organizer
      光化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2012-09-13
    • Related Report
      2013 Final Research Report
  • [Presentation] 高励起三重項の光化学(その3)二段階二色レーザー光分解法による芳香族カルボニル化合物の高励起三重項状態のα結合解離過程2012

    • Author(s)
      山路稔・ 蔡喜臣・ 坂本雅典・ 藤塚守・ 真嶋哲朗
    • Organizer
      2012光化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2012-09-13
    • Related Report
      2013 Final Research Report
  • [Presentation] 高励起三重項の光化学(その二段階二色レーザー光分解法による芳香族カルボニル化合物の高励起三重項のα結合解離過程2012

    • Author(s)
      山路 稔,蔡 喜臣,坂本 雅典,藤塚 守,真嶋 哲朗
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京
    • Related Report
      2012 Annual Research Report
  • [Presentation] UV サンスクリーンの光熱異性化反応過程の速度論的研究2012

    • Author(s)
      木田真由美,山路 稔
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京
    • Related Report
      2012 Annual Research Report
  • [Presentation] パルスラジオリシス法を用いた芳香族化合物の一電子還元種の炭素-炭素結合解離による分解反応機構の研究2012

    • Author(s)
      山路 稔,木村 巧,藤乗 幸子,藤塚 守,真嶋 哲朗
    • Organizer
      第55回放射線化学討論会
    • Place of Presentation
      宮城・岩沼
    • Related Report
      2012 Annual Research Report
  • [Presentation] Substituent Effects of C-C Triple Bond on Deactivation Processes of Fluorescence States of Naphthalene, Pyrene and Perylene Derivatives2012

    • Author(s)
      M. Yamaji, H. Maeda and K. Mizuno
    • Organizer
      2nd International Conference on Element Innovation
    • Place of Presentation
      群馬・桐生
    • Related Report
      2012 Annual Research Report
  • [Presentation] Photochemical synthesis and properties of [n]phenacenes2012

    • Author(s)
      M. Yamaji and H. Okamoto
    • Organizer
      7th Asian Photochemistry Conference
    • Place of Presentation
      大阪
    • Related Report
      2012 Annual Research Report
  • [Presentation] Photochemical Synthesis for Organic Semi- and Superconductors : Synthesis and Electronic Spectra of Fulminene ([6]Phenacene)2011

    • Author(s)
      M. Yamaji
    • Organizer
      1st International Conference on Element Innovation
    • Place of Presentation
      Kiryu (Japan)
    • Year and Date
      2011-12-09
    • Related Report
      2013 Final Research Report
  • [Presentation] 高励起三重項の光化学(その2)二色レーザー光分解法による芳香族カルボニル化合物のβ結合解離過程2011

    • Author(s)
      山路稔
    • Organizer
      光化学討論会
    • Place of Presentation
      宮崎
    • Year and Date
      2011-09-06
    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://photochem.chem-bio.st.gunma-u.ac.jp/~yamaji/

    • Related Report
      2013 Final Research Report
  • [Remarks] 群馬大学 学術研究院 分子科学部門 分子光化学研究室

    • URL

      http://photochem.chem-bio.st.gunma-u.ac.jp/~yamaji

    • Related Report
      2013 Annual Research Report
  • [Remarks]

    • URL

      http://www.chem-bio.gunma-u.ac.jp/~yamaji/

    • Related Report
      2011 Annual Research Report
  • [Patent(Industrial Property Rights)] カルボニルフェナセン化合物, 有機発光材料, 有機半導体材料, 及びカルボニルフェナセン化合物の製造方法2014

    • Inventor(s)
      山路稔
    • Industrial Property Rights Holder
      群馬大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-03-19
    • Related Report
      2013 Final Research Report
  • [Patent(Industrial Property Rights)] カルボニルフェナセン化合物、有機発光材料、有機半導体材料、及びカルボニルフェナセン化合物の製造方法2014

    • Inventor(s)
      山路 稔
    • Industrial Property Rights Holder
      群馬大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-03-19
    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] 光重合開始剤2013

    • Inventor(s)
      山路稔
    • Industrial Property Rights Holder
      群馬大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-09-13
    • Related Report
      2013 Final Research Report
  • [Patent(Industrial Property Rights)] 光重合開始剤2013

    • Inventor(s)
      山路 稔
    • Industrial Property Rights Holder
      群馬大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-09-14
    • Related Report
      2013 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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