Research Topic

Synthesis and assembly of organic/inorganic molecular composites bearing non-symmetric and/or non-linear single molecule electronic properties

Research Aim

We will perform molecular design (in collaboration with the Yoshihiro Asai Group) and synthesis in order to use single molecules to realize functional units (such as rectification, negative differential resistance, memory effect, and integrate-and-fire elements) that can be expected to express new functions through high-order integration. We will demonstrate (in collaboration with the Kazuhiko Matsumoto Group and the Hasegawa Group), using multi-probe measurements using materials such as carbon nanotube electrodes, the high functional expression created by measuring (in collaboration with Tada Group) and integrating the electrical properties of these single molecules. We will also design and synthesize molecular structures for realizing functions based on proposals from other teams. Finally, we will explore the possibility of new information processing methods by combining the molecular structures through collaboration with the Tetsuya Asai Group. So far, we have demonstrated that characteristics like rectification, negative differentiating resistance, or single chain magnets can be realized in a single or small number of molecules by using materials such as porphyrin, imide, polyoxometalate, and carbon nanotubes. We also researched the structuring of functional units through organic synthesis or self-assembly. Based on our findings, our goal is to realize single molecules possessing advanced functions, such as memory effects or integrate-and-fire elements and then to unify these as a step toward brain-like information processing that uses fluctuation.

Role and Need in the Group

This research topic requires the resolution of an extremely broad range of scientific problems, including the physics of a single molecule, the integration and measurement of single-molecule elements, and the emergence of advanced electronic functions through integration, and cannot be addressed through individual research such as that covered by the Grant-in-Aid for Scientific Research. Therefore, we plan to conduct research jointly: with theoretical groups such as the Yoshihiro Asai group during the molecular design stage; the Tada, Matsumoto, and Hasegawa Groups during the measurement stage; and the Tetsuya Asai Groups for the realization of advanced electronic functions through integration. This plan will be accomplished with organic combination of joint research in these areas.

Research Content

(1) Reveal the design guidelines for achieving non-linear and asymmetric electronic functions of single-molecules such as rectification, negative differential resistance, memory effect, and integrate-and-fire elements. This will be accomplished though the mechanical break junction method, the point contact current image atomic force microscope (PCI-AFM) bound to single-walled carbon nanotubes (SWNT), and 2-probe conductive AFM. The group of molecules shown in Figure 4 (mostly synthesized) reveals single-molecule electrical characteristics. Synthesize SWNT and a new polyoxometalate (POM) molecule that can be connected to a metal electrode with a covalent bond, and investigate the relationship between the negative differential resistance and structure at the single-molecule level. (2) Combine three electrodes into a single molecule and consider whether signal amplification is possible. The molecule shown in Figure 5 is an acceptor-donor-acceptor molecule. We combine each of these with SWNTs and perform measurements using multi-probe STMs. We are planning to use SWNTs to isolate metal objects with the same (n, m) index. This will be the first time in the world realizing the three-terminal single-molecule measurement. (3) Investigate the non-linear, asymmetric electronic functions realized in (1), conduct a three-terminal measurement of (2), and consider the expression of new functions, such as a stochastic resonance gate together with the A04 group. (4) Consider, together with the A04 group, what elementary functions are required for realizing higher order functions (such as memory, learning, and judgment, and other brain-like information processing functions that use fluctuation), explore how to achieve these functions with molecules, and then perform the synthesis with the necessary molecular design.Synthesis and assembly of organic.png



Research representative: Takuji Ogawa Professor / Osaka University Graduate School of Science
Member of the research project: Hirofumi Tanaka Professor / Kyushu Institute of Technology Graduate School of Life Science and Systems Engineering
Member of the research project: Daisuke Tanaka /
Member of the research project: Yosuke Tani / Osaka University Graduate School of Science

Papers List


[38] Stable Singlet Biradicals of Rare-Earth-Fused Diporphyrin-Triple-Decker Complexes Having Low Energy Gaps and Multi-Redox States

Sunri Lee; Ken-ichi Yamashita; Naoya Sakata; Yasukazu Hirao; Kaya Ogawa; Takuji Ogawa
Chemistry - A European Journal, , 2018/accepted on 27th December
DOI: 10.1002/chem.201805927

[37] Identification of Tobacco Types and Cigarette Brands Using an Electronic Nose Based on Conductive Polymer/Porphyrin Composite Sensors

C. Henrique A. Esteves; Bernardo A. Iglesias; Takuji Ogawa; Koiti Araki; Lucelia Hoehne; Jonas Gruber
ACS Omega, 3, 6, 6476 - 6482, 2018/6/18(web)
DOI: 10.1021/acsomega.8b00403.

[36] Assignment of Absolute-Handedness Chirality of Single-Walled Carbon Nanotubes using Organic Molecule Supramolecular Structures

Ahmed I. A. Abd El-Mageed; Murni Handayani; Zhijin Chen; Tomoko Inose; Takuji Ogawa
Chemistry - A European Journal, in press, , 2018/accepted on 5th November
DOI: 10.1002/chem.201804832.

[35] Facile preparation of hybrid thin films composed of spin-crossover nanoparticles and carbon nanotubes for electrical memory devices

Daisuke Tanaka; Naoki Aketa; Hirofumi Tanaka; Satoshi Horike; Minoru Fukumori; Takashi Tamaki; Tomoko Inose; Tomoki Akai; Hirotaka Toyama; Osami Sakata; Hiroo Tajiri; Takuji Ogawa
Dalton Transactions, in press, , 2018
DOI: 10.1039/C8DT02923G

[34] Coordination Structure Conversion of Protonated Bisporphyrinato Terbium(III) Double-Decker Complexes and Creation of a Kondo Assembly by Electron Injection on Au(111) Surface

Tomoko Inose; Daisuke Tanaka; Jie Liu; Mizu Kajihara; Puneet Mishra; Takuji Ogawa; Tadahiro Komeda
Nanoscale, 10, 19409 - 19417, 2018/09
DOI: 10.1039/C8NR04630A

[33] Metal ion effect on the supramolecular structures of metalloporphyrins on single-walled carbon nanotube surface

Ahmed I. A. Abd El-Mageed; Takuji Ogawa
Applied Surface Science, 462, 904 - 912, 2018/8
DOI: 10.1016/j.apsusc.2018.08.177

[32] A molecular neuromorphic network device consisting of single-walled carbon nanotubes complexed with polyoxometalate [重要文献]

Hirofumi Tanaka; Megumi Akai-Kasaya; Amin TermehYousefi; Liu Hong; Lingxiang Fu; Hakaru Tamukoh; Daisuke Tanaka; Tetsuya Asai; Takuji Ogawa
Nature Communications, 9, 2693, 2018/7/12
DOI: 10.1038/s41467-018-04886-2

[31] Effects of Radical Initiators, Polymerization Inhibitors, and Other Agents on the Sonochemical Unzipping of Double-Walled Carbon Nanotubes

Minoru Fukumori; Shinnosuke Hara; Takuji Ogawa; Hirofumi Tanaka
Japanese Journal of Applied Physics, 57, 03ED01, , 2018/2/9

[30] Redox-Driven Symmetry Change for Terbium(III) Bis(porphyrinato) Double-Decker Complexes by the Azimuthal Rotation of the Porphyrin Macrocycles [重要文献]

Ken-ichi Yamashita; Takayo Yamanaka; Naoya Sakata; Takuji Ogawa
Chemistry - An Asian Journal, 13, 13, 1692 - 1698, 2018
DOI: 10.1002/asia.201800324


[29] Molecular Design for Single-Molecule Magnetism of Lanthanide Complexes [重要文献]

Sunri Lee; Takuji Ogawa
Chemistry Letters, 46, 1, 10 - 18, 2017
DOI: 10.1246/cl.160800

[28] Fused-Porphyrin Terbium Complexes:Correlations Between Electronic Structure and Single-Molecule Magnetic Property

Sunri Lee; Ken-ichi Yamashita; Satoshi Yamashita; Kaya Ogawa; Yasukazu Hirao; Naoya Sakata; Naoto Ishikawa; Takuji Ogawa
The Electrochemical Society, MA2017-01, 899, 2017

[27] Room-temperature discrete-charge-fluctuation dynamics of a single molecule adsorbed on a carbon nanotube

Agung Setiadi; Hayato Fujii; Seiya Kasai; Ken-ichi Yamashita; Takuji Ogawa; Takashi Ikuta; Yasushi Kanai; Kazuhiko Matsumoto; Yuji Kuwahara; Megumi Akai-Kasaya
Nanoscale, 9, 10674 - 10683, 2017
DOI: 10.1039/C7NR02534C

[26] Non-linear and non-symmetric single-molecule electric properties towards molecular information processing

Takashi Tamaki; Takuji Ogawa
Topics in Current Chemistry, 375, 79 - (29), 2017
DOI: 10.1007/s41061-017-0167-y

[25] Analysis of single molecule conductance of heterogeneous porphyrin arrays by partial transmission probabilities [重要文献]

Takashi Tamaki; Tatsuhiko Ohto; Ryo Yamada; Hirokazu Tada; Takuji Ogawa
ChemistrySelect(Cover Picture), 2, 25, 7484 - 7488 , 2017/08
DOI: 10.1002/slct.201701015

[24] Design and Syntheses of Molecules for Nonlinear and Nonsymmetric Single-Molecule Electric Properties [重要文献]

Takuji Ogawa; Murni Handayani
Molecular Architectonics - The Third Stage of Single Molecule Electronics, 419 - 437, 2017

[23] Oxygen reduction reaction activity in phenol substituted linear Fe(III)-porphyrin dimer

Go Tei; Takashi Tamaki; Takao Hayashi; Kosuke Nakajima; Akihiro Sakai; Satoshi Yotsuhashi; Takuji Ogawa
European Journal of Inorganic Chemistry, 3229 - 3232, 2017
DOI: 10.1002/ejic.201700394

[22] Diameter dependence of longitudinal unzipping of single-walled carbon nanotube to obtain graphene nanoribbon

Minoru Fukumori; Pandey Reetu Raj; Taizo Fujiwara; Amin TermehYousefi; Ryota Negishi; Yoshihiro Kobayashi; Hirofumi Tanaka; Takuji Ogawa
Japanese Journal of Applied Physics, 56, 6S1, , 2017/05
DOI: 10.7567/JJAP.56.06GG12

[21] Dualism of sensitivity and selectivity of porphyrin dimers in electroanalysis

Grzegorz Lisak; Takashi Tamaki; Takuji Ogawa
Analytical Chemistry, 89, 3943 - 3951, 2017
DOI: 10.1021/acs.analchem.6b04179

[20] Synthesis of very narrow multilayer graphene nanoribbon with turbostratic stacking

R. Negishi; K. Yamanoto; H. Kitakawa; M. Fukumori; H. Tanaka; T. Ogawa; Y. Kobayashi
Applied Physics Letters, 110, 201901 - 4, 2017
DOI: 10.1063/1.4983349

[19] Tuning the electrical property of single layer graphene nanoribbon by adsorption of planar molecular nanoparticles

Reetu Raj Pandey; Minoru Fukumori; Amin Termeh Yousefi; Masanori Eguchi; Daisuke Tanaka; Takuji Ogawa; Hirofumi Tanaka
Nanotechnology, 28, 175704, 2017
DOI: 10.1088/1361-6528/aa6567


[18] Non-Symmetric Single-Molecule Electric Properties towards Stochastic Molecular Computation

Takuji Ogawa
International Journal of Parallel, Emergent and Distributed Systems, 32, 271 - 277, 2016
DOI: 10.1080/17445760.2016.1167208

[17] Systematic Structural Elucidation for the Protonated Form of Rare Earth Bis(porphyrinato) Double-Decker Complexes: Direct Structural Evidence of the Location of the Attached Proton

Ken-ichi Yamashita; Naoya Sakata; Takuji Ogawa
Inorg. Chem., 55, 17, 8935 - 8942, 2016
DOI: 10.1021/acs.inorgchem.6b01442

[16] Coadsorption of TbIII-Porphyrin Double-decker Single-molecule Magnets in a Porous Molecular Network: Toward Controlled Alignment of Single-molecule Magnets on a Carbon Surface

Tomoko Inose; Daisuke Tanaka; Oleksandr Ivasenko; Kazukuni Tahara; Steven De Feyter; Yoshito Tobe; Hirofumi Tanaka; Takuji Ogawa
Chemistry Letters, 45, 286 - 288, 2016
DOI: 10.1246/cl.151040


[15] Real-space characterization of hydroxyphenyl porphyrin derivatives designed for single-molecule devices

Akitoshi Shiotari; Yusuke Ozaki; Shoichi Naruse; Hiroshi Okuyama; Shinichiro Hatta; Tetsuya Aruga; Takashi Tamaki; Takuji Ogawa
RSC Advances, 5, 79152 - 79156, 2015/9/3
DOI: 10.1039/C5RA12123J

[14] Method for Controlling Electrical Properties of Single-Layer Graphene Nanoribbons via Adsorbed Planar Molecular Nanoparticles

Hirofumi Tanaka; Ryo Arima; Minoru Fukumori; Daisuke Tanaka; Ryota Negishi; Yoshihiro Kobayashi; Seiya Kasai; T. K. Yamada; Takuji Ogawa
Scientific Reports, 5, 12341 - 12341, 2015/7/24
DOI: 10.1038/srep12341

[13] Effect of Protonation on the Single-Molecule-Magnet Behavior of a Mixed (Phthalocyaninato)(porphyrinato) Terbium Double-Decker Complex

Daisuke Tanaka; Nobuto Sumitani; Tomoko Inose; Hirofumi Tanaka; Naoto Ishikawa; Takuji Ogawa
Chemistry Letters, 44, 5, 668 - 670, 2015/05
DOI: 10.1246/cl.150034


[12] Syntheses of a series of Zinc(II)/freebase porphyrin dimers and trimers with programmable sequences from a common key molecule [重要文献]

Takashi Tamaki; Takenori Nosaka; Takuji Ogawa
The Journal of Organic Chemistry, 79, 22, 11029 - 11038, 2014/10/23
DOI: 10.1021/jo502046d

[11] Thin films of spin-crossover coordination polymers with large thermal hysteresis loops prepared by nanoparticle spin coating

Daisuke Tanaka; Naoki Aketa; Hirofumi Tanaka; Takashi Tamaki; Tomoko Inose; Tomoki Akai; Hirotaka Toyama; Osami Sakata; Hiroo Tajiri; Takuji Ogawa
Chemical Communications, 50, 10074 - 10077, 2014/7/10
DOI: 10.1039/C4CC04123B

[10] Switching of single-molecule magnetic properties and observation of carbon-surface supramolecular structures of Tb(III) porphyrin double-decker complexes [重要文献]

Tomoko Inose; Daisuke Tanaka; Hirofumi Tanaka; Oleksandr Ivasenko; Toshi Nagata; Yusuke Ohta; Steven De Feyter; Naoto Ishikawa; Takuji Ogawa
Chemistry –A European Journal (Cover Picture), 20, 36, 11362 - 11369, 2014/7/7
DOI: 10.1002/chem.201402669

[9] Sequential Phase Transition during Fabricating β-Ag2S Film on Ag Electrode by Wet Chemical Process

Hirofumi Tanaka; Tomoki Akai; Daisuke Tanaka; Takuji Ogawa
e-Journal of Surface Science and Nanotechnology, 12, 185 - 188, 2014/4/26
DOI: 10.1380/ejssnt.2014.185

[8] Design and Synthesis of Perpendicularly Connected Metal Porphyrin-imide Dyads for Two-terminal Wired Single Molecular Diodes [重要文献]

Murni Handayani; Syun Gohda; Daisuke Tanaka; Takuji Ogawa
Chemistry –A European Journal, 20, 25, 7655 - 7664, 2014/5/23
DOI: 10.1002/chem.201402052

[7] Surface self-assembly of trans-substituted porphyrin double-decker complexes exhibiting slow magnetic relaxation

D. Tanaka; T. Inose; S. Shimono; H. Tanaka; T. Tamaki; A. I. A. Abd El-Mageed; A. K. F. Dyab; N. Ishikawa; T. Ogawa
e-Journal of Surface Science and Nanotechnology, 12, 124 - 128, 2014/3/24
DOI: 10.1380/ejssnt.2014.124


[6] New composite porphyrin-conductive polymer gas sensors for application in electronic noses

Carlos H.A. Esteves; Bernardo A. Iglesias; Rosamaria W.C. Li; Takuji Ogawa; Koiti Araki; Jonas Gruber
Sensors & Actuators: B. Chemical, 193, 136 - 141, 2013/11
DOI: 10.1016/j.snb.2013.11.022

[5] Influence of atmosphere on photo-assisted atomic switch operations

T. Hino; T. Hasegawa; H. Tanaka; T. Tsuruoka; *T. Ogawa; M. Aono
Key Eng. Mater., 596, 116 - 120, 2013/12
DOI: 10.4028/

[4] Temperature-dependent current-voltage and photoresponsive properties for semiconducting nanodevices fabricated from an oligothiazole dithiol and gold nanoparticles

T. Tao ; J. Geng; L. Hong; W. Huang; H. Tanaka; D. Tanaka; *T. Ogawa
J. Phys. Chem. C, 117, 48, 25325 - 25333, 2013/11/11
DOI: 10.1021/jp409124u

[3] Volatile and nonvolatile selective switching of a photo-assisted initialized atomic switch

T. Hino; T. Hasegawa; H. Tanaka; T. Tsuruoka; *T. Ogawa; M. Aono
Nanotechnology,, 24, 38, 384006 - 384013, 2013/9/2
DOI: 10.1088/0957-4484/24/38/384006

[2] Advanced Photoassisted Atomic Switch Produced Using ITO Nanowire Electrodes and Molten Photoconductive Organic Semiconductor

A. Klamchuen; H. Tanaka; D. Tanaka; H. Toyama; G. Meng; S. Rahong; K. Nagashima; M. Kanai; T. Yanagida; T. Kawai; T. Ogawa
Advanced Materials, 25, 41, 5893 - 5897, 2013/8/13
DOI: 10.1002/adma.201302552


[1] Rectification direction inversion in a phosphododecamolybdic acid / single-walled carbon nanotube junction,

L. Hong; H. Tanaka; *T. Ogawa
J. Mater. Chem. C, 1, 1137 - 1143, 2012/11/29
DOI: 10.1039/C2TC00171C