Organoelement Chemistry Institute for Chemical Research, Kyoto University

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ABOUT

We aim to synthesize new molecules, explore the unknown properties of the molecules, and develop the functions that emerge when these molecules are assembled. We aim to develop "Full-Spectrum Chemistry" that can contribute widely to science and technology. We will thoroughly pursue the possibilities of our original organic molecules.

Our strategy is as follows:

  • Precise molecular design using computational science
  • Organic synthesis incorporating state-of-the-art reactions
  • Development of novel skeletons utilizing the characteristics of heteroatoms
  • Structural analysis and spectroscopic characterization using a variety of instruments
  • Bottom-up synthesis of nanocarbon materials and substrate surface-assisted synthesis
  • Orientation control of organic molecules and their application to organic electronic devices

PUBLICATIONS

2024.10.21

Synthesis of π-Extended [1.1]Paracyclophanes, [1.1][n]PCP (n = 2, 3, and 4), and Their Through-space Conjugation
E. Kayahara*, S. Hirata, Y. Mizuhata, Y. Yasuda, Y. Kusakabe, H. Kaji, S. Yamago*
Chem. Eur. J., 2024, 30, e202402225.
DOI: 10.1002/chem.202402225

2024.10.17

Quantitative analysis of air-oxidation reactions of thiolate-protected gold nanoclusters
W. Suzuki, R. Takahata, Y. Mizuhata, N. Tokitoh, S. Xue, T. Teranishi*
Chem. Sci., 2024, in press.
DOI: 10.1039/D4SC02995J

2024.8.28

Synthesis of Hetero-Trimetal Porphyrin Nanobelts
S. Xue*, X. Lv, Y. Dong, T. Zhang, F. Qiu*, J. Pan*, D. Kuzuhara, H. Yamada, N. Aratani*
Chem. Eur. J., 2024, 30, e202402680.
DOI: 10.1002/chem.202402680

2024.8.13

Ethynylene-Bridged Pentacene Trimer and Tetramer Prepared Through Unexpected Oligomerization and Their Subsequent Thermal Conversions
H. Hayashi*, J. Zhu, N. Minamino, Y. Murakami, S. Kasahara, K. Matsuo, N. Aratani, H. Yamada*
Eur. J. Org. Chem., 2024, 30, e202400770.
DOI: 10.1002/ejoc.202400770

2024.8.8

A Unique Synthetic Route toward a 1,2-Dihydrodigermene via Formal α-Elimination of Bromo and Silyl Groups from a Bromo(phenylsilyl)germane
D. Uchida, M. Yukimoto, N. Tokitoh, H. Yamada, Y. Mizuhata*
Z. Anorg. Allg. Chem., 2024, in press.
DOI: 10.1002/zaac.202400131

2024.8.6

Synthesis of π-Ring-Fused Porphyrin(2.1.1.1)s and Their Rh(I) Complexes
Y. Dong, F. Wu, T. Zhang, F. Qiu*, J. Pan, Y. Mizuhata, H. Yamada, T. Teranishi, S. Xue*
Inorg. Chem., 2024, 63, 15510-15515.
DOI: 10.1021/acs.inorgchem.4c02669

2024.7.25

Reaction of potassium germabenzenide with benzil: Unusual ring opening to form a unique polycyclic penta-coordinated germanate
S. Tsuji, N. Tokitoh, H. Yamada, Y. Mizuhata*
Main Gr. Met. Chem., 2024, 47, 20230031.
DOI: 10.1515/mgmc-2023-0031

2024.7.8

Orbital hybridisation of π-conjugated ligands and an atomically precise metal nucleus for two-photon absorption
M. Sakamoto, Y. Mizuhata, W. Ota, T. Konishi, K. Kamata, T. Sato
ChemRxiv, preprint.
DOI: 10.26434/chemrxiv-2024-jx3rr

2024.7.4

Dual-benefit strategy for developing an efficient photodetector with prompt response to UV-near IR radiations: in situ synthesis and crystallization through a simple one-step annealing
M. Yu, Z.-C. Wan, S.-W. Song, Z.-Y. Yang*, M. Suzuki*, H. Yamada*
J. Mat. Chem. A, 2024, 12, 19288-19297.
DOI: 10.1039/D4TA03202K

2024.6.20

Synthesis of N2-Type Superatomic Molecules
R. Saito, K. Isozaki*, Y. Mizuhata, M. Nakamura*
J. Am. Chem. Soc., 2024, 146, 20930-20936.
DOI: 10.1021/jacs.4c05611

2024.6.18

Dioxygen Activation by Gold(I)-Distorted Porphyrin Dinuclear Complexes
W. Suzuki, Y. Mizuhata, N. Tokitoh, T. Teranishi*
Chem. Eur. J., 2024, 30, e202401242.
DOI: 10.1002/chem.202401242

2024.5.31

Bowl-Shaped Kekulene Analogues: Cycloarenes with two Five-Membered Rings
H. Murakami, H. Iwabuchi, M. Asari, H. Yamada, D. Kuzuhara*
Chem. Eur. J., 2024, 30, e202401828.
DOI: 10.1002/chem.202401828

2024.3.6

Self-Assembly Behavior of Perylene Bisimide Derivatives on a Perovskite Nanocrystal Surface
N. Kubo, M. Yamauchi*, H. Yamada, S. Masuo*
J. Phys. Chem. C, 2024, 128, 4648-4654.
DOI: 10.1021/acs.jpcc.3c08420

2024.2.23

On-surface smooth polymerization of 5,11-bianthryl-anthradithiophene
S. Kasahara, M. Ohtomo*, R. Hayashi, N. Fushimi, J. Yamaguchi, K. Matsuo, N. Aratani, S. Sato*, H. Hayashi*, H. Yamada*
Chem. Lett., 2024, 53, upae036.
DOI: 10.1093/chemle/upae036

2024.2.22

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments
A. Okba, P. S. Marqués, K. Matsuo, N. Aratani, H. Yamada, G. Rapenne, C. Kammerer*
Beilstein J. Org. Chem., 2024, 20, 287-305.
DOI: 10.3762/bjoc.20.30

2024.2.14

Enhanced Host-Guest Interaction between [10]Cycloparaphenylene ([10]CPP) and [5]CPP by Cationic Charges
E. Kayahara, Y. Mizuhata, S. Yamago
Beilstein J. Org. Chem., 2024, 20, 436-444.
DOI: 10.3762/bjoc.20.38

2024.2.3

Excellent π-Bowl Semiconductors Based on C70 Subunit
M. Chen, Y. Duan, X. Liu*, Q. Zhan, H. Hayashi*, K. Matsuo, H. Yamada, G. Gao*, Y. Zheng, L. Zhang*
CCS Chem., 2024, 6, 353-364
DOI: 10.31635/ccschem.023.202302848

2023.12.27

Quantitative Analysis of Photochemical Reactions in Pentacene Precursor Films
N. Shioya*, T. Fang, M. Fujii, R. Fujiwara, H. Hayashi, H. Yamada, T. Hasegawa*
Langmuir, 2024, 40, 1137-1142.
DOI: 10.1021/acs.langmuir.3c03594

2023.12.21

Synthesis of 1-Adamantylaminogermylene and Its Chalcogenation Reactions
M. Yukimoto*, K. Kanda, T. Aoki, Y. Mizuhata, N. Tokitoh*
Eur. J. Inorg. Chem., 2024, 27, e202300663.
DOI: 10.1002/ejic.202300663

2023.12.8

Single-Photon Emission from Organic Dye Molecules Adsorbed on a Quantum Dot via Energy Transfer
M. Yoshioka, M. Yamauchi, N. Tamai, S. Masuo*
Nano Lett., 2023, 23(24), 11548–11554.
DOI: 10.1021/acs.nanolett.3c03279

2023.12.4

Potassium 2-Germanaphthalenide: An Isolable Polycyclic System of Germanium-Incorporated Anionic Benzenoid
S. Tsuji, N. Tokitoh, H. Yamada, Y. Mizuhata*
Inorg. Chem. Front., 2024, 11, 400-408.
DOI: 10.1039/D3QI02183A
[Selected as Front Cover]

2023.11.20

One-Dimensionally Arranged Quantum-Dot Superstructures Guided by a Supramolecular Polymer Template
M. Yamauchi*, K. Nakatsukasa, N. Kubo, H. Yamada, S. Masuo*
Angew. Chem. Int. Ed., 2023, 63, e202314329.
DOI: 10.1002/anie.202314329

2023.11.17

The Reduction of Metallabenzenes: Different Scenarios Highly Dependent on the Central Group 14 Elements, Si vs. Ge
S. Tsuji, N. Tokitoh*, H. Yamada, Y. Mizuhata*
Chem. Asian. J., 2023, 19, e202300945.
DOI: 10.1002/asia.202300945
[Selected as Very Important Paper]

2023.11.7

Complexation study of a 1,3-phenylene-bridged cyclic hexa-naphthalene with fullerenes C60 and C70 in solution and 1D-alignment of fullerenes in the crystals
P. Mei, H. Morimoto, Y. Okada, K. Matsuo, H. Hayashi, A. Saeki, H. Yamada*, N. Aratani*
RSC Adv., 2023, 13, 33459.
DOI: 10.1039/d3ra06526j

2023.11.3

Mixed-Ligand Approach to Palladium-Catalyzed Direct Arylation of Heteroarenes with Aryl Chlorides: Controlling Reactivity of Catalytic Intermediates via Dynamic Ligand Exchange
M. Wakioka,* K. Hatakeyama, S. Sakai, T. Seki, K. Tada, Y. Mizuhata, T. Nakazato, S. Koguchi, Y. Shibuya, Y. Maruyama, M. Ayabe
Organometallics, 2023, 42, 3454-3465.
DOI: 10.1021/acs.organomet.3c00409
[Selected as Front Cover]

2023.9.29

An Unsymmetrical 5,15-Disubstituted Tetrabenzoporphyrin: Effect of Molecular Symmetry on the Packing Structure and Charge Transporting Property
K. Miyazaki, K. Matsuo*, H. Hayashi, M. Yamauchi, N. Aratani, H. Yamada*
Org. Lett., 2023, 25, 7354–7358.
DOI: 10.1021/acs.orglett.3c02815

2023.9.26

Small Molecule Activation Based on Novel Heavier Group 13/15 Interelement Compounds, λ3,λ3-Phosphanylalumanes
T. Yanagisawa, Y. Mizuhata, N. Tokitoh*
Bull. Chem. Soc. Jpn., 2023, 97, bcsj.20230186.
DOI: 10.1093/bulcsj/bcsj.20230186

2023.9.25

Recent progress in the chemistry of heavy aromatics
S. Fujimori, Y. Mizuhata, N. Tokitoh*
Proceedings of the Japan Academy, Series B, 2023, 99, 480-512.
DOI: 10.2183/pjab.99.027

2023.8.12

Synthesis and characterization of novel hydrodigermenide and digermyne radical anion
Y. Mizuhata,* W. Ijichi, R. Nishino, T. Kato, E. Kayahara, S. Yamago, N. Tokitoh*
Polyhedron, 2023, 244, 116614.
DOI: 10.1016/j.poly.2023.116614

2023.8.12

A Multiple Stimuli-responsive Supramolecular Organic Framework under Concomitant Emission Color Changes
H. Tanaka, Y. Mizuhata, N. Tokitoh, R. Miyamoto, K. Kanamori, H. Kaji*
J. Phys. Chem. C, 2023, 127, 20459–20465.
DOI: 10.1021/acs.jpcc.3c03459
[Selected as Supplementary Cover]

2023.7.28

Unusual nuclear exchange within a germanium-containing aromatic ring that results in germanium atom transfer
R. Nishino, N. Tokitoh,* R. Sasayama, R. Waterman, Y. Mizuhata*
Nature Commun., 2023, 14, 4519.
DOI: 10.1038/s41467-023-40188-y

2023.7.4

Solid-state Chromism of Zwitterionic Triarylmethylium Salts
K. Iwai, Y. Mizuhata,* T. Nakamura, M. Goto, A. Wakamiya, Y. Shimakawa, N. Tokitoh*
Eur. J. Inorg. Chem., 2023, 31, e202300337.
DOI: 10.1002/ejic.202300337
[Selected as Front Cover]

2023.6.16

Isomer-Selective Conversion of Au Clusters by Au(I)-Thiolate Insertion
Y. Chiga, R. Takahata, W. Suzuki, Y. Mizuhata, N. Tokitoh, T. Teranishi*
Inorg. Chem., 2023, 62, 10049-10053.
DOI: 10.1021/acs.inorgchem.3c01442

2023.5.19

Enhancing NIR-to-visible photon upconversion in cast solid by introducing bulky substituents in rubrene and by suppressing back energy transfer
A. Sawa, S. Shimada, N. Tripathi, C. Heck, H. Tachibana, E. Koyama, T. Mizokuro, Y. Hirao, T. Kubo, N. Tamai, D. Kuzuhara, H. Yamada, K. Kamada*
J. Mat. Chem. C, 2023, 11, 8502-8513.
DOI: 10.1039/D3TC00853C

2023.4.1

Synthesis of polyacene by using a metal-organic framework
T. Kitao, T. Miura, R. Nakayama, Y. Tsutsui, Y. S. Chan, H. Hayashi, H. Yamada, S. Seki, T. Hitosugi, T. Uemura*
Nat. Synth., 2023.
DOI: 10.1038/s44160-023-00310-w

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NEWS

  • 2023/7/3
    Mr. MIYAZAKI, Kazuya (M2) joined to our lab.
  • 2023/7/1
    Dr. YUKIMOTO, Mariko moved to University of Toyama.
  • 2023/6/1
    Assist. Prof. MATSUO, Kyohei joined to our lab.
  • 2023/4/7
    Three new M1's and three new D1's have been assigned. Congratulations on your enrollment! We are starting with a total of 19 members.
  • 2023/4/1
    The Organoelement Chemistry Laboratory has been newly launched.
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