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研究者紹介

山田 学(研究詳細)

 環状化合物であるカリックスアレーンは溶液や固体状態で多くの有機分子あるいは金属イオンに対する包接現象や金属イオンへの配位能力など興味ある特性を示す超分子化学の中での有能な人工ホスト分子の一つです。この機能性および立体配座特性によって選択的金属配位や触媒活性、化学センサーとして数多くの有用性が見出されています。

 一方、カリックスアレーン類縁体である含硫黄環状化合物のチアカリックスアレーン(Fig. 1)はフェノールとスルフィド基によって構成される大環状包接化合物であり、架橋部位に硫黄原子が存在することから構造的・電子的にカリックスアレーンとは異なり、金属との親和性が高いという特徴があります。これまで、私はチアカリックスアレーン(Fig. 1)とレアメタル金属との錯体の結晶構造の解明や有機化学的手法によりチアカリックスアレーンに金属との親和性のある元素(酸素、窒素、リン、硫黄など)を含む官能基を導入したレアメタル金属抽出剤の開発を行ってきました。

 チアカリックスアレーンとレアメタル金属との錯体の結晶構造解析では、水溶性p-スルホネートチアカリックス[6]アレーンとレアアースのランタニド金属との錯体を合成し、単結晶X線構造解析により構造決定および超分子形成能について明らかにすることができました(Fig. 2)。溶媒抽出法によるレアメタルに対する抽出能力を検討では、チアカリックス[6]アレーンにカルボキシ基を導入したレアメタル抽出剤は、白金属系金属種が存在する自動車用三元触媒を酸侵出させた溶液から、短時間で且つ高選択・高効率でパラジウム(Pd)やジルコニウム(Zr)のレアメタルを抽出することができることを明らかにしています(Fig. 3)。

 これから、金属に対する高親和性、高認識性を示すチアカリックスアレーンやチアカリックスアレーンの骨格に近い非環状化合物を基にしたレアメタル抽出剤の開発およびレアメタル金属との錯体の結晶構造の解明、レアメタル抽出能の評価を行っていきます。また、開発した抽出剤を用いたアーバンマインからの短時間・高選択・高効率でレアメタルの回収できるシステムの構築を目指したいと思っております。

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山田 学(研究業績)

平成29年度後半(2017年10月)以降の研究業績は秋田大学研究者総覧をご覧ください。

総説(査読有)

  1. Rajiv Gandhi M., Vasudevan S., Shibayama A., Yamada M. (2016) "Graphene and Graphene-Based Composites: A Rising Star in Water Purification - A Comprehensive Overview", ChemistrySelect, 1, 4358-4385.
  2. Yamada M., Rajiv Gandhi M., Uma Maheswara Rao K., Hamada F. (2016) "Thiacalixarenes: Emergent supramolecules in crystal engineering and molecular recognition",Journal of Inclusion Phenomena and Macrocyclic Chemistry, 85, 1-18.

原著論文

  1. Rajiv Gandhi, M.; Yamada, M., Haga, K.; Shibayama, A. (2017) "Synthesis of pincer-type extractants for selective extraction of palladium from PGMs: An improved liquid-liquid extraction approach to current refining processes", Scientific Reports, 7, 8709.
  2. 柴山 敦,山田 学「白金族リサイクルのための抽出剤の開発」, 月刊誌「金属」, Vol. 87(8), pp 698−703 (2017). 
  3. Kimuro, T.; Rajiv Gandhi, M.; Uma Maheswara Rao, K.; Hamada, F.; Yamada, M. (2017) "Palladium(II) sorption of a diethylphosphate-modified thiacalix[6]arene immobilized on amberlite resin", Hydrometallurgy, 171, 254−261.
  4. Senthil, K.; Kalainathan, S.; Kondo, Y.; Hamada, F.; Yamada, M. (2017) "Investigation on the growth, molecular structure and nonlinear optical susceptibilities of 2-[2-(4-ethoxy-phenyl)-vinyl]-1-ethyl-stilbazolium iodide (EESI) by Z-scan technique using He-Ne laser for third-order nonlinear optical applications", Optics & Laser Technology, 90, 242−251.
  5. Kunda, U. M. R.; Yamada, M. (2017) "Sorption of palladium(II) using organophosphorus derivatives based on thiacalix[4]arene impregnated resins from hydrochloric media", Separation Science and Technology, 52 (No. 7), 1153−1159 .
  6. Nivetha, K.; Kalainathan, S.; Yamada, M., Kondo, Y.; Hamada, F. (2017) “Synthesis, growth, and characterization of new stilbazolium derivative single crystal: 2-[2-(2,4-dimethoxy-phenyl)-vinyl]-1-ethyl-pyridinium iodide for third-order NLO applications”, Journal of Materials Science: Materials in Electronics, 28 (No. 7), 5180−5191.
  7. Kunda, U. M. R.; Yamada, M., Hamada, F. (2017) "A 3D supramolecular dimeric assembly based on thiacalix[4]arene by halogen bonding and carbonyl bonding and its dynamic NMR study of conformational preferences", Phosphorus, Sulfur, and Silicon and the Related Elements, 192, 276−282.
  8. Nivetha, K.; Kalainathan, S.; Yamada, M., Kondo, Y.; Hamada, F. (2017) "Synthesis, growth, structure and characterization of 1-Ethyl-2-(2-p-tolyl-vinyl)-pyridinium iodide (TASI) – An efficient material for third-order nonlinear optical applications", Materials Chemistry and Physics, 188, 131−142.
  9. Yamada, M., Rajiv Gandhi, M.; Kaneta, Y.; Hu, Y.; Shibayama, A. (2017) “Calix[4]arene-Based n-Dialkylamino Extractants for Selective Platinum Group Metal Separation from Automotive Catalysts”, ChemistrySelect, 2, 1052−1057.
  10. Yamada, M., Rajiv Gandhi, M.; Sato, D.; Kaneta, Y.; Kimura, N. (2016) "Comparative Study on Palladium(II) Extraction Using Thioamide-Modified Acyclic and Cyclic Extractants", Industrial & Engineering Chemistry Research, 88, 8914−8921.
  11. Nivetha, K.; Kalainathan, S.; Yamada, M., Kondo, Y.; Hamada, F. (2016) "Investigation on the growth, structural, HOMO-LUMO and optical studies of 1-ethyl 2-[2-(4-hydroxy-phenyl)-vinyl]-pyridinium iodide (HSPI) - A new stilbazolium derivative for third-order NLO applications", RSC Advances, 6, 35977−35990.
  12. Karthigha, S.; Kalainathan, S.; Hamada, F.; Yamada, M., Kondo, Y. (2016) "Synthesis, growth and third-order nonlinear optical properties of quinolinium single crystal-PCLQI", RSC Advances, 6, 33159−33169 .
  13. Karthigha, S.; Kalainathan, S.; Kunda, U. M. R.; Hamada, F.; Yamada, M., Kondo, Y. (2016) "Synthesis, Growth, Structural, Optical, Luminescence, Surface and HOMO LUMO analysis of 2-[2-(4-cholro-phenyl)-vinyl]-1-methylquinolinium naphthalene-2-sulfonate organic single crystals grown by slow evaporation technique", Journal of Crystal Growth, 436, 113−124.
  14. Kunda, U.M.R.; Yamada, M., Katagiri, H.; Hamada, F. (2016) "Self-induced organic guest packed in three dimensional architecture based on hetero-alkali metallic sulfonatothiacalix[4]arene", RSC Advances, 6, 19155−19159.
  15. Rajiv Gandhi, M.; Yamada, M., Kondo, Y.; Shibayama, A.; Hamada, F. (2016)"Rapid and selective extraction of Pd(II) ions using the SCS type pincer ligand 1,3-bis(dimethylthiocarbamoyloxy)benzene, and its Pd(II) extraction mechanism, RSC Advances, 6, 1243−1252.
  16. Kunda, U.M.R.; Kimuro, T.; Yamada, M., Kondo, Y.; Hamada, F. (2016) "Solvent Extraction Ability of New Diethyl Phosphate-Modified Thiacalix[6]arene Towards PGM Solution", Heterocycles, 92, 55−63.
  17. Rajiv Gandhi, M.; Yamada, M., Kondo, Y.; Shibayama, A.; Hamada, F. (2015) "p-Sulfonatothiacalix[6]arene-impregnated resins for the sorption of platinum group metals and effective separation of palladium from automotive catalyst residue", Journal of Industrial and Engineering Chemistry, 30, 20−28.
  18. Yamada, M., Rajiv Gandhi, M.; Kondo, Y.; Haga, K.; Shibayama, A.; Hamada, F. (2015) "Selective sorption of palladium by thiocarbamoyl–substituted thiacalix[n]arene derivatives immobilized in amberlite resin: Application to leach liquors of automotive catalysts", RSC Advances, 5, 60506−60517.
  19. Senthil, K.; Kalainathan, S.; Hamada, F.; Yamada, M., Aravindan, P. G. (2015) "Synthesis, growth, structural and HOMO and LUMO, MEP analysis of a new stilbazolium derivative crystal: A enhanced third-order NLO properties with a high laser-induced damage threshold for NLO applications", Optical Materials, 46, 565−577.
  20. Zhou, X.; Koizumi, Y.; Zhang, M.; Natsui, M.; Koyota, S.; Yamada, M., Kondo, Y.; Hamada, F.; Sugiyama, T. (2015) "Cadmium-coordinated supramolecule suppresses tumor growth of T-cell leukemia in mice", Cancer Science, 106, 635−641.
  21. Kimuro, T.; Yamada, M., Hamada, F. (2015) "One-pot synthesis of p-tert-butylthiacalix[6/8]arenes", Journal of Inclusion Phenomena and Macrocyclic Chemistry, 81, 245−249.
  22. Kunda, U. M. R. ; Kimuro, T.; Yamada, M., Kondo, Y.; Hamada, F. (2015) "Synthesis, X-ray Structure and Metal Extraction Abilities of New Diethylphosphate Modified Thiacalix[4]arene", Heterocycles, 91, 989−1000.
  23. Yamada, M., Hamada, F. (2015). "Halogen Interactions in Macrocyclic Thiacalix[4]arene Systems", Crystal Growth & Design, 15, 1889−1897
  24. Kunda, U. M. R.; Yamada, M., Kimuro, T.; Katagiri, H.; Kondo, Y.; Hamada, F. (2015) "A hetero-alkalimetallic (Na, K) three-dimensional supramolecular assembly based on p-sulfonatothiacalix[4]arene", RSC Advances, 5, 30140−30144.
  25. Yamada, M., Rajiv Gandhi, M.; Kondo, Y.; Shibayama, A.; Hamada, F. (2015) "Feasibility studies on palladium extraction from leach liquors of automotive catalysts using p-diethylphosphonomethylthiacalix[6]arene", Separation Science and Technology, 50, 1964−1973.
  26. Rajiv Gandhi, M.; Yamada, M., Kondo, Y.; Shibayama, A.; Hamada, F. (2015) "Selective extraction of Pd(II) ions from automotive catalyst residue in Cl− media by O-thiocarbamoyl-functionalized thiacalix[n]arenes", Hydrometallurgy, 151, 133−140.
  27. Ulzii, M.; Kunda, U. M. R.; Yamada, M., Hamada, F. (2014) "Phosphorylated Thiacalix[6]arene: Synthesis and Characterization of Host-Guest Complex of Selective Pd2+ Ion Extraction", Heterocycles, 89, 2554−2561.
  28. Yamada, M., Hamada, F. (2014) "Supramolecular assembly of p-sulfonatothiacalix[6]arene yttrium complex supported by hydrogen bonding, π-π stacking, and S-π interactions", International Journal of the Society of Materials Engineering for Resources, 20, 230−236.
  29. Yamada, M., Rajiv Gandhi, M.; Kondo, Y.; Hamada, F. (2014) "Synthesis and characterisation
    of p-diethylaminomethylthiacalix[4]arene for selective recovery of platinum from automotive catalyst residue", Supramolecular Chemistry, 26, 620−630.
  30. Yamada, M., Kanazawa, R.; Hamada, F. (2014) "Halogen–halogen interaction and halogen bonding in thiacalixarene systems", CrystEngComm, 16, 2605−2614.
  31. Kondo, Y.; Ulzii, M.; Itoh, S.; Yamada, M.; Hamada, F. (2014) "High selective extraction ability for platinum-group metals based on thiacalix[6]arene derivatives", International Journal of the Society of Materials Engineering for Resources, 20, 103−108.
  32. Rajiv Gandhi, M.; Meenakshi, S.; Yamada, M., Shibayama, A.; Hamada, F. (2014) "Preparation of amino functionalized polymeric resins for selective removal of copper ions" International Journal of the Society of Materials Engineering for Resource, 20, 71−76.
  33. Rajiv Gandhi, M.; Yamada, M., Kondo, Y.; Sato, R.; Hamada, F. (2014) "Synthesis and Characterization of Dimethylthiocarbamoyl-Modified Thiacalix[n]arenes for Selective Pd(II)-Ion Extraction", Industrial & Engineering Chemistry Research, 53, 2559−2565.
  34. Yamada, M.; Hamada, F. (2013) “Supramolecular assemblies with water-soluble p-sulfonatothiacalix[6]arene lanthanide complexes: one-dimensional ‘ladder-type’ coordination polymers and one-dimensional hydrogen-bonded polymers”, CrystEngComm, 15, 5703−5712.
  35. Yamada, M., Ootashiro, Y.; Kondo, Y.; Hamada, F. (2013) "A 3D supramolecular network assembly based on thiacalix[4]arene by halogen-halogen, CH-Br, CH-π, and S-π interactions", Tetrahedron Letters, 54, 1510−1514.
  36. Ulzii, M.; Kondo, Y.; Yamada, M., Hamada, F. (2013) "Metal Extraction Capability for Hybrid Polymers consisted of β-Cyclodextrin and Diatomite", International Journal of the Society of Materials Engineering for Resources, 19, 32−36.
  37. Hamada, F.; Yamada, M., Kondo, Y.; Ito, S.; Akiba, U. (2011) "Channel structure for guest inclusion based on hexameric assembly of thiacalix[4]arene analogue", CrystEngComm, 13, 6920−6922.
  38. Yamada, M., Shimakawa, Y.; Hamada, F. (2011) "Thiacalix[4]arene-alkali metal assemblies: crystal structures and guest-binding capabilities of supramolecular architectures supported by metal coordination and cation-π interactions", Tetrahedron, 67, 7392−7399.
  39. Yamada, M., Hamada, F. (2011) "Thiacalix[4]arene-potassium assemblies: a supramolecular architecture based on coordination polymers and a dimeric structure based on triangular pyramidal arrangements", CrystEngComm, 13, 2494−2499.
  40. Itoh, S.; Li, C.; Yamada, M., Akama, M.; Shimakawa, Y.; Kondo, Y.; Hamada, F. (2010) "Selective Extraction Ability of Thiacalix[6]arene Derivatives from Rare Metal Mixed Solution", International Journal of the Society of Materials Engineering for Resources, 17, 211−215.
  41. Yamada, M.; Shimakawa, Y.; Kondo, Y.; Hamada, F. (2010) "Thiacalix[4]arene-rubidium assembly: supramolecular architecture based on alkali metal coordination and cation-π interactions", CrystEngComm, 12, 1311−1315.
  42. 赤間 三浩,山田 学,島川 良文,伊藤 慎一,李 春斌,柴山 敦,近藤 良彦,濱田 文男 「カルボン酸修飾チアカリックス[6]アレーン誘導体を用いた希少金属溶媒抽出におけるpH及び対イオンの影響」,素材物性学雑誌,第22巻,13−17項 (2009).
  43. Akimoto, K.; Kondo, Y.; Endo, K.; Yamada, M., Aoyama, Y.; Hamada, F. (2008) "A porous coordination architecture assembled by silver triflate and 9,10-bis(3,5-dicyano-1-phenyl)anthracene and its gas adsorption profile", Tetrahedron Letters, 49, 7361−7363.
  44. Yamada, M., Kondo, Y.; Iki, N.; Kabuto, C.; Hamada, F. (2008) "Hydrophobic and metal coordination interacted architecture based on p-tert-butylthiacalix[4]arene-potassium complex and its vapor absorption capability", Tetrahedron Letters, 49, 3906−3911.
  45. Yamada, M., Kondo, Y.; Hamada, F. (2008) "The X-Ray Crystal Structures of p-Sulfonatothiacalix[6]arene Inclusion Complexes with Lanthanide Metal Ions (M = Gd, Ho and Er) and Water Molecules", International Journal of the Society of Materials Engineering for Resources, 15, 50−56.
  46. Yamada, M.; Kondo, Y.; Hamada, F. (2008) "Hydrogen-bonded architecture based on p-sulfonatothiacalix[6]arene complex with dysprosium(III) cations and water molecules", Tetrahedron Letters, 49, 1790−1794.
  47. Yamada, M., Kondo, Y.; Akimoto, K.; Kabuto, C.; Hamada, F. (2007) "Supramolecular assembly based on
    p-sulfonatothiacalix[6]arene with sodium and water molecules", New Journal of Chemistry, 31, 1874−1877.
  48. Yamada, M., Shibayama, A.; Kondo, Y.; Hamada, F. (2007) "Selective Extraction of Precious Metal from Automotive Catalyst Residue by Thiacalix[6]arene Derivatives", International Journal of the Society of Materials Engineering for Resources, 15, 13−15.

知的財産権取得状況:特許(申請中含む)

  1. 山田 学,ムニヤパン ラジブ ガンジー,金田 祐,木村 望,「パラジウム・白金抽出剤、パラジウム・白金の分離方法」,特願2017-148632
  2. 山田 学,ムニヤパン ラジブ ガンジー,芳賀一寿,柴山 敦,「パラジウム抽出剤、パラジウム抽出方法、パラジウム回収方法、パラジウム抽出剤の再生方法、および、パラジウムの反復回収方法 」,特願2017-111863
  3. 濱田文男,クンダ ウマ マシュワラオ,山田 学,近藤良彦,「パラジウム抽出剤、及び、パラジウムの抽出分離方法」,特願2015-027639
  4. 近藤 良彦,山田 学,濱田 文男,「新規化合物、金属抽出剤、並びにパラジウム及び白金の少なくともいずれかの抽出方法」,特願2013-045533
  5. 濱田 文男,近藤 良彦,山田 学,「環状フェノール硫化物の製造方法」,特願2013-053442
  6. 山田 学,近藤 良彦,濱田 文男,「白金の抽出分離方法」,特願2013-069744
  7. 濱田 文男,近藤 良彦,山田 学 「シクロデキストリンとシリカ含有物質との複合材料、及びその製造方法、並びにガス吸着剤」,特許第5892847号
  8. 濱田 文男,近藤 良彦,山田 学 「シクロデキストリンと多孔質シリカ粒子との複合材料、及びその製造方法、金属抽出剤、セシウム抽出剤、並びにガス吸着剤」,特許第5892837号
  9. 近藤 良彦,李 春斌,山田 学,濱田 文男 「レアメタル抽出剤」,特許第5472722号,中国特許 ZL 2009 8 0104567.0,米国特許 US 8,500,846 B2
  10. 濱田 文男,山田 学,近藤 良彦 「ガス吸蔵能力を有する環状化合物−金属錯体類縁体」,特開2008-308470
  11. 近藤 良彦,柴山 敦,濱田 文男,山田 学,赤間 三浩,今井 貴紀 「レアメタル,白金族系金属抽出剤及びレアメタル,白金族系金属抽出方法」,特許第5145536号,米国特許 US 8,038,969 B2

受賞等

  • 平成20年度 日本素材物性学会 若手論文賞
  • 平成23年度 日本素材物性学会 優秀論文発表賞
  • 平成25年 素材物性学国際会議 (ICMR2013 AKITA) 優秀論文賞

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Yamada Manabu [ Detail of Research ]

Calixarenes are one of the most studied molecular scaffolds in supramolecular chemistry because of their intriguing properties such as inclusion behaviors of many organic components or metal ions and their metal–coordination capabilities for metal ions in solution and in the solid state. Their functional and conformational characteristics lead to many applications in selective metal coordination, catalytic activity, and chemical sensor. On the other hand, thiacalixarenes composed of benzene rings, linked via sulfur bridges have a high affinity toward a wide range of metal ions in comparison with calixarenes (Fig. 1). So far, we have investigated single-crystal X-ray diffraction studies of rare metal complexes with thiacalixarenes and development of thiacalixarenes introduced functional groups containing elements (oxygen, nitrogen, phosphorus, sulfur, etc) as new extractants for rare metal recovery.

In the crystallographic analysis of rare metal complexes with water-soluble p-sulfonatothiacalix[6]arene, we have elucidated crystal structures and supramolecular assembly formations of the lanthanide complexes with p-sulfonatothiacalix[6]arene (Fig. 2).

The investigation of extractabilities of carboxylic acid modified thiacalix[6]arene derivatives as extractants for rare metals by solvent extraction showed that the compound extracts palladium (Pd) and zirconium (Zr) from waste solution which leached automotive catalyst (including platinum-group metals) by acid (Fig. 3). We will conduct; (1) development of thiacalixarene derivatives and acyclic compounds that are similar to the thiacalixarene backbone as new extractants for rare metal recovery, and (2) elucidation of the crystal structure of the rare metal complexes with thiacalixarenes or acyclic compounds, (3) evaluation of the extractabilities of new extractants for rare metal recovery from urban mine.

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The publications and reviews since October 2017 are on the web of Akita University Academic Research stuff

Yamada Manabu [ Reviews ]

  1. Rajiv Gandhi, M.; Vasudevan, S.; Shibayama, A.; Yamada, M. "Graphene and Graphene-Based Composites: A Rising Star in Water Purification - A Comprehensive Overview", ChemistrySelect, Vol. 1, 4358-4385 (2016).
  2. Yamada, M.; Rajiv Gandhi, M.; Uma Maheswara Rao, K.; Hamada, F. "Thiacalixarenes: Emergent supramolecules in crystal engineering and molecular recognition", Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 85, pp. 1-18(2016).

Yamada Manabu [ Publications ]

  1. Rajiv Gandhi, M.; Yamada, M.; Haga, K.; Shibayama, A. "Synthesis of pincer-type extractants for selective extraction of palladium from PGMs: An improved liquid-liquid extraction approach to current refining processes", Scientific Reports, Vol. 7, pp. 8709 (2017).
  2. Kimuro, T.; Rajiv Gandhi, M.; Uma Maheswara Rao, K.; Hamada, F.; Yamada, M. "Palladium(II) sorption of a diethylphosphate-modified thiacalix[6]arene immobilized on amberlite resin", Hydrometallurgy, Vol. 171, pp. 254−261 (2017).
  3. Senthil, K.; Kalainathan, S.; Kondo, Y.; Hamada, F.; Yamada, M. "Investigation on the growth, molecular structure and nonlinear optical susceptibilities of 2-[2-(4-ethoxy-phenyl)-vinyl]-1-ethyl-stilbazolium iodide (EESI) by Z-scan technique using He-Ne laser for third-order nonlinear optical applications", Optics & Laser Technology, Vol. 90, pp. 242−251 (2017).
  4. Kunda, U. M. R.; Yamada, M. "Sorption of palladium(II) using organophosphorus derivatives based on thiacalix[4]arene impregnated resins from hydrochloric media", Separation Science and Technology, Vol. 52 (No. 7), pp 1153−1159 (2017).
  5. Nivetha, K.; Kalainathan, S.; Yamada, M.; Kondo, Y.; Hamada, F. “Synthesis, growth, and characterization of new stilbazolium derivative single crystal: 2-[2-(2,4-dimethoxy-phenyl)-vinyl]-1-ethyl-pyridinium iodide for third-order NLO applications”, Journal of Materials Science: Materials in Electronics, Vol. 28 (No. 7), pp. 5180−5191 (2017).
  6. Kunda, U. M. R.; Yamada, M.; Hamada, F. "A 3D supramolecular dimeric assembly based on thiacalix[4]arene by halogen bonding and carbonyl bonding and its dynamic NMR study of conformational preferences", Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 192, pp. 276−282 (2017).
  7. Nivetha, K.; Kalainathan, S.; Yamada, M.; Kondo, Y.; Hamada, F. "Synthesis, growth, structure and characterization of 1-Ethyl-2-(2-p-tolyl-vinyl)-pyridinium iodide (TASI) – An efficient material for third-order nonlinear optical applications", Materials Chemistry and Physics, Vol. 188, pp. 131−142 (2017).
  8. Yamada, M.; Rajiv Gandhi, M.; Kaneta, Y.; Hu, Y.; Shibayama, A. “Calix[4]arene-Based n-Dialkylamino Extractants for Selective Platinum Group Metal Separation from Automotive Catalysts”, ChemistrySelect, Vol. 2, pp. 1052−1057 (2017).
  9. Yamada, M.; Rajiv Gandhi, M.; Sato, D.; Kaneta, Y.; Kimura, N. "Comparative Study on Palladium(II) Extraction Using Thioamide-Modified Acyclic and Cyclic Extractants", Industrial & Engineering Chemistry Research, Vol. 88, pp. 8914−8921 (2016).
  10. Nivetha, K.; Kalainathan, S.; Yamada, M.; Kondo, Y.; Hamada, F. "Investigation on the growth, structural, HOMO-LUMO and optical studies of 1-ethyl 2-[2-(4-hydroxy-phenyl)-vinyl]-pyridinium iodide (HSPI) - A new stilbazolium derivative for third-order NLO applications", RSC Advances, Vol. 6, pp. 35977−35990 (2016).
  11. Karthigha, S.; Kalainathan, S.; Hamada, F.; Yamada, M.; Kondo, Y. "Synthesis, growth and third-order nonlinear optical properties of quinolinium single crystal-PCLQI", RSC Advances, Vol. 6, pp. 33159−33169 (2016).
  12. Karthigha, S.; Kalainathan, S.; Kunda, U. M. R.; Hamada, F.; Yamada, M.; Kondo, Y. "Synthesis, Growth, Structural, Optical, Luminescence, Surface and HOMO LUMO analysis of 2-[2-(4-cholro-phenyl)-vinyl]-1-methylquinolinium naphthalene-2-sulfonate organic single crystals grown by slow evaporation technique", Journal of Crystal Growth, Vol. 436, pp. 113−124 (2016).
  13. Kunda, U.M.R.; Yamada, M.; Katagiri, H.; Hamada, F. "Self-induced organic guest packed in three dimensional architecture based on hetero-alkali metallic sulfonatothiacalix[4]arene", RSC Advances, Vol. 6, pp. 19155−19159 (2016).
  14. Rajiv Gandhi, M.; Yamada, M.; Kondo, Y.; Shibayama, A.; Hamada, F. "Rapid and selective extraction of Pd(II) ions using the SCS type pincer ligand 1,3-bis(dimethylthiocarbamoyloxy)benzene, and its Pd(II) extraction mechanism, RSC Advances, Vol. 6, pp. 1243−1252 (2016).
  15. Kunda, U.M.R.; Kimuro, T.; Yamada, M.; Kondo, Y.; Hamada, F. "Solvent Extraction Ability of New Diethyl Phosphate-Modified Thiacalix[6]arene Towards PGM Solution", Heterocycles, Vol. 92, pp. 55−63 (2016).
  16. Rajiv Gandhi, M.; Yamada, M.; Kondo, Y.; Shibayama, A.; Hamada, F. "p-Sulfonatothiacalix[6]arene-impregnated resins for the sorption of platinum group metals and effective separation of palladium from automotive catalyst residue", Journal of Industrial and Engineering Chemistry, Vol. 30, pp. 20−28 (2015).
  17. Yamada, M.; Rajiv Gandhi, M.; Kondo, Y.; Haga, K.; Shibayama, A.; Hamada, F. "Selective sorption of palladium by thiocarbamoyl–substituted thiacalix[n]arene derivatives immobilized in amberlite resin: Application to leach liquors of automotive catalysts", RSC Advances, Vol. 5, pp. 60506−60517 (2015).
  18. Senthil, K.; Kalainathan, S.; Hamada, F.; Yamada, M.; Aravindan, P. G. "Synthesis, growth, structural and HOMO and LUMO, MEP analysis of a new stilbazolium derivative crystal: A enhanced third-order NLO properties with a high laser-induced damage threshold for NLO applications", Optical Materials, Vol. 46, pp. 565−577 (2015).
  19. Zhou, X.; Koizumi, Y.; Zhang, M.; Natsui, M.; Koyota, S.; Yamada, M.; Kondo, Y.; Hamada, F.; Sugiyama, T. "Cadmium-coordinated supramolecule suppresses tumor growth of T-cell leukemia in mice", Cancer Science, Vol. 106, pp. 635−641 (2015).
  20. Kimuro, T.; Yamada, M.; Hamada, F. "One-pot synthesis of p-tert-butylthiacalix[6/8]arenes", Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 81, pp. 245−249 (2015).
  21. Kunda, U. M. R. ; Kimuro, T.; Yamada, M.; Kondo, Y.; Hamada, F. "Synthesis, X-ray Structure and Metal Extraction Abilities of New Diethylphosphate Modified Thiacalix[4]arene", Heterocycles, Vol. 91, pp. 989−1000 (2015).
  22. Yamada, M.; Hamada, F. "Halogen Interactions in Macrocyclic Thiacalix[4]arene Systems", Crystal Growth & Design, Vol. 15, pp. 1889−1897 (2015).
  23. Kunda, U. M. R.; Yamada, M.; Kimuro, T.; Katagiri, H.; Kondo, Y.; Hamada, F. "A hetero-alkalimetallic (Na, K) three-dimensional supramolecular assembly based on p-sulfonatothiacalix[4]arene", RSC Advances, Vol. 5, pp. 30140−30144 (2015).
  24. Yamada, M.; Rajiv Gandhi, M.; Kondo, Y.; Shibayama, A.; Hamada, F. "Feasibility studies on palladium extraction from leach liquors of automotive catalysts using p-diethylphosphonomethylthiacalix[6]arene", Separation Science and Technology, Vol. 50, pp. 1964−1973 (2015).
  25. Rajiv Gandhi, M.; Yamada, M.; Kondo, Y.; Shibayama, A.; Hamada, F. "Selective extraction of Pd(II) ions from automotive catalyst residue in Cl− media by O-thiocarbamoyl-functionalized thiacalix[n]arenes", Hydrometallurgy, Vol. 151, pp. 133−140 (2015).
  26. Ulzii, M.; Kunda, U. M. R.; Yamada, M.; Hamada, F. "Phosphorylated Thiacalix[6]arene: Synthesis and Characterization of Host-Guest Complex of Selective Pd2+ Ion Extraction", Heterocycles, Vol. 89, pp. 2554−2561 (2014).
  27. Yamada, M.; Hamada, F. "Supramolecular assembly of p-sulfonatothiacalix[6]arene yttrium complex supported by hydrogen bonding, π-π stacking, and S-π interactions", International Journal of the Society of Materials Engineering for Resources, Vol. 20, pp. 230−236 (2014).
  28. Yamada, M.; Rajiv Gandhi, M.; Kondo, Y.; Hamada, F. "Synthesis and characterisation of
    p-diethylaminomethylthiacalix[4]arene for selective recovery of platinum from automotive catalyst residue", Supramolecular Chemistry, Vol. 26, pp. 620−630 (2014).
  29. Yamada, M.; Kanazawa, R.; Hamada, F. "Halogen–halogen interaction and halogen bonding in thiacalixarene systems", CrystEngComm, Vol. 16, pp. 2605−2614 (2014).
  30. Kondo, Y.; Ulzii, M.; Itoh, S.; Yamada, M.; Hamada, F. "High selective extraction ability for platinum-group metals based on thiacalix[6]arene derivatives", International Journal of the Society of Materials Engineering for Resources, Vol. 20, pp. 103−108 (2014).
  31. Rajiv Gandhi, M.; Meenakshi, S.; Yamada, M.; Shibayama, A.; Hamada, F., "Preparation of amino functionalized polymeric resins for selective removal of copper ions" International Journal of the Society of Materials Engineering for Resource, Vol. 20, pp. 71−76 (2014).
  32. Rajiv Gandhi, M.; Yamada, M.; Kondo, Y.; Sato, R.; Hamada, F. "Synthesis and Characterization of Dimethylthiocarbamoyl-Modified Thiacalix[n]arenes for Selective Pd(II)-Ion Extraction", Industrial & Engineering Chemistry Research, Vol. 53, pp. 2559−2565 (2014).
  33. Yamada, M.; Hamada, F. “Supramolecular assemblies with water-soluble p-sulfonatothiacalix[6]arene lanthanide complexes: one-dimensional ‘ladder-type’ coordination polymers and one-dimensional hydrogen-bonded polymers”, CrystEngComm, Vol. 15, pp 5703−5712, (2013).
  34. Yamada, M.; Ootashiro, Y.; Kondo, Y.; Hamada, F. "A 3D supramolecular network assembly based on thiacalix[4]arene by halogen-halogen, CH-Br, CH-π, and S-π interactions", Tetrahedron Letters, Vol. 54, pp 1510−1514 (2013).
  35. Ulzii, M.; Kondo, Y.; Yamada, M.; Hamada, F. "Metal Extraction Capability for Hybrid Polymers consisted of β-Cyclodextrin and Diatomite", International Journal of the Society of Materials Engineering for Resources, Vol. 19, pp. 32−36 (2013).
  36. Hamada, F.; Yamada, M.; Kondo, Y.; Ito, S.; Akiba, U. "Channel structure for guest inclusion based on hexameric assembly of thiacalix[4]arene analogue", CrystEngComm, Vol. 13, pp 6920−6922 (2011).
  37. Yamada, M.; Shimakawa, Y.; Hamada, F. "Thiacalix[4]arene-alkali metal assemblies: crystal structures and guest-binding capabilities of supramolecular architectures supported by metal coordination and cation-π interactions", Tetrahedron, Vol. 67, pp. 7392−7399 (2011).
  38. Yamada, M.; Hamada, F. "Thiacalix[4]arene-potassium assemblies: a supramolecular architecture based on coordination polymers and a dimeric structure based on triangular pyramidal arrangements", CrystEngComm, Vol. 13, pp. 2494−2499 (2011).
  39. Itoh, S.; Li, C.; Yamada, M.; Akama, M.; Shimakawa, Y.; Kondo, Y.; Hamada, F. "Selective Extraction Ability of Thiacalix[6]arene Derivatives from Rare Metal Mixed Solution", International Journal of the Society of Materials Engineering for Resources, Vol. 17, pp. 211−215 (2010).
  40. Yamada, M.; Shimakawa, Y.; Kondo, Y.; Hamada, F. "Thiacalix[4]arene-rubidium assembly: supramolecular architecture based on alkali metal coordination and cation-π interactions", CrystEngComm, Vol. 12, pp. 1311−1315 (2010).
  41. Akimoto, K.; Kondo, Y.; Endo, K.; Yamada, M.; Aoyama, Y.; Hamada, F. "A porous coordination architecture assembled by silver triflate and 9,10-bis(3,5-dicyano-1-phenyl)anthracene and its gas adsorption profile", Tetrahedron Letters, Vol. 49, pp. 7361−7363 (2008).
  42. Yamada, M.; Kondo, Y.; Iki, N.; Kabuto, C.; Hamada, F. "Hydrophobic and metal coordination interacted architecture based on p-tert-butylthiacalix[4]arene-potassium complex and its vapor absorption capability", Tetrahedron Letters, Vol. 49, pp. 3906−3911 (2008).
  43. Yamada, M.; Kondo, Y.; Hamada, F. "The X-Ray Crystal Structures of p-Sulfonatothiacalix[6]arene Inclusion Complexes with Lanthanide Metal Ions (M = Gd, Ho and Er) and Water Molecules", International Journal of the Society of Materials Engineering for Resources, Vol. 15, pp. 50−56 (2008).
  44. Yamada, M.; Kondo, Y.; Hamada, F. "Hydrogen-bonded architecture based on p-sulfonatothiacalix[6]arene complex with dysprosium(III) cations and water molecules", Tetrahedron Letters, Vol. 49, pp. 1790−1794 (2008).
  45. Yamada, M.; Kondo, Y.; Akimoto, K.; Kabuto, C.; Hamada, F. "Supramolecular assembly based on p-sulfonatothiacalix[6]arene with sodium and water molecules", New Journal of Chemistry, Vol. 31, pp. 1874−1877 (2007).
  46. Yamada, M.; Shibayama, A.; Kondo, Y.; Hamada, F. "Selective Extraction of Precious Metal from Automotive Catalyst Residue by Thiacalix[6]arene Derivatives", International Journal of the Society of Materials Engineering for Resources, Vol. 15, pp. 13−15 (2007).

Intellectual property right : Patents: 3 (patent pending: 2)

  1. Yoshihiko Kondo, Chun-bin Li, Manabu Yamada, Fumio Hamada, " RARE METAL EXTRACTANT", PCT/JP2009/052198, WO2009/101926, China Patent: ZL 2009 8 0104567.0, US Patent: 8,500,846 B2.
  2. Fumio Hamada, Manabu Yamada, Yoshihiko Kondo, "CYCLIC COMPOUND-METAL COMPLEX ANALOG HAVING GAS OCCLUDING CAPACITY", Japanese Unexamined Patent Application Publication No. 2008-308470.
  3. Yoshihiko Kondo, Atsushi Shibayama, Fumio Hamada, Manabu Yamada, Mitsuhiro Akama, Takanori Imai, "RARE METAL/PLATINUM-GROUP METAL EXTRACTANT AND METHOD FOR EXTRACTING RARE METALS AND PLATINUM-GROUP METALS", JP Patent: 5145536, US Patent: 8,038,969 B2.

Award

  • 2008 Young Award of The Society of Materials Engineering for Resources of Japan.
  • 2011 Best Paper Award of The Society of Materials Engineering for Resources of Japan.
  • 2013 Best Paper Award of The Seventh International Conference on Materials Engineering for Resources (ICMR 2013 Akita).

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