Papers - DANJO Hiroshi
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Preparation of tricationic tris(pyridylpalladium(II)) metallacyclophane as an anion receptor Reviewed
Hiroshi Danjo, Kohei Asai, Tomoya Tanaka, Daiki Ono, Masatoshi Kawahata, Satoshi Iwatsuki
Chemical Communications 58 2196 - 2199 2022.1
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Preparation of cage-shaped hexakis(spiroborate)s Reviewed
Hiroshi Danjo, Yuhki Masuda, Yuki Kidena, Masatoshi Kawahata, Kazuaki Ohara, Kentaro Yamaguchi
Organic & Biomolecular Chemistry 18 ( 18 ) 3717 - 3723 2020.5
Joint Work
Authorship:Lead author, Corresponding author Publisher:Royal Society of Chemistry (RSC)
<p>Direct construction of anionic hexakis(spiroborate) prismatic cages was realized by the reaction of hexahydroxytriphenylene, bis(dihydroxynaphthalene)s, and boric acid.</p>
DOI: 10.1039/d0ob00518e
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Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization Reviewed
Shoko Kikkawa, Hyuma Masu, Kosuke Katagiri, Misaki Okayasu, Kentaro Yamaguchi, Hiroshi Danjo, Masatoshi Kawahata, Masahide Tominaga, Yoshihisa Sei, Hidemasa Hikawa, Isao Azumaya
Cryst. Growth Des. 19 ( 19 ) 2936 - 2946 2019.4
Joint Work
Copyright © 2019 American Chemical Society. N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.
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Construction and structural analysis of mono- and heterobimetallic bis(titanate) molecular cages Reviewed
Toshi Nakagawa, Hiroshi Danjo, Masatoshi Kawahata, Kentaro Yamaguchi
Tetrahedron 75 ( 75 ) 315 - 323 2018.12
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Proton-Induced Assembly-Disassembly Modulation of Spiroborate Twin-Bowl Polymers Bearing Pyridyl Groups Reviewed
Hiroshi Danjo, Masahiro Hamaguchi, Kohei Asai, Mizuki Nakatani, Hiroko Kawanishi, Masatoshi Kawahata, Kentaro Yamaguchi
MACROMOLECULES 50 ( 50 ) 8028 - 8032 2017.9
Joint Work
Authorship:Lead author, Corresponding author Publisher:AMER CHEMICAL SOC
Twin-bowl-shaped tris-(spiroborate) cyclophanes bearing pyridyl groups have been prepared for the construction of proton-responsive supramolecular polymers. Preparation of the pyridyl twin bowls was carried out by the reaction of 6,6'-(3-pyri dyl)-2,2',3,3'-tetrahydroxy- 1, 1'-binaphthyls and an equimolar amount of boric acid in N,N-dimethylformamide in self-organization manner, as previously reported. The reversible acid/base response of the pyridyl twin bowls was evaluated by the addition of hydrochloric acid and aqueous sodium hydroxide. The assembly disassembly modulation of the supramolecular polymers composed of pyridyl twin bowls and the tricationic iridium-(III) complex was also examined. Dissociation of the supramolecular polymers occurred by the addition of hydrochloric acid, and its reconstruction was realized by the addition of aqueous sodium hydroxide. The opposite behavior was observed when the dianionic palladium-(II) complex was employed as a guest. The addition of acid led to the formation of the aggregate that was dissociated by the addition of base.
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Preparation of Peapod Polymer via the Supramolecular Chain Formation by Tris(spiroborate) Twin Bowl Reviewed
Hiroshi Danjo, Toshi Nakagawa, Akio Morii, Yusuke Muraki, Koichi Sudoh
ACS MACRO LETTERS 6 ( 6 ) 62 - 65 2017.1
Joint Work
Authorship:Lead author, Corresponding author Publisher:AMER CHEMICAL SOC
Successive guest-containing tubular polymer was prepared by the olefin metathesis polymerization of tris(spiroborate) twin bowl after the formation of supra molecular polymer. The cationic iridium(III) complexes were topologically fixed inside the polymer to form a peapod-like structure. The polymer was evaluated by SEC, ICP-AES, and DLS analyses, and string-like structures were found in the AFM observation of the peapod polymer.
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Coordination structure and extraction behavior of a silver ion with N-substituted-9-aza-3,6,12,15-tetrathiaheptadecanes: significant effect of Ph-C-N framework on the extractability Reviewed
Satoshi Iwatsuki, Atsushi Ichiyama, Syogo Tanooka, Mari Toyama, Kosuke Katagiri, Masatoshi Kawahata, Kentaro Yamaguchi, Hiroshi Danjo, Kenji Chayama
DALTON TRANSACTIONS 45 ( 45 ) 12548 - 12558 2016.7
Joint Work
Publisher:ROYAL SOC CHEMISTRY
N-Substituted-9-aza-3,6,12,15-tetrathiaheptadecanes having Ph-C-N frameworks (N-R-ATH; R = benzyl (N-Bn-ATH), 4-nitrobenzyl (N-NO2Bn-ATH), and diphenylmethyl (N-Ph2CH-ATH)) were synthesized, and their Ag(I) complexes were structurally characterized. X-Ray crystal structure analyses of [Ag(N-R-ATH)] (BF4) (R = Bn and Ph2CH) revealed monomeric tetra-S-coordinated complex cation structures without the N-coordination, and a benzene ring of the N-R group covered over the amine nitrogen atom. The precise extraction analyses of a Ag(I) ion with ATH derivatives (L = N-R-ATHs and N-H-ATH) associated with the H-1 NMR analyses of the [Ag(L)](+) complexes in polar and non-polar solvents revealed that the introduction of the N-substituent significantly enhanced the extractability of Ag+, due to the "hydrophobic cover" effect by the Ph-C-N framework in the [Ag(N-R-ATH)]+ complexes.
DOI: 10.1039/C6DT01535B
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Development of New Molecular Recognition Modules Constructed via Reversible Spiroborate Formation Reviewed
Hiroshi Danjo
Journal of Synthetic Organic Chemistry 73 ( 7 ) 713 - 722 2015.7
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Multilayered Inclusion Nanocycles of Anionic Spiroborates Reviewed
Hiroshi Danjo, Yuki Kidena, Masatoshi Kawahata, Hiroyasu Sato, Kosuke Katagiri, Toshifumi Miyazawa, Kentaro Yamaguchi
ORGANIC LETTERS 17 ( 17 ) 2466 - 2469 2015.4
Joint Work
Authorship:Lead author, Corresponding author Publisher:AMER CHEMICAL SOC
Multilayered spiroborate nanocycles were prepared from trisor tetrakis(dihydroxynaphthalene) and tetrahydroxyanthraquinone as pillar and crossbar units via the reversible formation of a spiroborate linkage. The four-layered spiroborate nanocycle recognized two cationic aromatic guests simultaneously and exhibited the ability to forth a supramolecular one-dimensional array by combining with methyl viologen dimer as the ditopic guest.
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Nestable Tetrakis(spiroborate) Nanocycles Reviewed
Hiroshi Danjo, Yuhki Hashimoto, Yuki Kidena, Ayumi Nogamine, Kosuke Katagiri, Masatoshi Kawahata, Toshifumi Miyazawa, Kentaro Yamaguchi
ORGANIC LETTERS 17 ( 17 ) 2154 - 2157 2015.4
Joint Work
Authorship:Lead author, Corresponding author Publisher:AMER CHEMICAL SOC
Multicomponent construction of the tetrakis(spiroborate) anionic nanocycles was achieved by reacting bis(dihydroxynaphthalene)s with tetrahydroxyanthraquinone in the presence of boric acid in a self-organized manner. These nanocycles exhibited selective molecular recognition behavior toward cationic guests such as methyl viologen derivatives. Formation of a supramolecular ring@ring and a guest@ring@ring structure was observed by combining the anionic nanocycle and the vinylogous analog of cyclobis(paraquat-p-phenylene).
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Hiroshi Danjo, Toshi Nakagawa, Kosuke Katagiri, Masatoshi Kawahata, Seiki Yoshigai, Toshifumi Miyazawa, Kentaro Yamaguchi
CRYSTAL GROWTH & DESIGN 15 ( 15 ) 384 - 389 2014.11
Joint Work
Authorship:Lead author, Corresponding author Publisher:AMER CHEMICAL SOC
Lanthanide(III)-containing metallosupramolecular arrays were prepared in the crystalline state simply by mixing trifluoromethanesulfonate salts of yttrium(III), lanthanum(III), europium(III), terbium(III), erbium(III), and ytterbium(III) with a rac-tris(spiroborate) twin bowl in N,N-dimethylformamide (DMF). In the crystal, the lanthanide(III) ion coordinated to eight or nine DMF molecules to form spherical tricationic complexes, and the spiroborate twin bowl iteratively glued the complexes to each other to form one-dimensional arrays that were unidirectionally packed in the crystal. In each case, the array structure was stabilized by many aromatic C-H center dot center dot center dot pi interactions and C-H center dot center dot center dot O hydrogen bonds between the twin bowls and the lanthanide(III) complexes. Among the lanthanide(III) ions, yttrium(III), terbium(III), erbium(III), and ytterbium(III) gave almost the same crystal lattice and packing, whereas a different array structure and crystal packing was observed when lanthanum(III) and europium(III) were used, probably due to the difference of the ionic radii of the lanthanide(III) ions.
DOI: 10.1021/cg5014686
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Toshifumi Miyazawa, Masato Yamamoto, Hiroshi Danjo
MONATSHEFTE FUR CHEMIE 144 ( 9 ) 1351 - 1354 2013.9
Joint Work
Publisher:SPRINGER WIEN
Highly selective acylation of the phenolic hydroxy group can be achieved with (hydroxyalkyl)phenols carrying both alcoholic and phenolic hydroxyls by the use of vinyl carboxylates as acyl donors in the presence of rubidium fluoride.
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Preparation of Tris(spiroorthocarbonate) Cyclophanes as Back to Back Ditopic Hosts Reviewed
Hiroshi Danjo, Kazuhisa Iwaso, Masatoshi Kawahata, Kazuaki Ohara, Toshifumi Miyazawa, Kentaro Yamaguchi
ORGANIC LETTERS 15 ( 9 ) 2164 - 2167 2013.4
Joint Work
Authorship:Lead author, Corresponding author Publisher:AMER CHEMICAL SOC
Twin-bowl-shaped tris(spiroorthocarbonate) cyclophanes were designed and prepared as ditopic hosts for electrically neutral or electron-rich guests. Preparation of the desired cyclophanes was achieved by cyclotrimerization of 2,2',3,3'-tetrahydroxy-1,1'-binaphthyl (THB) via the transesterification of tetraphenyl orthocarbonate or dichlorodiphenoxymethane. In those reactions, bis(spiroorthocarbonate) cyclophane containing two THB units was also formed as the kinetically favored product. The spiroorthocarbonate twin bowl exhibited ditopic molecular recognition toward fullerene C-60 in the crystalline state.
DOI: 10.1021/ol4006882
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Chemoselective acylation of (hydroxyalkyl)phenols catalyzed by Candida antarctica lipase B Reviewed
Toshifumi Miyazawa, Masato Yamamoto, Hiroshi Danjo
BIOTECHNOLOGY LETTERS 35 ( 4 ) 625 - 630 2013.4
Joint Work
Publisher:SPRINGER
Acylation of (hydroxyalkyl)phenols with vinyl esters by lipase B from Candida antarctica proceeded smoothly in a highly chemoselective manner, affording their alkyl esters exclusively or at least predominantly. The enzyme therefore discriminates between an alcoholic hydroxyl from a phenolic hydroxyl in addition to having versatile catalytic abilities for organic synthesis.
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A Crystal Structure of Methanesulfonate Salt of 4-(N-Methyl)pyridinium Boronic Acid Reviewed
Satoshi Iwatsuki, Yuki Kanamitsu, Hidetaka Ohara, Masatoshi Kawahata, Hiroshi Danjo, Koji Ishihara
X-ray Struct. Anal. Online 28 63 - 64 2012.8
Joint Work
The structure of a methanesulfonate salt of 4-(N-methyl)pyridinium boronic acid, [4-(N-Me)PyB(OH)2]CH3SO3·H2O, was determined by X-ray crystallography, and was characterized as: P1, a = 5.6937(16), b = 7.805(2), c = 13.522(3)Å, α = 99.46(3), β = 91.45(3), γ = 108.014(17)°, Z = 2, V = 561.8(2)Å3. In the crystals, the cation and the anion are linked by BOH…O(anion), BOH…O(water), and (water)OH…O(anion) hydrogen bonds to stabilize the 1:1:1-cation:anion:water salt unit.
Other Link: https://www.jstage.jst.go.jp/article/xraystruct/28/0/28_63/_article
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Polymorphism of Aromatic Sulfonamides with Fluorine Groups Reviewed
Sho Terada, Kosuke Katagiri, Hyuma Masu, Hiroshi Danjo, Yoshihisa Se, Masatoshi Kawahata, Masahide Tominaga, Kentaro Yamaguchi, Isao Azumaya
CRYSTAL GROWTH & DESIGN 12 ( 6 ) 2908 - 2916 2012.4
Joint Work
Publisher:AMER CHEMICAL SOC
N-(2-Phenoxyphenyl)benzenesulfonamide (1) and fluorine-substituted N-(2-phenoxyphenyl)benzene sulfonamides (2-5) were designed to examine the effect of a fluorine group in the polymorphism of aromatic sulfonamides. Single-crystal X-ray analysis revealed that those with a fluorine (2-5) afforded polymorphs or pseudopolymorphs while the sulfonamide without fluorine (1) did not. From the differential scanning calorimetry measurements, stable (2a-5a) and metastable (2b-5b) crystalline forms were identified. The sulfonamide 1 formed a dimer through hydrogen bonds (H-bonds), which were aligned into two-dimensional (2D) layers via pi/pi and CH/pi interactions. In 2b, 3b, and 4a, the sulfonamide constructed a dimer through H-bonds, which formed 2D layers via CH/F interactions. The sulfonamides 4 formed a one-dimensional (1D) straight chain via H-bonds, which were arranged into 2D layers via CH/F, CH/O, and CH/pi interactions in 4b. The sulfonamide 5 either formed a dimer through H-bonds, which formed 2D layers via CH/O and pi/pi interactions in 5a, or formed a 1D straight chain via CH/O and pi/pi interactions, which were arranged into 2D layers via F/F and CH/F interactions in 5b. In the pseudopolymorph 5c, the sulfonamide 5 formed a 1D zigzag chain via CH/F interactions and was assembled into 2D layers via pi/pi interactions.
DOI: 10.1021/cg300098q
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Tris(spiroborate)-Type Anionic Nanocycles Reviewed
Hiroshi Danjo, Natsuyo Mitani, Yusuke Muraki, Masatoshi Kawahata, Isao Azumaya, Kentaro Yamaguchi, Toshifumi Miyazawa
CHEMISTRY-AN ASIAN JOURNAL 7 ( 7 ) 1529 - 1532 2012.4
Joint Work
Authorship:Lead author, Corresponding author Publisher:WILEY-V C H VERLAG GMBH
New cyclic tris(spiroborate)s were prepared as molecular recognition modules for nanometer-sized cationic guests. These cyclophanes were simply prepared by treating corresponding bis(2,3-dihydroxynaphthalene)s with an equimolar amount of boric acid. The molecular recognition ability of these cyclic spiroborates was estimated in solution and crystal phases by the use of [Ir(tpy2)]3+ as a typical example of a cationic guest.
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Polymorphism of Aromatic Sulfonamides with Fluorine Groups
Terada, S, Katagiri, K, Masu, H, Danjo, H, Kawahata, M, Tominaga, M, Yamaguchi, K, Azumaya, I
RSC Adv. 2 4359 - 4363 2012
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A crystal structure of methanesulfonate salt of 3-(N-methyl)pyridinium boronic acid Reviewed
Satoshi Iwatsuki, Yuki Kanamitsu, Hiroshi Danjo, Koji Ishihara
X-ray Structure Analysis Online 27 ( 10 ) 61 - 62 2011.10
Joint Work
Publisher:Japan Society for Analytical Chemistry
The structure of methanesulfonate salt of 3-(N-methyl)pyridinium boronic acid, [3-(N-Me)PyB(OH)2]CH3SO3, was determined by X-ray crystallography. The boronic acid salt existed in crystals as a monomeric form with a pair of strong O-H...O-S hydrogen bonds, and was characterized as: P21/c, a = 8.9460(18), b = 8.8380(18), c = 13.850(3)Å, β = 105.28(3)°, Z = 4, V = 1056.3(4)Å3. © 2011 The Japan Society for Analytical Chemistry.
Other Link: https://www.jstage.jst.go.jp/article/xraystruct/27/0/27_0_61/_article
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Assembly Modulation by Adjusting Countercharges of Heterobimetallic Supramolecular Polymers Composed of Tris(spiroborate) Twin Bowls Reviewed
Hiroshi Danjo, Kadzuya Hirata, Masanori Noda, Susumu Uchiyama, Kiichi Fukui, Masatoshi Kawahata, Isao Azumaya, Kentaro Yamaguchi, Toshifumi Miyazawa
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 132 ( 44 ) 15556 - 15558 2010.10
Joint Work
Authorship:Lead author, Corresponding author Publisher:AMER CHEMICAL SOC
Heterobimetallic supramolecular polymers were prepared by treatment of the supramolecular polymers composed of tris(spiroborate) type molecular connecting modules with a potassium cation. On the other hand, the addition of a barium cation led to dissociation of the supramolecular polymer chain. Modulation of polymer formation was realized by the use of small metal cations as a control factor.
DOI: 10.1021/ja1084964