SHIN-ICHIRO KATO@USP

Original Paper

2024

Self-Assembly of Thienopyrrole-Fused Thiadiazoles Containing an Amide Linker: Control of Supramolecular Polymerization Mechanism and Chiroptical Properties by Trialkoxy Side Chains

T. Yamaguchi, Y. Naito, C. Kitamura, H. Takeshita, S. Ida, T. Ishi-i, K. Suzuki, T. Matsumoto, Y. Shiota, D. Suzuki, Y. Imai, T. Ikeda, S.-i. Kato

Chem. Asian J. 2024, 19, e202400829.

DOI: 10.1002/asia.202400829

2023

Isomerism Tunes the Diradical Character of DifluorenoPyrroles at Constant Hückel-Level Antiaromaticity

R. Moriyasu, S. Moles Quintero, C. J. Gomez Garcia, K. Suzuki, C. Kitamura, M. Murata, M. Alonso, J. Casado, S.-i. Kato

Chem. Sci. 2023, 14, 13468-13474.

DOI: 10.1039/D3SC03297C

Site-Selective Radical Reactions of Kinetically Stable Open-Shell Singlet Diradicaloid Difluorenoheteroles with Tributyltin Hydride and Azo-Based Radical Initiators

N. Tabata, T. Uchino, C. Kitamura, K. Yoshizawa, Y. Shiota, S.-i. Kato

Chem. Sci. 2023, 14, 5974-5982.

DOI: 10.1039/D3SC00381G

A Double-Helical S,C-Bridged Tetraphenyl-para-Phenylenediamine and Its Persistent Radical Cation

K. Harada, C. Hasegawa, T. Matsumoto, H. Sugishita, C. Kitamura, S. Higashibayashi, M. Hasegawa, S. Suzuki, S.-i. Kato

Chem. Commun. 2023, 59, 1301-1304.

DOI: 10.1039/D2CC06144A

A Series of Boron Difluoride Complexes of Azinylcarbazoles: Synthesis and Structure–Property Relationships

K. Yamamoto, S. Matsui, S.-i. Kato, Y. Nakamura

Org. Biomol. Chem. 2023, 21, 5398-5405.

DOI: 10.1039/D3OB00795B

2022

Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles

S. Mori, S. Moles Quintero, N. Tabata, R. Kishi, R. Gonzñález Núñez, A. Harbuzaru, R. Ponce Ortiz, J. Marín Beloqui, S. Suzuki, C. Kitamura, C. J. Gómez-García, Y. Dai, F. Negri, M. Nakano, S.-i. Kato, J. Casado

Angew. Chem. Int. Ed. 2022, 61, e202206680.

DOI: 10.1002/anie.202206680

Augmented Self-Association by Electrostatic Forces in Thienopyrrole-Fused Thiadiazoles that Contain an Ester instead of an Ether Linker

Y. Naito, R. Moriguchi, C. Kitamura, T. Matsumoto, T. Yoshihara, T. Ishi-i, Y. Nagata, H. Takeshita, K. Yoshizawa, Y. Shiota, K. Suzuki, S.-i. Kato

Chem. Asian J. 2022, 17, e202101341.

DOI: 10.1002/asia.202101341

2021

S,C,C- and O,C,C-Bridged Triarylamines and Their Persistent Radical Cations

S. Kataoka, S. Suzuki, Y. Shiota, K. Yoshizawa, T. Matsumoto, M. S. Asano, T. Yoshihara, C. Kitamura, S.-i. Kato

J. Org. Chem. 2021, 86, 12559-12568.

DOI: 10.1021/acs.joc.1c00969

Arylene–Hexaynylene and –Octaynylene Macrocycles: Extending the Polyyne Chains Drives Self-Association by Enhanced Dispersion Force

S.-i. Kato, R. Kumagai, T. Abe, C. Higuchi, Y. Shiota, K. Yoshizawa, N. Takahashi, K. Yamamoto, Md Z. Hossain, K. Hayashi, T. Hirose, Y. Nakamura

Chem. Commun. 2021, 57, 576-579.

DOI: 10.1039/D0CC07540J　Highlighted as an outside front cover picture!

2020

Monoradicals and Diradicals of Dibenzofluoreno[3,2-b]fluorene Isomers: Mechanisms of Electronic Delocalization

H. Hayashi, J. E. Barker, A. C. Valdivia, R. Kishi, S. N. MacMillan, C. J. Gómez-García, H. Miyauchi, Y. Nakamura, M. Nakano, S.-i. Kato, M. M. Haley, J. Casado

J. Am. Chem. Soc. 2020, 142, 20444-20455.

DOI: 10.1021/jacs.0c09588

Open-Shell Singlet Diradicaloid Difluoreno[4,3-b:3’,4’-d]furan and its Radical Cation and Dianion

S. Mori, M. Akita, S. Suzuki, M. S. Asano, M. Murata, T. Akiyama, T. Matsumoto, C. Kitamura, S.-i. Kato

Chem. Commun. 2020, 56, 5881-5884.

DOI: 10.1039/D0CC01638A Highlighted as an inside front cover picture! Highlighted in SYNFACTS

Chemical Transformations of Push–Pull Fluorenones: Push–Pull Dibenzodicyanofulvenes as well as Fluorenone– and Dibenzodicyanofulvene–Tetracyanobutadiene Conjugates

S.-i. Kato, T. Kijima, Y. Shiota, T. Abe, S. Kuwako, H. Miyauchi, N. Yoshikawa, K. Yoshizawa, T. Yoshihara, S. Tobita, Y. Nakamura

Org. Biomol. Chem. 2020, 18, 4198-4209.

DOI: 10.1039/C9OB02706H Highlighted as an outside front cover picture!

Synthesis, Structures, and Properties of Neutral and Radical Cationic S,C,C-Bridged Triphenylamines

S.-i. Kato, T. Matsuoka, S. Suzuki, M. S. Asano, T. Yoshihara, S. Tobita, T. Matsumoto, C. Kitamura

Org. Lett. 2020, 22, 734-738.

DOI: 10.1021/acs.orglett.9b04575

Reductive Methylation of Triphthaloylbenzene: Isolation and Characterization of Hexamethoxy-trinaphthylene and Two Unexpected Trinaphthylene Derivatives

K. Nishida, K. Ono, S.-i. Kato, C. Kitamura

Tetrahedron Lett. 2020, 61, 152422.

DOI: 10.1016/j.tetlet.2020.152422

Effects of Fluorine Substitution in Quinoidal Oligothiophenes for Use as Organic Semiconductors

K. Yamamoto, S.-i. Kato, H. Zajaczkowska, T. Marszalek, P. W. M. Blom, Y. Ie

J. Mater. Chem. C 2020, 8, 3580-3588.

DOI: 10.1039/C9TC06598A

White-light Emission from a Pyrimidine–Carbazole Conjugate with Tunable Phosphorescence–Fluorescence Dual Emission and Multicolor Emission Switching

T. Ishi-i, H. Tanaka, I. S. Park, T. Yasuda, S.-i. Kato, M. Ito, H. Hiyoshi, T. Matsumoto

Chem. Commun. 2020, 56, 4051-4054.

DOI: 10.1039/D0CC00251H　Highlighted as an inside front cover picture!

Visualization of Lipid Droplets in Living Cells and Fatty Livers of Mice Based on the Fluorescence of π-Extended Coumarin Using Fluorescence Lifetime Imaging Microscopy

T. Yoshihara, R. Maruyama, S. Shiozaki, K. Yamamoto, S.-i. Kato, Y. Nakamura, S. Tobita

Anal. Chem. 2020, 92, 4996-5003.

DOI: 10.1021/acs.analchem.9b05184

2019

Mechanochromic Fluorescence Based on a Combination of Acceptor and Bulky Donor Moieties: Tuning Emission Color and Regulating Emission Change Direction

T. Ishi-i, H. Tanaka, R. Youfu, N. Aizawa, T. Yasuda, S.-i. Kato, T. Matsumoto

New J. Chem. 2019, 43, 4998-5010.

DOI: 10.1039/C8NJ06050A　Highlighted as an outside front cover picture!

2018

2,4,5,7,9,10-Hexaethynylpyrenes: Synthesis, Properties, and Self-Assembly

S.-i. Kato, H. Kano, K.-i. Irisawa, N. Yoshikawa, R. Yamamoto, C. Kitamura, D. Nara, T. Yamanobe, H. Uehara, Y. Nakamura

Org. Lett. 2018, 20, 7350-7354.

DOI: 10.1021/acs.orglett.8b03290　Highlighted in ChemistryViews

Trithiazolyl-1,3,5-triazines Bearing Decyloxybenzene Moieties: Synthesis, Photophysical, and Electrochemical Properties, as well as Self-Assembly Behavior

S.-i. Kato, S. Jin, T. Kimura, N. Yoshikawa, D. Nara, K. Imamura, Y. Shiota, K. Yoshizawa, R. Katoono, T. Yamanobe, H. Uehara, Y. Nakamura

Org. Biomol. Chem. 2018, 16, 3584-3595.

DOI: 10.1039/C8OB00471D

10-Mesityl-1,8-diphenylanthracene Dimer: Synthesis, Structure, and Properties

A. Shirai, H. Sano, Y. Nakamura, M. Takashika, H. Otani, M. Hasegawa, S.-i. Kato, M. Iyoda

J. Org. Chem. 2018, 83, 3857-3863.

DOI: 10.1021/acs.joc.8b00200

Synthesis of Isomeric Coumarin-Fluorene Hybrids by Photocyclization and the Photophysical Features

M. Yamaji, H. Okamoto, K. Goto, S.-i. Kato, F. Tani, Y. Nakamura

Tetrahedron Lett. 2018, 59, 1216-1216.

DOI: 10.1016/j.tetlet.2018.02.033

2017

Tetraalkoxyphenanthrene-Fused Hexadecadehydro[20]- and Tetracosadehydro[30]annulenes: Syntheses, Aromaticity/Antiaromaticity, Electronic Properties, and Self-Assembly

N. Takahashi, S.-i. Kato, M. Yamaji, M. Ueno, R. Iwabuchi, Y. Shimizu, M. Nitani, Y. Ie, Y. Aso, T. Yamanobe, H. Uehara, Y. Nakamura

J. Org. Chem. 2017, 82, 8882-8896.

DOI: 10.1021/acs.joc.7b01165　Highlighted in SYNFACTS

Tetraalkoxyphenanthrene-Fused Thiadiazoloquinoxalines: Synthesis, Electronic, Optical, and Electrochemical Properties, and Self-Assembly

S.-i. Kato, K. Watanabe, M. Tamura, M. Ueno, M. Nitani, Y. Ie, Y. Aso, T. Yamanobe, H. Uehara, Y. Nakamura

J. Org. Chem. 2017, 82, 3132-3143.

DOI: 10.1021/acs.joc.7b00084

Blue Fluorescence from BF2 Complexes of N,O -Benzamide Ligands: Synthesis, Structure, and Photophysical Properties

M. Yamaji, S.-i. Kato, K. Tomonari, M. Mamiya, K. Goto, H. Okamoto, Y. Nakamura, F. Tani

Inorg. Chem. 2017, 56, 12514-12519.

DOI: 10.1021/acs.inorgchem.7b02013

2016

Benzo- and Naphthopentalenes: Syntheses, Structures, and Properties

S.-i. Kato, S. Kuwako, N. Takahashi, T. Kijima, Y. Nakamura

J. Org. Chem. 2016, 81, 7700-7710.

DOI: 10.1021/acs.joc.6b01409

Push‒Pull Fluorenones and Benzazulenequinones: Regioselective [4+2] and [2+2] Cycloadditions of Benzopentalenequinone Derivative and Alkynes Bearing an Aniline Moiety

S.-i. Kato, T. Kijima, Y. Shiota, T. Yoshihara, S. Tobita, K. Yoshizawa, Y. Nakamura

Tetrahedron Lett. 2016, 57, 4604-4607.

DOI: 10.1016/j.tetlet.2016.09.002

Synthesis, Self-Association, and Anion Recognition of Conjugated Macrocycles Composed of Carbazole and Triazolium Moieties

S. Jin, S.-i. Kato, Y. Nakamura

Chem. Lett. 2016, 45, 869-871.

DOI: 10.1246/cl.160400

Synthesis and Electronic, Optical, and Electrochemical Properties of a Series of Tetracyanobutadiene-Substituted Carbazoles

S.-i. Kato, H. Noguchi, S. Jin, Y. Nakamura

Asian J. Org. Chem. 2016, 5, 246-256.

DOI: 10.1002/ajoc.201500431

Photochemical Synthesis and Photophysical Features of Ethynylphenanthrenes Studied by Emission and Transient Absorption Measurements

Y. Hakoda, M. Aoyagi, K. Irisawa, S.-i. Kato, Y. Nakamura, M. Yamaji

Photochem. Photobiol. Sci. 2016, 15, 1586-1593.

DOI: 10.1039/C6PP00291A

2015

Series of Carbazole‒Pyrimidine Conjugates: Synthesis and Electronic, Photophysical, and Electrochemical Properties

S.-i. Kato, Y. Yamada, H. Hiyoshi, K. Umezu, Y. Nakamura

J. Org. Chem. 2015, 80, 9076-9090.

DOI: 10.1021/acs.joc.5b01409

A Series of π-Extended Thiadiazoles Fused with Electron-Donating Heteroaromatic Moieties: Syntheses, Properties, and Polymorphic Crystals

S.-i. Kato, T. Furuya, M. Nitani, N. Hasebe, Y. Ie, Y. Aso, T. Yoshihara, S. Tobita, Y. Nakamura

Chem. Eur. J. 2015, 21, 3115-3128.

DOI: 10.1002/chem.201405478

2014

Systematic Structure‒Property Investigations on a Series of Alternating Carbazole‒Thiophene Oligomers

S.-i. Kato, S. Shimizu, A. Kobayashi, T. Yoshihara, S. Tobita, Y. Nakamura

J. Org. Chem. 2014, 79, 618-629.

DOI: 10.1021/jo402416f

From Homoconjugated Push‒Pull Chromophores to Donor‒Acceptor-Substituted Spiro Systems by Thermal Rearrangement

C. Dengiz, O. Dumele, S.-i. Kato, M. Zalibera, P. Cias, W. B. Schweizer, C. Boudon, J.-P. Gisselbrecht, G. Gescheidt, F. Diederich

Chem. Eur. J. 2014, 20, 1279-1286.

DOI: 10.1002/chem.201303533

2013

Hexadecadehydrodibenzo[20]-, Tetracosadehydrotribenzo[30]-, and Dotriacontadehydrotetrabenzo[40]annulenes: Syntheses, Characterizations, Electronic Properties, and Self-Associations

S.-i. Kato, N. Takahashi, Y. Nakamura

J. Org. Chem. 2013, 78, 7658-7663.

DOI: 10.1021/jo401200m

Tetraalkoxyphenanthrene-Fused Dehydroannulenes: Synthesis, Self-Assembly, and Electronic, Optical, and Electrochemical Properties

S.-i. Kato, N. Takahashi, H. Tanaka, A. Kobayashi, T. Yoshihara, S. Tobita, T. Yamanobe, H. Uehara, Y. Nakamura

Chem. Eur. J. 2013, 19, 12138-12151.

DOI: 10.1002/chem.201301262

Synthesis and Properties of Disiloxane-bridged Cyclophanes Bearing Heteroaromatics

S.-i. Kato, N. Yamazaki, T. Tajima, Y. Nakamura

Chem. Lett. 2013, 42, 401-403.

DOI: org/10.1246/cl.121271

Photochemical Behaviors of a Tethered 1,3-Diketone Derivative Studied by Transient Absorption and Time-resolved EPR Measurements

A. Kobayashi, M. Yamaji, S. Nakajima, K. Akiyama, S. Tero-Kubota, S.-i. Kato, Y. Nakamura

Chem. Phys. Lett. 2013, 555, 101-105.

DOI: 10.1016/j.cplett.2012.10.067

2012

Bicarbazoles: Systematic Structure-Property Investigations on a Series of Conjugated Carbazole Dimers

S.-i. Kato, H. Noguchi, A. Kobayashi, T. Yoshihara, S. Tobita, Y. Nakamura

J. Org. Chem. 2012, 77, 9120-9133.

DOI: 10.1021/jo3016538

π-Extended Thiadiazoles Fused with Thienopyrrole or Indole Moieties: Synthesis, Structures, and Properties

S.-i. Kato, T. Furuya, A. Kobayashi, M. Nitani, Y. Ie, Y. Aso, T. Yoshihara, S. Tobita, Y. Nakamura

J. Org. Chem. 2012, 77, 7595-7606.

DOI: 10.1021/jo301458m　Highlighted in SYNFACTS

Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazol

S.-i. Kato, S. Shimizu, H. Taguchi, A. Kobayashi, S. Tobita, Y. Nakamura

J. Org. Chem. 2012, 77, 3222-3232.

DOI: 10.1021/jo202625p

~2011

Synthesis of [60]Fullerene-Containing [2]Rotaxanes Using Axle Molecules Bearing Donor Moiety

Y. Kasai, C. Sakamoto, N. Muroya, S.-i. Kato, Y. Nakamura

Tetrahedron Lett. 2011, 52, 623-625.

DOI: 10.1016/j.tetlet.2010.11.155

Homoconjugated Push‒Pull and Spiro Systems: Intramolecular Charge-Transfer Interactions and Third-Order Nonlinearlities

S.-i. Kato, M. T. R. Beels, P. La Porta, W. B. Schweizer, C. Boudon, J.-P. Gisselbrecht, I. Biaggio, F. Diederich

Angew. Chem. Int. Ed. 2010, 49, 6207-6211.

DOI: 10.1002/anie.201002236

Molecular Recognition Properties of Polymethoxybenzenes by Host Molecules Comprised of Two Pyromellitic Diimides and Two Dialkoxynaphthalenes

T. Nakagaki, S.-i. Kato, A. Harano, T. Shinmyozu

Tetrahedron 2010, 66, 976-985.

DOI: 10.1016/j.tet.2009.11.087

Origin of Intense Intramolecular Charge-Transfer Interactions in Non-Planar Push‒Pull Chromophores

S.-i. Kato, M. Kivala, W. B. Schweizer, C. Boudon, J.-P. Gisselbrecht, F. Diederich

Chem. Eur. J. 2009, 15, 8687-8691.

DOI: 10.1002/chem.200901630

Novel Pyromellitic Diimide-Based Macrocycle with a Linear π-Electronic System and Bis(phenylethynyl)pyromellitic Diimide: Syntheses, Structures, Photophysical Properties, and Redox Characteristics

S.-i. Kato, Y. Nonaka, T. Shimasaki, K. Goto, T. Shinmyozu

J. Org. Chem. 2008, 73, 4063-4075.

DOI: 10.1021/jo800283r

One-pot Synthesis of Macrocyclic Compounds Possessing Two Cyclobutane Rings by Sequential Inter- and Intramolecular [2 + 2] Photocycloaddition Reactions

H. Miyauchi, C. Ikematsu, T. Shimasaki, S.-i. Kato, T. Shinmyozu, T. Shimo, K. Somekawa

Tetrahedron 2008, 64, 4108-4116.

DOI: 10.1016/j.tet.2008.02.005

The First X-Ray Crystallographic Evidence of a Cyclic Aniline Trimer via Self-Complementary N–H··· π Interactions: The Aniline Inclusion both inside and outside the Macrocyclic Cavity

S.-i. Kato, T. Nakagaki, T. Shimasaki, T. Shinmyozu

CrystEngComm 2008, 10, 483-486.

DOI: 10.1039/B718306B

Synthesis, Structural, Spectral, and Photoswitchable Properties of cis- and trans- 2,2,13,13-Tetramethyl- 1,1'-indanylindanes

T. Shimasaki, S.-i. Kato, T. Shinmyozu

J. Org. Chem. 2007, 72, 6251-6254.

DOI: 10.1021/jo0701233

Singlet Oxygen Generation by Two-Photon Excitation of Porphyrin Derivatives Having Two-Photon- Absorbing Benzothiadiazole Chromophores

T. Ishi-i, Y. Taguri, S.-i. Kato, M. Shigeiwa, H. Gorohmaru, S. Maeda, S. Mataka

J. Mater. Chem. 2007, 17, 3341-3346.

DOI: 10.1039/B704499B

Synthesis and Structural and Photoswitchable Properties of Novel Chiral Host Molecules: Axis Chiral 2,2'-Dihydroxy-1,1'-binaphtyl Appended stiff-Stilbene

T. Shimasaki, S.-i. Kato, K. Ideta, K. Goto, T. Shinmyozu

J. Org. Chem. 2007, 72, 1073-1087.

DOI: 10.1021/jo061127v

Supramolecular Assemblies and Redox Modulation of Pyromellitic Diimide-Based Cyclophane via Noncovalent Interactions with Naphthol

S.-i. Kato, T. Matsumoto, K. Ideta, T. Shimasaki, K. Goto, T. Shinmyozu

J. Org. Chem. 2006, 71, 4723-4733.

DOI: 10.1021/jo0600196

Novel 2,1,3-Benzothiadiazole-Based Red-Fluorescent Dyes with Enhanced Two-Photon Absorption Cross-Sections

S.-i. Kato, T. Matsumoto, M. Shigeiwa, H. Gorohmaru, S. Maeda, T. Ishi-i, S. Mataka

Chem. Eur. J. 2006, 12, 2303-2317.

DOI: 10.1002/chem.200500921

Strongly Red-Fluorescent Novel Donor-π-Bridge-Acceptor-π-Bridge-Donor Type 2,1,3-Benzothiadiazoles with Enhanced Two-Photon Absorption Cross-Sections