Development of fluorescent dyes in the near-infrared region for bio-analysis

• Project/Area Number: 25410152
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Analytical chemistry
• Research Institution: Nagahama Institute of Bio-Science and Technology
• Principal Investigator: SASAKI Shin-ichi 長浜バイオ大学, バイオサイエンス学部, 准教授 (50317294)
• Co-Investigator(Renkei-kenkyūsha): SUZUKI Koji 慶應義塾大学, 理工学部, 教授 (80154540) ; TAMIAKI Hitoshi 立命館大学, 薬学部, 教授 (00192641)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2013: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
• Keywords: 蛍光 / 分子認識 / 超分子 / 光合成 / クロロフィル / センシング / 太陽電池 / アミン / アニオン / ウレア / クルチウス転移

Outline of Final Research Achievements

Aiming at the analytical applications in the field of biochemistry, functional fluorescent dyes were synthesized based on naturally occurring (bacterio)chlorophylls. 1) The synthetic C3-ureidochlorin showed fluorescence emission spectral responses with the addition of anions in dichloromethane, 2) a series of carboxylated chlorins were synthesized and the detection of additional amine in THF was demonstrated by both visible absorption and fluorescence emission spectroscopies, 3) the selective detection of histidine was demonstrated using monomeric/oligomeric zinc chlorins in an aqueous buffer solution, and 4) bacteriochlorophyll-a derivatives possessing different substituents at the C13-position were synthesized, which showed fluorescence emission maxima in the longer wavelength region (>800nm).

Research Products

• [Journal Article] Synthesis of chlorophyll derivatives possessing an S-substituted thiomethyl group at the 3-position and their optical properties (2016)
  • Author(s): K. Kim, M. Yoshizato, S. Sasaki, H. Tamiaki
  • Journal Title: Tetrahedron Volume: 72 Issue: 4 Pages: 504-511
  • DOI: 10.1016/j.tet.2015.11.066
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Synthesis of carboxylated chlorophylls and their application as functional materials (2015)
  • Author(s): S. Sasaki, X.-F. Wang, T. Ikeuchi, H. Tamiaki
  • Journal Title: J. Porphyrins Phthalocyanines, Volume: 19 Issue: 01-03 Pages: 517-526
  • DOI: 10.1142/s1088424615500418
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Natural-Photosynthesis-Inspired Photovoltaic Cells Using Carotenoid Aggregates as Electron Donors and Chlorophyll Derivatives as Electron Acceptors (2015)
  • Author(s): Taojun Zhuang, Shin-ichi Sasaki, Toshitaka Ikeuchi, Junji Kido, and Xiao-Feng Wang
  • Journal Title: RSC Adv. Volume: 5 Issue: 57 Pages: 45755-45759
  • DOI: 10.1039/c5ra07099f
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Zinc Chlorophyll Aggregates as Hole Transporters for Biocompatible, Natural-Photosynthesis-Inspired Solar Cells (2015)
  • Author(s): Yue Li, Shin-ichi Sasaki, Hitoshi Tamiaki, Cheng-Liang Liu, Jiaxing Song, Wenjing Tian, Enqiang Zheng, Yingjin Wei, Gang Chen, Xueqi Fu, and Xiao-Feng Wang
  • Journal Title: J. Power Sources Volume: 297 Pages: 519-524
  • DOI: 10.1016/j.jpowsour.2015.08.045
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] クロロフィルを利用した有機系太陽電池の開発 (2015)
  • Author(s): 佐々木 真一、民秋 均
  • Journal Title: 化学工業 Volume: 66 Pages: 27-33
• [Journal Article] Esterification of Indoline-Based Small Molecule Donors for Efficient Co-Evaporated Organic Photovoltaics (2014)
  • Author(s): Z. Wang, X-F. Wang, D. Yokoyama, H. Sasabe, J. Kido, Z. Liu, W. Tian, O. Kitao, I. Toshitaka, S. Sasaki
  • Journal Title: Journal of Physical Chemistry C Volume: 118 Issue: 27 Pages: 14785-14794
  • DOI: 10.1021/jp5030608
  • Peer Reviewed
• [Journal Article] Synthesis and photophysical properties of phenyl-sulfanylated chlorophyll derivatives (2014)
  • Author(s): N. Takei, M. Morioka, M. Yoshizato, T. Tanaka, S. Sasaki, S. Itoh, H. Tamiaki, T. Oba
  • Journal Title: Tetrahedron Volume: 70 Issue: 34 Pages: 5109-5113
  • DOI: 10.1016/j.tet.2014.05.115
  • Peer Reviewed
• [Journal Article] Chemosensitive chlorophyll derivatives: optical detection of various amines by synthetic 3-trifluoroacetyl-131-deoxo-pyropheophorbides in solution (2013)
  • Author(s): H. Tamiaki
  • Journal Title: Tetrahedron Volume: 69 Issue: 8 Pages: 1987-1993
  • DOI: 10.1016/j.tet.2012.12.072
  • Peer Reviewed
• [Journal Article] Dicyano-functionalized chlorophyll derivatives with ambipolar characteristic for organic photovoltaics (2013)
  • Author(s): Y.-W. Wang, S. Sasaki, H. Tamiaki, J.-P. Zhang, T. Ikeuchi, Z. Hong, J. Kido, X.-F. Wang
  • Journal Title: Organic Electronics Volume: 14 Issue: 8 Pages: 1972-1979
  • DOI: 10.1016/j.orgel.2013.04.034
  • Peer Reviewed
• [Journal Article] Molecular engineering on a chlorophyll derivative, chlorin e6, for significantly improved power conversion efficiency in dye-sensitized solar cells (2013)
  • Author(s): X.-F. Wang, H. Tamiaki, O. Kitao, T. Ikeuchi, S. Sasaki
  • Journal Title: J. Power Sources Volume: 242 Pages: 860-864
  • DOI: 10.1016/j.jpowsour.2013.05.191
  • Peer Reviewed
• [Journal Article] Synthesis of chlorophyll derivatives directly connecting amino-derived functional groups at the C3-position (2013)
  • Author(s): S. Sasaki, K. Mizutani, M. Kunieda, K. Azuma, H. Tamiaki
  • Journal Title: Chem. Lett. Volume: 42 Issue: 10 Pages: 1212-1213
  • DOI: 10.1246/cl.130564
  • NAID: 10031201313
  • Peer Reviewed
• [Journal Article] Cycloaddition of C3-ethynylated chlorophyll derivative and self-aggregation of zinc chlorin-pyrazole/triazole conjugates (2013)
  • Author(s): S. Sasaki, K. Mizutani, M. Kunieda, H. Tamiaki
  • Journal Title: Tetrahedron Volume: 69 Issue: 46 Pages: 9772-9778
  • DOI: 10.1016/j.tet.2013.09.007
  • Peer Reviewed
• [Presentation] Selective Detection of Histidine in Aqueous Solution Based on Disassembly of Chlorophyll Self-Aggregates (2015)
  • Author(s): Kotowa Sakai, Hitoshi Tamiaki, Toshitaka Ikeuchi, and Shin-ichi Sasaki
  • Organizer: 11th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP15)
  • Place of Presentation: Shiga, Japan
  • Year and Date: 2015-05-29
  • Int'l Joint Research
• [Presentation] C13-Substituent Effects on Synthetic Bacteriochlorophyll Derivatives (2015)
  • Author(s): Shin-ichi Sasaki, and Hitoshi Tamiaki
  • Organizer: 11th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP15)
  • Place of Presentation: Shiga, Japan
  • Year and Date: 2015-05-29
  • Int'l Joint Research
• [Presentation] Construction of Organic Photovoltaic Cells Using Carotenoid as Electron Donor and Chlorophyll Derivatives as Electron Acceptors (2014)
  • Author(s): Shin-ichi Sasaki, Taojun Zhuang, Toshitaka Ikeuchi, and Xiao-Feng Wang
  • Organizer: 2014 International Conference on Artificial Photosynthesis (ICARP2014)
  • Place of Presentation: Hyogo, Japan
  • Year and Date: 2014-11-24 – 2014-11-28
• [Presentation] Synthesis of Chlorophyll Dimers Linked with a Disulfide Bond and Their Intramolecular Energy Transfer (2014)
  • Author(s): Kifa Kim, Mari Yoshizato, Shin-ichi Sasaki, and Hitoshi Tamiaki
  • Organizer: 2014 International Conference on Artificial Photosynthesis (ICARP2014)
  • Place of Presentation: Hyogo, Japan
  • Year and Date: 2014-11-24 – 2014-11-28
• [Presentation] Application of Photosynthetic Pigments in Organic Photovoltaic Cells (2014)
  • Author(s): Xiao-Feng Wang, Shin-ichi Sasaki, and Hitoshi Tamiaki
  • Organizer: 10th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP14)
  • Place of Presentation: Shiga, Japan
  • Year and Date: 2014-05-30 – 2014-06-01
• [Presentation] Effects on Esterification of Indoline-Based Carboxylic Dyes for Fabrication of Organic Solar Cells (2014)
  • Author(s): Shin-ichi Sasaki, Toshitaka Ikeuchi, and Xiao-Feng Wang
  • Organizer: 10th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP14)
  • Place of Presentation: Shiga, Japan
  • Year and Date: 2014-05-30 – 2014-06-01
• [Presentation] Synthetic Study of Carboxylated Chlorins for Application to Dye-Sensitized Solar Cells (2013)
  • Author(s): Shin-ichi Sasaki, Xiao-Feng Wang, Toshitaka Ikeuchi, and Hitoshi Tamiaki
  • Organizer: 9th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP13)
  • Place of Presentation: Shiga, Japan
• [Presentation] スルファニルクロリン類の合成と物性 (2013)
  • Author(s): 大庭亨、武居夏生、舘野雄備、伊原未沙希、森岡みさき、福住高則、伊藤智志、吉里麻理、佐々木真一、民秋均
  • Organizer: 第７回バイオ関連化学シンポジウム
  • Place of Presentation: 名古屋大学東山キャンパス