Structural Control and Various Observations for Chiral Organic Crystals with Polymorphism

• Project/Area Number: 23590002
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Chiba University
• Principal Investigator: MASU hyuma 千葉大学, 工学(系)研究科(研究院), 准教授 (80412394)
• Co-Investigator(Renkei-kenkyūsha): AZUMAYA Isao 東邦大学, 薬学部, 教授 (50276755)
• Project Period (FY): 2011 – 2013
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000); Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 有機結晶 / 結晶多形 / キラリティー / X線回折 / Ｘ線回折

Research Abstract

In this study, we aim to control of chirality in crystalline state via polymorphism of organic crystals.
Aromatic sulfonamides derivatives which have hydrogen-bonding sites were synthesized. These compounds gave chiral polymorphs. Cocrystal of an adamantane-based bisphenol with a bispyridine derivative formed a helical 1D chain via intermolecular hydrogen bonds. The thermodynamically metastable crystalline phases of two ionic liquids (1-alkyl-3-methylimidazolium hexafluorophosphate salts) were obtained by crystallization from the melt. The relationships between crystal structures and thermal properties of these ionic liquids are established.

Research Products

• [Journal Article] Determination of Missing Crystal Structures in the 1-Alkyl-3-methylimidazolium Hexafluorophosphate Series: Implications on Structure-Property Relationships (2013)
  • Author(s): Takatsugu Endo, Hyuma Masu, Kozo Fujii, Takeshi Morita, Hiroko Seki, Sabyasachi Sen, Keiko Nishikawa
  • Journal Title: Crystal Growth & Design Volume: 13 Issue: 12 Pages: 5383-5390
  • DOI: 10.1021/cg401293g
  • Peer Reviewed
• [Journal Article] Hydrogen-Bonded 1D Chains Formed from Adamantane-Based Bisphenols and Bispyridines: Influences of Substitution Groups on Phenol Ring (2013)
  • Author(s): Hyuma Masu, Masahide Tominaga, Isao Azumaya
  • Journal Title: Cryst. Growth Des. Volume: 13 Issue: 2 Pages: 752-758
  • DOI: 10.1021/cg301462v
  • Peer Reviewed
• [Presentation] Search and Control of Polymorphism forβ-Carboline Derivatives (2014)
  • Author(s): Hyuma Masu, Masaru Kitazawa, Tatsuro Nakagama
  • Organizer: 日本化学会第94春期年会
  • Place of Presentation: 名古屋大学(愛知県)
• [Presentation] Search and Control of Polymorphism for β-Carboline Derivatives (2014)
  • Author(s): MASU Hyuma, KITAZAWA Masaru, NAKAGAMA Tatsuro
  • Organizer: 日本化学会第94春期年会
  • Place of Presentation: 名古屋大学（愛知県）
• [Presentation] β-カルボリン類における結晶多形の探索と制御 (2013)
  • Author(s): 北澤大、桝飛雄真、中釜達朗
  • Organizer: 第22回有機結晶シンポジウム
  • Place of Presentation: 北海道大学(北海道)
• [Presentation] 水素結合部位を持つ有機低分子における不斉結晶化と結晶多形の観測 (2013)
  • Author(s): 北澤大、桝飛雄真、中釜達朗
  • Organizer: 有機微量分析研究懇談会創立60周年記念大会シンポジウム
  • Place of Presentation: 長良川国際会議場(岐阜県)
• [Presentation] 芳香族スルホンアミドにおける溶融状態からの結晶多形転移と不斉発現 (2013)
  • Author(s): 桝飛雄真、片桐幸輔、石田馨、坂井貴紘、富永昌英、東屋功
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学(滋賀県)
• [Presentation] 水素結合部位を持つ有機低分子における不斉結晶化と結晶多形の観測 (2013)
  • Author(s): 北澤 大、桝 飛雄真、中釜 達朗
  • Organizer: 有機微量分析研究懇談会創立60周年記念大会シンポジウム
  • Place of Presentation: 長良川国際会議場（岐阜県）
• [Presentation] β-カルボリン類における結晶多形の探索と制御 (2013)
  • Author(s): 北澤 大、桝 飛雄真、中釜 達朗
  • Organizer: 第22回有機結晶シンポジウム
  • Place of Presentation: 北海道大学札幌キャンパス（北海道）
• [Presentation] 芳香族スルホンアミドにおける溶融状態 からの結晶多形転移と不斉発現 (2013)
  • Author(s): 桝飛雄真・片桐幸輔・石田馨・坂井貴紘・富永昌英・東屋功
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
• [Presentation] 芳香族スルホンアミドにおける結晶構造と不斉結晶化現象との相関 (2012)
  • Author(s): 東屋功、桝飛雄真(他8名)
  • Organizer: 第21回有機結晶シンポジウム
  • Place of Presentation: 東京工業大学(東京都)
• [Presentation] 芳香族スルホンアミドにおける結晶構造と不斉結晶化現象との相関 (2012)
  • Author(s): 東屋功・桝飛雄真・片桐幸輔・石田馨・坂井貴紘・川幡正俊・小 原一朗・伊藤文博・瀬高渉・山口健太郎
  • Organizer: 第21回有機結晶シンポジウム
  • Place of Presentation: 東京工業大学すずかけ台キャンパス