津江研究室の研究成果を紹介するページです.著書,解説,原著論文に分けて研究成果を掲載しています.

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著書・解説・論文リスト

1.著書

[1] 京都大学地球環境学研究会(津江ら16名共著),「地球環境学のすすめ」,丸善,94-110頁,2003年.
[2] Tsue, H., Ishibashi, K., Tamura, R. "Azacalixarene: A New Class in the Calixarene Family", In Heterocyclic Supramolecules I, Matsumoto, K. (ed.), Topics in Heterocyclic Chemistry, Vol. 17, Springer-Verlag, pp 73-96, 2008.
[3] 津江広人, 田村類,「基礎環境化学」, サイエンス社, 2009年.
[4] 入江一浩,津江広人,高野俊幸,加納太一,板東俊和,藤田健一,「有機化学要論」,学術図書出版社,1-27頁,2015年.
[5] Tsue, H., Oketani, R. "Azacalixarene: An Ever-Growing Class in the Calixarene Family", In Advances in Organic Crystal Chemistry, Tamura, R, Miyata, M. (eds.), Springer, Chapter 13, in press.

2.解説

[1] 津江広人, 堀口雅弘, 田村類, 藤井孝太郎, 植草秀裕, 「粉末X線回折データを用いる有機化合物の結晶構造解析」, 有機合成化学協会誌, 65巻, 1203-1212頁, 2007年.
[2] 津江広人, 石橋孝一, 田村類, 「アザカリックスアレーンの化学」,有機合成化学協会誌, 67巻, 898-908頁, 2009年.
[3] 津江広人, 「窒素原子を配した大環状化合物が構築する非多孔質有機分子性結晶への気体吸蔵」, 日本結晶学会誌, 55巻, 37-41頁, 2013年.

3.論文

2014年

[1] Highly Efficient Chiral Resolution of DL-Arginine by Cocrystal Formation Followed by Recrystallization under Preferential Enrichment Conditions.
Iwama, S., Kuyama, K., Mori, Y., Manoj, K., Gonnade, R. G., Suzuki, K., Hughes, C. E., Williams, P. A., Harris, K. D. M., Veesler, S., Takahashi, H., Tsue, H., Tamura, R.
Chemistry A European Journal, 20, 10343-10350 (2014).
[2] Crystal Engineering of Homochiral Molecular Organization of Naproxen in Cocrystals and Their Thermal Phase Transformation Studies.
Manoj, K., Tamura, R., Takahashi, H., Tsue, H.
CrystalEngComm, 16, 5811-5819 (2014).
[3] Selective Adsorption of Mercury(II) Ion by p-tert-Butylcalix[4]thiacrown-5 at a Solid-Liquid Interface
Takimoto, T., Tsue, H., Tamura, R., Sasaki, H.
Heterocycles, 90, 842-846 (2014).

2013年

[1] Solid-Gas Sorption Behavior of a New Polymorph of Azacalix[5]arene Pentamethyl Ether as Controlled by Crystal Architecture.
Tsue, H., Ono, K., Tokita, S., Takahashi, H., Tamura, R.
CrystEngComm, 15, 1536-1544 (2013).
[2] Synthesis of p-tert-Butylcalix[4]thiacrowns Exhibiting Sulfur Number-Dependent Complexation with Mercury(II) Ion.
Takimoto, T., Tsue, H., Takahashi, H., Tamura, R., Sasaki, H.
Heterocycles, 88, 911-917 (2013).

2012年

[1] Crystallographic Analysis of CO2 Sorption State in Seemingly Nonporous Molecular Crystal of Azacalix[4]arene Tetramethyl Ether Exhibiting Highly Selective CO2 Uptake.
Tsue, H., Takahashi, H., Ishibashi, K., Inoue, R., Shimizu, S., Takahashi, D., Tamura, R.
CrystEngComm, 14, 1021-1026 (2012).
[2] Occurrence of Spontaneous Resolution of Ketoprofen with a Racemic Crystal Structure by Simple Crystallization under Nonequilibrium Preferential Enrichment Conditions.
Gonnade, R. G., Iwama, S., Sigiwake R., Manoj, K., Takahashi, H., Tsue, H., Tamura, R.
Chemical Communications, 48, 2791-2793 (2012).
[3] Synthesis of p-Chloroazacalix[5]arene Pentamethyl Ether: Ring Size-Dependent Desorption of N-Benzyl Groups.
Tsue, H., Miyata, K., Takahashi, D., Takahashi, H., Sasaki, K., Tamura, R.
Heterocycles, 86, 159-164 (2012).

2011年

[1] Observation of Efficient Preferential Enrichment Phenomenon for a Cocrystal of (DL)-Phenylalanine and Fumaric Acid under Nonequilibrium Crystallization Conditions.
Gonnade, R.G., Iwama, S., Mori, Y., Takahashi, H., Tsue, H., Tamura, R.
Crystal Growth & Design, 11, 607-615 (2011).
[2] Spontaneous and Selective CO2 Sorption under Ambient Conditions in Seemingly Nonporous Molecular Crystal of Azacalix[5]arene Pentamethyl Ether.
Tsue, H., Ono, K., Tokita, S., Ishibashi, K., Matsui, K., Takahashi, H., Miyata, K., Takahashi, D., Tamura, R.
Organic Letters, 13, 490-493 (2011).

2010年

[1] Observation of the Preferential Enrichment Phenomenon for Essential ?-Amino Acids with a Racemic Crystal Structure.
Iwama, S., Horiguchi, M., Sato, H., Uchida, Y., Takahashi, H., Tsue, H., Tamura, R.
Crystal Growth & Design, 10, 2668-2675 (2010).

2009年

[1] Azacalix[4]arene Tetramethyl Ether with Inherent Chirality Generated by Substitution on the Nitrogen Bridges.
Ishibashi, K., H., Tsue, H., Takahashi, H., Tamura, R.
Tetrahedron: Asymmetry, 20, 375-380 (2009).
[2] Relationship between Crystal Polymorphism and Solution Structure of an Imidazopyridine Derivative Developed as a Drug Substance for Osteoporosis.
Hirano, M., Igarashi, K., Machiya, K.; Tamura, R., Tsue, H. Ooshoima, H.
Journal of Chemical Engineering of Japan 42: 204-211 (2009).

2008年

[1] Control of the Mode of Polymorphic Transition Inducing Preferential Enrichment by Modifying the Molecular Structure or Adding Seed Crystals: Significant Influence of CH/F Hydrogen Bonds.
Horiguchi, M., Okuhara, S., Shimano, E., Fujimoto, D., Takahashi, H., Tsue, H., Tamura, R.
Crystal Growth & Design, 8, 540-548 (2008).
[2] Partial Resolution of Racemic trans-4-[5-(4-Alkoxyphenyl)-2,5-dimethylpyrrolidine-1-oxyl-2-yl]benzoic Acids by the Diastereomer Method with (R)- or (S)-1-Phenylethylamine.
Uchida, Y., Uematsu, T., Nakayama, Y., Takahashi, H., Tsue, H., Tanaka, K., Tamura, R.
Chirality, 20, 282-287 (2008).
[3] Azacalix[4]areneCation Radicals: Spin-Delocalised Doublet- and Triplet-Ground States Observed in the Macrocyclicm-Phenylene System Connected with Nitrogen Atoms
Ishibashi,K., Tsue, H., Sakai, N., Tokita, S., Matsui, K., Yamauchi J., and Tamura, R.
Chemical Communications, 2812-2814 (2008).
[4] Case Study on the Effects of Molecular Structures on the Mode of Polymorphic Transition Inducing Preferential Enrichment.
Horiguchi, M., Yabunaka, S., Iwama, S., Shimano, E., Lepp, Z., Takahashi, H., Tsue, H., and Tamura, R.
European Journal of Organic Chemistry, 3496-3505 (2008)
[5] Synthesis, Molecular Structure, and Oxidation Behavior of Exhaustively MethylatedAzacalix[6]arene.
Ishibashi, K., Tsue, H., Takahashi, H., Tokita, S., Matsui, K., Tamura, R.
Heterocycles, 76, 541-500 (2008).
[6] Azacalix[6]arene Hexamethyl Ether: Synthesis, Structure, and Selective Uptake of Carbon Dioxide in the Solid State.
Tsue, H., Ishibashi, K., Tokita, S., Takahashi, H., Matsui, K., Tamura, R.
Chemistry-A European Journal, 14, 6125-6134 (2008).
[7] Enantiomeric Resolution of Racemic C2-Symmetric trans-2,5-Dimethyl-2,5-diphenylpyrrolidine and trans-2,5-Dimethyl-2,5-bis(3-hydroxyphenyl)pyrrolidine by a Diastereomer Method.
Uchida, Y., Nakayama, Y., Suzuki, K., Oki, S., Horiguchi, M., Tsue, H., Tamura, R.
Heterocycles, 76, 875-881 (2008).
[8] Azacalix[7]arene Heptamethyl Ether: Preparation, Nanochannel Crystal Structure, and Selective Adsorption of Carbon Dioxide.
Tsue, H., Matsui, K., Ishibashi, K., Takahashi, H., Tokita, S., Ono, K., Tamura, R.
The Journal of Organic Chemistry, 73, 7748-7755 (2008).

2007年

[1] Mechanistic Flexibility of Solvent-Assisted Solid-to-Solid Polymorphic Transition Causing Preferential Enrichment: Significant Contribution of p/p and CH/p Interactions as Well as hydrogen Bonds.
Horiguchi, M., Okuhara, S., Shimano, E., Fujimoto, D., Takahashi, H., Tsue, H., Tamura, R.
Crystal Growth & Design, 7, 1643-1652 (2007).
[2] Frozen 1,3-Alternate Conformation of Exhaustively Methylated Azacalix[4]arene in Solution: Successful Immobilization by Small but yet Sufficiently Bulky O-Methyl Group.
Tsue, H., Ishibashi, K., Tokita, S., Matsui, K., Takahashi, H., Tamura, R.
Chemistry Letters, 36, 1374-1375 (2007).

2006年

[1] Induction and Inhibition of Preferential Enrichmenr by Controlling the Mode of Polymorphic Transition with Seed Crystals.
Tamura, R., Mizuta, M., Yabunaka, S., Fujimoto, D., Ariga, T., Okuhara, S., Ikuma, N., Takahashi, H., Tsue, H.
Chemistry-A European Journal, 12, 3515-3527 (2006)
[2] Adsorptive Removal of Endocrine Disrupting Chemicals by Calix[4]crown Oligomer: Significant Improvement of Removal Efficiency by Oligomerization.
Tsue, H., Takimoto, T., Kikuchi, C., Yanase, H., Ishibashi, K., Amezawa, K., Miyashita, H., Miyafuji, H., Tanaka, S., Tamura, R.
Chemistry Letters, 35, 254-255 (2006).
[3] Regioselective N-Methylated Azacalix[8]arene Octamethyl Ether Prepared by Catalytic Aryl Amination Reaction Using a Temporal N-Silylation Protocol.
Ishibashi, K., Tsue, H., Tokita, S., Matsui, K., Takahashi, H., Tamura, R.
Organic Letters, 8, 5991-5994 (2006)

2005年

[1] Spontaneous Racemization and Epimerization Behavior in solution of Chiral Nitroxides.
Ikuma, N., Tsue, H., Tsue, N., Shimono, S., Uchida, Y., Masaki, K., Matsuoka, N., Tamura, R.
Organic Letters, 7, 1797-1800 (2005).
[2] Exhausitively Methylated Azacalix[4]arene: Preparation, Conformation, and Crystal Structure with Exclusively CH/π-Controlled Crystal Architecture.
Tsue, H., Ishibashi, K., Takahashi, H., Tamura, R.
Organic Letters, 7, 2165-2168 (2005).
[3] Adsorptive Removal of Bisphenol A by Calix[4]crown Derivatives: Significant Contribution of Hydrogen Bonding Interaction to the Control of Adsorption Behavior.
Tsue, H., Takimoto, T., Kikuchi, C., Yanase, H., Takahashi, H., Amezawa, K., Ishibashi, K., Tanaka, S., Tamura, R.
Chemistry Letters, 34, 1030-1031 (2005).

2004年

[1] Significant Contribution of Phenyl Centroid---I-C(sp2) Coulombic Donor-Acceptor Attraction to the
Buildup of a Crystal Structure.
Takahashi, H., Tamura, R., Yabunaka, S., Mizuta, M., Ikuma, N., Tsue, H., Ushio, T.
Mendeleev Communications, 229-241 (2004).
[2] A Facile Synthesis of Dibenzylated p-tert-Butylcalix[4]crowns under Non-Diluted Reaction Conditions.
Tsue, H.; Takimoto, T.; Tamura, R.; Kikuchi, C.; Tanaka, S.
Letters in Organic Chemistry. 1, 276-279 (2004).