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author:("Gotoh, kazusa")
1.  An Extended Phenacene-type Molecule, [8]Phenacene: Synthesis and Transistor Application 
Scientific Reports  2014;4:5330.
A new phenacene-type molecule, [8]phenacene, which is an extended zigzag chain of coplanar fused benzene rings, has been synthesised for use in an organic field-effect transistor (FET). The molecule consists of a phenacene core of eight benzene rings, which has a lengthy π-conjugated system. The structure was verified by elemental analysis, solid-state NMR, X-ray diffraction (XRD) pattern, absorption spectrum and photoelectron yield spectroscopy (PYS). This type of molecule is quite interesting, not only as pure chemistry but also for its potential electronics applications. Here we report the physical properties of [8]phenacene and its FET application. An [8]phenacene thin-film FET fabricated with an SiO2 gate dielectric showed clear p-channel characteristics. The highest μ achieved in an [8]phenacene thin-film FET with an SiO2 gate dielectric is 1.74 cm2 V−1 s−1, demonstrating excellent FET characteristics; the average μ was evaluated as 1.2(3) cm2 V−1 s−1. The μ value in the [8]phenacene electric-double-layer FET reached 16.4 cm2 V−1 s−1, which is the highest reported in EDL FETs based on phenacene-type molecules; the average μ was evaluated as 8(5) cm2 V−1 s−1. The μ values recorded in this study show that [8]phenacene is a promising molecule for transistor applications.
doi:10.1038/srep05330
PMCID: PMC4060465  PMID: 24936854
2.  Bis(4-meth­oxy-3,4-di­hydro­quinazolin-1-ium) chloranilate 
In the title compound [systematic name: bis­(4-meth­oxy-3,4-di­hydro­quinazolin-1-ium) 2,5-di­chloro-3,6-dioxo­cyclo­hexa-1,4-diene-1,4-diolate], 2C9H11N2O+·C6Cl2O4 2−, the chloranil­ate anion lies about an inversion center. The 4-meth­oxy-3,4-di­hydro­quinazolin-1-ium cations are linked on both sides of the anion via bifurcated N—H⋯(O,O) and weak C—H⋯O hydrogen bonds, giving a centrosymmetric 2:1 aggregate. The 2:1 aggregates are linked by another N—H⋯O hydrogen bond into a tape running along [1-10]. The tapes are further linked by a C—H⋯O hydrogen bond into a layer parallel to the ab plane.
doi:10.1107/S1600536813023635
PMCID: PMC3884394  PMID: 24427103
3.  Bis(tri­ethyl­ammonium) chloranilate 
In the crystal structure of the title compound [systematic name: bis­(tri­ethyl­ammonium) 2,5-di­chloro-3,6-dioxo­cyclo­hexa-1,4-diene-1,4-diolate], 2C6H16N+·C6Cl2O4 2−, the chloranilate anion lies on an inversion center. The tri­ethyl­ammonium cations are linked on both sides of the anion via bifurcated N—H⋯(O,O) and weak C—H⋯O hydrogen bonds to give a centrosymmetric 2:1 aggregate. The 2:1 aggregates are further linked by C—H⋯O hydrogen bonds into a zigzag chain running along [01-1].
doi:10.1107/S1600536813021405
PMCID: PMC3884448  PMID: 24427039
4.  A triclinic polymorph of 4-cyano­pyridinium hydrogen chloranilate 
The asymmetric unit of the triclinic polymorph of the title compound (systematic name: 4-cyano­pyridinium 2,5-dichloro-4-hy­droxy-3,6-dioxocyclo­hexa-1,4-dien-1-olate), C6H5N2 +·C6HCl2O4 −, consists of two crystallographically independent cation–anion units, in each of which the cation and the anion are linked by an N—H⋯O hydrogen bond. In the units, the dihedral angles between the cation and anion rings are 78.43 (11) and 80.71 (11)°. In the crystal, each unit independently forms a chain through N—H⋯O and O—H⋯N hydrogen bonds; one chain runs along the c axis while the other runs along [011]. Weak C—H⋯O, C—H⋯N and C—H⋯Cl inter­actions are observed between the chains.
doi:10.1107/S1600536812037221
PMCID: PMC3470192  PMID: 23125636
5.  Morpholinium hydrogen chloranilate methanol monosolvate 
In the crystal structure of the title compound, C4H10NO+·C6HCl2O4 −·CH4O, the components are held together by bifurcated O—H⋯(O,O), O—H⋯(O,Cl) and N—H⋯(O,O) hydrogen bonds into a centrosymmetric 2+2+2 aggregate. The aggregates are further connected by another bifurcated N—H⋯(O, O) hydrogen bond, forming a double-tape structure along the b axis. A weak C—H⋯O inter­action is observed between the tapes.
doi:10.1107/S1600536811047891
PMCID: PMC3238982  PMID: 22199831
6.  4-Chloro-2-nitro­benzoic acid–pyrazine (2/1) 
In the title co-crystal, 2C7H4ClNO4·C4H4N2, the pyrazine mol­ecule is located on an inversion centre, so that the asymmetric unit consists of one mol­ecule of 4-chloro-2-nitro­benzoic acid and a half-mol­ecule of pyrazine. The components are connected by O—H⋯N and C—H⋯O hydrogen bonds, forming a 2:1 unit. In the hydrogen-bonded unit, the dihedral angle between the pyrazine ring and the benzene ring of the benzoic acid is 16.55 (4)°. The units are linked by inter­molecular C—H⋯O hydrogen bonds, forming a sheet structure parallel to (04). A C—H⋯O hydrogen-bond linkage is also observed between these sheets.
doi:10.1107/S1600536811046113
PMCID: PMC3238884  PMID: 22199737
7.  2-Chloro-4-nitro­benzoic acid–quinoline (1/1) 
In the title compound, C7H4ClNO4·C9H7N, the two components are connected by an O—H⋯N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of benzoic acid is 3.15 (7)°. In the crystal, units are linked by inter­molecular C—H⋯O hydrogen bonds, forming a tape along the c axis. The tapes are stacked along the b axis through a C—H⋯O hydrogen bond into a layer parallel to the bc plane.
doi:10.1107/S160053681104075X
PMCID: PMC3247614  PMID: 22219919
8.  2-[4-(2-Formyl­phen­oxy)­but­oxy]­benzaldehyde 
In the crystal structure of the title compound, C18H18O4, the full mol­ecule is generated by the application of an inversion centre. The mol­ecule is essentially planar, with an r.m.s. deviation of 0.017 (1) Å for all non-H atoms. The mol­ecules are linked through inter­molecular C—H⋯O inter­actions to form a mol­ecular sheet parallel to the (02) plane.
doi:10.1107/S1600536811034210
PMCID: PMC3200719  PMID: 22065699
9.  Two solid phases of pyrimidin-1-ium hydrogen chloranilate monohydrate determined at 225 and 120 K 
The crystal structures of two solid phases of the title compound, C4H5N2 +·C6HCl2O4 −·H2O, have been determined at 225 and 120 K. In the high-temperature phase, stable above 198 K, the transition temperature of which has been determined by 35Cl nuclear quadrupole resonance and differential thermal analysis measurements, the three components are held together by O—H⋯O, N⋯H⋯O, C—H⋯O and C—H⋯Cl hydrogen bonds, forming a centrosymmetric 2+2+2 aggregate. In the N⋯H⋯O hydrogen bond formed between the pyrimidin-1-ium cation and the water mol­ecule, the H atom is disordered over two positions, resulting in two states, viz. pyrimidin-1-ium–water and pyrimidine–oxonium. In the low-temperature phase, the title compound crystallizes in the same monoclinic space group and has a similar mol­ecular packing, but the 2+2+2 aggregate loses the centrosymmetry, resulting in a doubling of the unit cell and two crystallographically independent mol­ecules for each component in the asymmetric unit. The H atom in one N⋯H⋯O hydrogen bond between the pyrimidin-1-ium cation and the water mol­ecule is disordered, while the H atom in the other hydrogen bond is found to be ordered at the N-atom site with a long N—H distance [1.10 (3) Å].
doi:10.1107/S010827011000363X
PMCID: PMC2855571  PMID: 20203406
10.  Triethyl­ammonium hydrogen chloranilate 
In the crystal structure of the title compound (systematic name: triethyl­ammonium 2,5-dichloro-4-hy­droxy-3,6-dioxo­cyclo­hexa-1,4-dien-1-olate), C6H16N+·C6HCl2O4 −, two hydrogen chloranilate anions are connected by a pair of bifurcated O—H⋯O hydrogen bonds into a dimeric unit. The triethyl­ammonium cations are linked on both sides of the dimer via bifurcated N—H⋯O hydrogen bonds into a centrosymmetric 2:2 aggregate. The 2:2 aggregates are further linked by inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536810047744
PMCID: PMC3011634  PMID: 21589539
11.  4-Chloro­benzoic acid–quinoline (1/1) 
In the title compound, C7H5ClO2·C9H7N, the 4-chloro­benzoic acid mol­ecule is almost planar, with a dihedral angle of 2.9 (14)° between the carb­oxy group and the benzene ring. In the crystal, the two components are connected by an O—H⋯N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of the benzoic acid is 44.75 (4)°. The two components are further linked by inter­molecular C—H⋯O hydrogen bonds, forming a layer parallel to the ab plane.
doi:10.1107/S1600536810046416
PMCID: PMC3011561  PMID: 21589484
12.  Bis[(3-chloro­benz­yl)ammonium] 2-phenyl­propane­dioate dihydrate 
In the asymmetric unit of the title compound, 2C7H9ClN+·C9H6O4 2−·2H2O, there are two crystallographically independent cations, one dianion and two water mol­ecules. The dihedral angle between the two carboxyl­ate groups of the dianion is 78.1 (2)°. In the crystal, the components are held together by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, forming a layer parallel to the bc plane, with the hydro­philic and hydro­phobic groups located in the inner and outer regions of the layers, respectively.
doi:10.1107/S1600536810029764
PMCID: PMC3007429  PMID: 21588449
13.  3-Hydroxy­pyridinium hydrogen chloranilate monohydrate 
In the title salt hydrate, C5H6NO+·C6HCl2O4 −·H2O, the three components are held together by O—H⋯O and N—H⋯O hydrogen bonds, as well as by C—H⋯O contacts, forming a double-tape structure along the c axis. Within each tape, the pyridinium ring and the chloranilate ring are almost coplanar, forming a dihedral angle of 2.35 (7)°.
doi:10.1107/S1600536809046844
PMCID: PMC2971853  PMID: 21578790
14.  Pyridine-3-carbonitrile–chloranilic acid–acetonitrile (2/1/2) 
In the crystal structure of the title compound, 2C6H4N2·C6H2Cl2O4·2C2H3N, the two symmetry-related pyridine-3-carbonitrile mol­ecules are linked to either side of a chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydr­oxy-1,4-benzoquinone) mol­ecule via inter­molecular O—H⋯N hydrogen bonds, giving a centrosymmetric 2:1 unit. The dihedral angle between the pyridine ring and the chloranilic acid plane is 26.71 (6)°. In addition, the two acetonitrile mol­ecules are linked to either side of the 2:1 unit through C—H⋯N hydrogen bonds, forming a 2:1:2 aggregate. These 2:1:2 aggregates are further linked by weak inter­molecular C—H⋯N and C—H⋯O hydrogen bonds, forming a tape along the c axis.
doi:10.1107/S1600536809036605
PMCID: PMC2970440  PMID: 21577921
15.  2-Carboxy­pyridinium hydrogen chloranilate 
In the crystal structure of the title salt, C6H6NO2 +·C6HCl2O4 −, the pyridine ring and the mean plane of the hydrogen chloranilate anion form a dihedral angle of 77.40 (8)°. The ionic components are held together by N—H⋯O and O—H⋯O hydrogen bonds, forming a supra­molecular ladder. C—H⋯O inter­actions are also present.
doi:10.1107/S1600536809006412
PMCID: PMC2968548  PMID: 21582266
16.  2-Carboxy­pyridinium hydrogen chloranilate. Corrigendum 
Corrigendum to Acta Cryst. (2005), E61, o4215–o4217.
The title and the chemical names of the paper by Tabuchi, Takahashi, Gotoh, Akashi & Ishida [Acta Cryst. (2005), E61, o4215–o4217] are corrected.
doi:10.1107/S1600536809004528
PMCID: PMC2968574  PMID: 21582029
17.  4-Bromo-N-(3,4,5-trimethoxy­benzyl­idene)aniline 
The title compound, C16H16BrNO3, adopts an E configuration with respect to the imine C=N bond. The two benzene rings are twisted with respect to each other at an angle of 38.3 (1)°. In the crystal structure, mol­ecules are connected by weak bifurcated C—H⋯(O, O) hydrogen bonds, forming a helical chain along the b axis.
doi:10.1107/S1600536809003432
PMCID: PMC2968382  PMID: 21582021
18.  catena-Poly[[[N,N′-bis­(3-methoxy­benzyl­idene)ethyl­enediamine]copper(I)]-μ-thio­cyanato-κ2 N:S] 
In the cyrstal structure of the title compound, [Cu(NCS)(C18H20N2O2)]n, the CuI atom is coordinated in a distorted tetra­hedral geometry by two imino N atoms from a bidentate chelating Schiff base ligand, and one N and one S atoms from two thio­cyanate anions. The thio­cyanate anion bridges the CuI atoms, forming a zigzag chain along [101]. The Schiff base ligand adopts an E,E configuration and the dihedral angle between the terminal benzene rings is 53.68 (8)°.
doi:10.1107/S1600536808041925
PMCID: PMC2967908  PMID: 21581537
19.  3,4,5-Trimethoxy­benzohydrazidium chloride 
The title compound, C10H15N2O4 +·Cl−, was obtained as an unexpected by-product during the synthesis of 1-[2-(substituted ar­yl)]-3-methyl­pyrazol-5-ones. The hydrazide group is essentially planar, with an r.s.m. deviation of 0.020 (2) Å, and is oriented at a dihedral angle of 30.52 (3)° with respect to the benzene ring. In the crystal structure, the cations and anions are linked through N—H⋯O and N—H⋯Cl hydrogen bonds, forming a mol­ecular tape running along the b axis.
doi:10.1107/S1600536808036301
PMCID: PMC2959913  PMID: 21581311
20.  1,2-Diazinium hydrogen chloranilate 
In the crystal structure of the title compound, C4H5N2 +·C6HCl2O4 −, there are three crystallographically independent 1,2-diazinium cations and hydrogen chloranilate anions. The anions are held together by pairs of O—H⋯O hydrogen bonds to form two types of dimers, one of which is centrosymmetric. The 1,2-diazinium cations are linked on both sides of each dimer via bifurcated N—H⋯O hydrogen bonds to give two kinds of 2–2 cation–anion associations. The 2–2 associations are linked by inter­molecular C—H⋯O and C—H⋯N hydrogen bonds, forming a mol­ecular tape along the [230] direction. The tapes are further connected by C—H⋯O hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536808031978
PMCID: PMC2959702  PMID: 21580959
21.  3-Fluoro-N-(p-tol­yl)benzamide 
In the crystal structure of the title compound, C14H12FNO, the amide –NHCO– mean plane makes dihedral angles of 28.6 (2) and 37.5 (2)° with the mean planes through the fluoro­benzene and methyl­benzene units, respectively. The dihedral angle between the two benzene ring mean planes is 65.69 (10)°. In the crystal structure, mol­ecules are linked through N—H⋯O hydrogen bonds and stack along the b axis.
doi:10.1107/S160053680803225X
PMCID: PMC2959722  PMID: 21580962
22.  4-Chloro-N-o-tolyl­benzamide 
In the mol­ecule of the title compound, C14H12ClNO, the two benzene rings are close to coplanar [dihedral angle = 7.85 (4)°]. The amide N—C=O plane makes dihedral angles of 34.04 (4) and 39.90 (3)°, respectively, with the 4-chloro- and 2-methyl­phenyl rings. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into chains.
doi:10.1107/S1600536808030912
PMCID: PMC2959280  PMID: 21201235
23.  4-Chloro-N-(2-chloro­phen­yl)benzamide 
In the mol­ecular structure of the title compound, C13H9Cl2NO, the amide N—C=O plane makes dihedral angles of 31.53 (8) and 36.23 (8)°, respectively, with the 4-chloro- and 2-chloro­phenyl rings. The dihedral angle between the two benzene rings is 6.25 (8)°. The mol­ecules are stacked in columns along the b axis through inter­molecular N—H⋯O hydrogen bonds. The columns are further connected by weak C—H⋯O hydrogen bonds. The compound is not isomorphous with the fluoro analogue.
doi:10.1107/S1600536808028882
PMCID: PMC2959385  PMID: 21201142
24.  Redetermination of pyridine-4-carbonitrile–chloranilic acid (1/1) at 180 K 
In the crystal structure of the title compound, C6H4N2·C6H2Cl2O4, two chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydr­oxy-1,4-benzoquinone) mol­ecules are connected by O—H⋯O hydrogen bonds to form a dimeric unit. The pyridine-4-carbonitrile mol­ecules are linked on both sides of the dimer via N⋯H⋯O hydrogen bonds to give a centrosymmetric 2:2 complex of pyridine-4-carbonitrile and chloranilic acid. The H atom in the N⋯H⋯O hydrogen bond is disordered over two positions with approximately equal occupancies. The pyridine ring makes a dihedral angle of 61.54 (14)° with the chloranilic acid plane. The 2:2 units are further linked by inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds. This determination presents a siginficantly higher precision crystal structure than the previously published structure [Tomura & Yamasshita (2008 ▶). X-ray Struct. Anal. Online, 24, x31–x32].
doi:10.1107/S1600536808017182
PMCID: PMC2961658  PMID: 21202894

Results 1-24 (24)