Development of pH sensitive liposome for organic photovoltaics with fullerene

2013 Fiscal Year Final Research Report

• Project/Area Number: 23560938
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Catalyst/Resource chemical process
• Research Institution: Kumamoto Industrial Research Institute
• Principal Investigator: SHIROSAKI Tomohiro 熊本県産業技術センター(ものづくり室、材料・地域資源室、食品加工室), その他部局等, 研究主任 (70554054)
• Co-Investigator(Kenkyū-buntansha): NAGAOKA Shoji 熊本県産業技術センター, 材料・地域資源室, 研究主幹 (10227994) ; TAKAFUJI Makoto 熊本大学, 大学院自然科学研究科, 准教授 (50332086)
• Co-Investigator(Renkei-kenkyūsha): IHARA Hirotaka 熊本大学, 大学院自然科学研究科, 教授 (10151648) ; SAGAWA Takashi 京都大学, 大学院エネルギー科学研究科, 教授 (20225832)
• Project Period (FY): 2011 – 2013
• Keywords: 太陽電池 / 太陽光発電 / 超分子化学 / 合成化学 / 再生可能エネルギー

Research Abstract

Although liposome has been studied as a career of drug and gene delivery, there are some problems in the release of inclusions of liposome. In order to release drugs in a cell, liposome should be destabilized in acid enviroments such as inside of endocytic vesicles. In this study, we synthesized the phospholipids with disulfide groups in alkyl chains, and prepared pH-sensitive liposome using disulfide groups containing phospholipids. The phospholipid was synthesized from sn-glycero-3-phosphocholine and disulfide group containing fatty acid in the presence of N,N'-diisopropylcarbodiimide and 4-dimethylaminopyridine. The pH-sensitive liposome was prepared at pH7.4, and pH dependent destabilization of the liposome was investigated. pH-sensitive liposome was casted on ITO electrode which was used for organic photovoltaic, and terated with acid. The morphology of the liposome was changed by the treatment of acid.

Research Products

• [Journal Article] Synthesis of a Series of Malonic diester Introduced Fullerene Derivatives (2014)
  • Author(s): T. Shirosaki, R. Harisaki, M. Horikawa, H. Sakurai, S. Nagaoka, H. Ihara
  • Journal Title: Synthetic Communications Volume: Vol. 44 Pages: 275-279
  • Peer Reviewed
• [Journal Article] Preparation and Characterization of dispersible chitosan particles with borate crosslinking and their antimicrobial and antifungal activity (2012)
  • Author(s): K. Saita, S. Nagaoka, T. Shirosaki, M. Horikawa, S. Matsuda, H. Ihara
  • Journal Title: Carbohydrate Research Volume: Vol. 349 Pages: 52-58
  • Peer Reviewed
• [Journal Article] Facil and versatile method for preparing core-shell microsphere with controlled surface structures based on silica particles-monolayer (2011)
  • Author(s): A. Uchimura, S. Kubota, S. Yamada, T. Wakiya, M. Takafuji, T. Shirosaki, S. Nagaoka, H. Ihara
  • Journal Title: Materials Chemistry and Physics Volume: Vol. 129 Pages: 871-880
  • Peer Reviewed
• [Journal Article] Chitosan sub-micron particles prepared using sulfate ion salt as bacteriostatic materials in neutral pH condition (2011)
  • Author(s): K. Saita, S. Nagaoka, T. Shirosaki, M. Horikawa, S. Matsuda, H. Ihara
  • Journal Title: Journal of Biomaterials and Nanobiotechnology Volume: Vol. 2 Pages: 347-352
  • Peer Reviewed
• [Journal Article] Malonate Methanofullerene Derivatives as Electron Acceptors in Bulk-Hetero junction Solar Cells (2011)
  • Author(s): T. Shiroasaki, R. Harisaki, M. Horikawa, S. Nagaoka, H. Jintoku, M. Takafuji, H. Ihara
  • Journal Title: Proceedings of Pusan-Gyeognam/Kyushu-Seibu Joint Symposium On High Polymaers (15th) and Fibers (13th) Volume: Vol.15 Pages: 241-242
  • Peer Reviewed
• [Journal Article] Preparation and Characterization of Maltose-Pendant Polymer/Mica Nanocomposites and Their Application to Oxygen Gas Narrier Films
  • Author(s): Hideo Sakurai, S. Nagaoka, M. Horikawa, T. Shirosaki, S. Kubota, K. Hamada, M. Takafuji, H. Ihara
  • Journal Title: Journal of Biomaterials and Nanobiotechnology Volume: (印刷中)
  • Peer Reviewed
• [Presentation] Synthesis of a Series of Malonic Diester Introduced Fullerene Derivatives (2013)
  • Author(s): T. Shirosaki, S. Nagaoka, R. Harisaki, M. Horikawa, M. Takafuji, H. Ihara
  • Organizer: as International Conference on Diamond and Carbon Materials 2013
  • Place of Presentation: Riva del Garda(Italy)
  • Year and Date: 20130902-05
• [Presentation] ジスルフィド結合含有リン脂質による放出制御リポソームの開発 (2013)
  • Author(s): 城崎智洋, 高藤誠, 堀川真希, 永岡昭二
  • Organizer: 第62回高分子年次大会
  • Place of Presentation: 国立京都国際会館(京都市)
  • Year and Date: 20130529-31
• [Presentation] Synthesis and Characterization of Novel Phospholipids Containing Disulfide Groups in Alkyl Chains for pH Sensitive Liposome (2013)
  • Author(s): T. Shirosaki, M. Takafuji, M. Horikawa, S. Nagaoka
  • Organizer: 第23回日本MRS年次大会
  • Place of Presentation: 横浜情報文化センター(横浜市)
  • Year and Date: 2013-12-09
• [Presentation] Flexible Dye-Sensitized Solar Cells Fabricated with ZnO Nanoparticles using Silsesquioxane Film (2013)
  • Author(s): M. Karaoke, H. Sakurai, T. Shirosaki, M. Horikawa, T. Ooba, S. Nagaoka, M. Takafuji, H. Ihara
  • Organizer: 2013 Pusan-Gyeongnam/Kyushu-Seibu Joint Symposium On High Polymers (16th) and Fibers (14th)
  • Place of Presentation: Saga University(佐賀市)
  • Year and Date: 2013-11-09
• [Presentation] Synthesis and Characterization of Malonate Methanofullerene Derivatives for Bulk-Heterojunction Solar Cells (2012)
  • Author(s): T. Shirosaki, R. Harisaki, M. Horikawa, S. Nagaoka, H. Jintoku, M. Takafuji, H. Ihara
  • Organizer: The 9th SPSJ International Polymer Conference
  • Place of Presentation: 神戸国際会議場(神戸市)
  • Year and Date: 2012-12-12
• [Presentation] Synthesis and Characterization of PEDOT Thin Films based on Sulfated Polysaccharides (2012)
  • Author(s): M. Horikawa, T. Fujiki, T. Shirosaki, S. Nagaoka, R. Harisaki, H. Sakurai, M. Takafuji, H. Ihara
  • Organizer: The 9th SPSJ International Polymer Conference
  • Place of Presentation: 神戸国際会議場(神戸市)
  • Year and Date: 2012-12-12
• [Presentation] Preparation of Oligosaccharide Pendant Polymer-Clay Nanocomposite as Gas Barrier Material and their Characterization (2012)
  • Author(s): H. Sakurai, S. Nagaoka, M. Horikawa, T. Shirosaki, S. Kubota, K. Hamada, M. Takafuji, H. Ihara
  • Organizer: 2012 MRS Fall Meeting&Exhibit
  • Place of Presentation: Hynes Convention Center(Boston, USA)
  • Year and Date: 2012-11-29
• [Presentation] PV用有機n型半導体としてのマロン酸誘導体付加型フラーレンの開発 (2012)
  • Author(s): 針崎良太, 城崎智洋, 堀川真希, 永岡昭二, 佐川尚, 高藤誠, 伊原博隆
  • Organizer: 2012年日本化学会西日本大会
  • Place of Presentation: 佐賀大学(佐賀県)
  • Year and Date: 2012-11-10
• [Presentation] 多糖類を骨格としたPEDOT薄膜の合成とそのキャラクタリゼーション (2012)
  • Author(s): 藤木孝憲, 堀川真希, 城崎智洋, 永岡昭二, 針崎良太, 明見秀彦, 山本勝政, 櫻井英夫, 高藤誠, 伊原博隆
  • Organizer: 2012年日本化学会西日本大会
  • Place of Presentation: 佐賀大学(佐賀県)
  • Year and Date: 2012-11-10
• [Presentation] ビスコース相分離法によるコア-シェル型セルロース/硬質無機材料複合粒子の開発 (2012)
  • Author(s): 永岡昭二, 城崎智洋, 堀川真希, 高藤誠, 伊原博隆
  • Organizer: 第17回高分子ミクロスフェア討論会
  • Place of Presentation: 東北大学(宮城県)
  • Year and Date: 2012-11-08
• [Presentation] 高分散性フラーレン誘導体の合成と有機薄膜太陽電池への展開 (2012)
  • Author(s): 針崎良太, 城崎智洋, 堀川真希, 永岡昭二, 高藤誠, 伊原博隆
  • Organizer: 第57回高分子夏季大学
  • Place of Presentation: 琵琶湖ホテル(滋賀県)
  • Year and Date: 2012-07-18
• [Presentation] 有機/無機ハイブリッド微粒子を用いた色素増感太陽電池の高効率化に関する研究 (2012)
  • Author(s): 山下太輔, 堀川真希, 城崎智洋, 永岡昭二, 高藤誠, 伊原博隆
  • Organizer: 第57回高分子夏季大学
  • Place of Presentation: 琵琶湖ホテル(滋賀県)
  • Year and Date: 2012-07-18
• [Presentation] 硫酸セルロースを骨格としたPEDOT薄膜の合成とそのキャラクタリゼーション (2012)
  • Author(s): 藤木孝憲, 堀川真希, 城崎智洋, 永岡昭二, 櫻井英夫, 高藤誠, 伊原博隆
  • Organizer: 第49回化学関連支部合同九州大会
  • Place of Presentation: 北九州国際会議場(福岡県)
  • Year and Date: 2012-06-30
• [Presentation] Annealing Temperature Dependence of the Photoelectrochemical Properties of Dye-Sensitized Solar Cells Fabricated with ZnO Nanoparticles (2011)
  • Author(s): H. Yonekawa, T. Shirosaki, M. Horikawa, S. Nagaoka, M. Nagata, H. Jintoku, M. Takafuji , H. Ihara
  • Organizer: 第21回日本MRS学術シンポジウム
  • Place of Presentation: 横浜情報文化文化センター(神奈川県)
  • Year and Date: 2011-12-19
• [Presentation] Malonate Methano fullerene Derivatives as Electron Acceptors in Bulk-Heterojunction Solar Cells (2011)
  • Author(s): T. Shiroasaki, R. Harisaki, M. Horikawa, S. Nagaoka, H. Jintoku, M. Takafuji, H. Ihara
  • Organizer: Pusan-Gyeognam/Kyushu - Seibu Joint Symposium On High Polymaers (15th) and Fibers (13th)
  • Place of Presentation: 釜山大学(韓国)
  • Year and Date: 2011-10-27
• [Presentation] Dye-Sensitized Solar Cells Fabricated with ZnO Nanoparticles for High Conversion Efficiency (2011)
  • Author(s): H. Yonekawa, T. Shirosaki, M. Horikawa, S. Nagaoka, M. Takafuji, H. Ihara
  • Organizer: 3rd Asian Symposium on Advanced Materials
  • Place of Presentation: 九州大学(福岡県)
  • Year and Date: 2011-09-21
• [Presentation] 光電変換アクセプターユニットとしての高分散性フラーレン誘導体の開発 (2011)
  • Author(s): 針崎良太, 城崎智洋, 堀川真希, 永岡昭二, 佐川尚, 高藤誠, 伊原博隆
  • Organizer: 第48回化学関連支部合同大会
  • Place of Presentation: 北九州国際会議場(福岡県)
  • Year and Date: 2011-07-09
• [Book] ゲルの安定化と機能性付与・次世代への応用展開 (2013)
  • Author(s): 城崎智洋, 他
  • Total Pages: 4
  • Publisher: 技術情報協会
• [Patent(Industrial Property Rights)] 太陽電池 (2013)
  • Inventor(s): 永岡昭二, 城崎智洋, 堀川真希, 伊原博隆, 櫻井英夫, 吉田一浩, 大場智之
  • Industrial Property Rights Holder: 熊本県, 国立大学法人熊本大学, JNC株式会社
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2013-224348
  • Filing Date: 2013-10-29
  • Overseas
• [Patent(Industrial Property Rights)] ガスバリア性コート剤 (2012)
  • Inventor(s): 高藤誠, 櫻井英夫, 伊原博隆, 永岡昭二, 堀川真希, 城崎智洋, 浜田和宏, 久保田修壮
  • Industrial Property Rights Holder: 国立大学法人熊本大学, 熊本県, 興人フィルム&ケミカルズ株式会社
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2012-232845
  • Filing Date: 2012-10-22
  • Overseas
• [Patent(Industrial Property Rights)] 導電性ポリマー組成物 (2012)
  • Inventor(s): 堀川真希, 永岡昭二, 城崎智洋, 伊原博隆, 櫻井英夫, 高藤誠, 山本勝政, 明見秀彦
  • Industrial Property Rights Holder: 熊本県, 国立大学法人熊本大学, 住友精化株式会社
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2012-247188
  • Filing Date: 2012-10-09
  • Overseas
• [Patent(Industrial Property Rights)] 色素増感太陽電池 (2011)
  • Inventor(s): 城崎智洋, 永岡昭二, 堀川真希, 伊原博隆, 高藤誠, 神徳啓邦, 田中巧, 後藤武弘
  • Industrial Property Rights Holder: 熊本県, 国立大学法人熊本大学, 大東化成工業株式会社
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 特願2011-235486
  • Filing Date: 2011-10-26
  • Overseas