Hiroto Lab

Graduate School of Human and Environmental Studies, Kyoto University
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List of Publications

2024

(1) Donor-acceptor-donor Dyads with Electron-rich π-Extended Azahelicenes to Panchromatic Absorbing Dyes
S. Hiroto, M. Chujo
Chem. Asian. J., Accepted. (2024).

2023

(1) Synthesis of π-extended aza[5]helicenes bearing Au(I)-acetylides at the outside or inside of the helix
S. Hiroto, M. Ura
Tetrahedron Lett., 123, 154533. (2023).

2022

(1) A Strategy for Polar Crystals with Dipolar Heterohelicenes
S. Hiroto, M. Wakita, M. Chujo
Chem. Asian. J, 17, e202200808 (2022).

2021

(1) Heteroatoms in bowl-shaped polycyclic aromatic hydrocarbons: Synthesis and structures
S. Hiroto
Chem. Lett., 50, 1146-1155 (2021).

2020

(2) “Helical pitch dependent optical properties of π-extended aza[5]helicene radical cations”
S. Hiroto,
Bull. Chem. Soc. Jpn. , 93, 1334-1338 (2020) (doi: 10.1246/bcsj.20200181).
(1) Development of synthetic protocols for porphyrins and their analogs based on distorted structures (Award Account)
S. Hiroto
J. Porphyrins Phthalocyanines, 24, 1258 (2020).

2019

(6) “Amplified Heavy-Atom Free Phosphorescence from Meta-Dimethoxy Difluoroboron β-Diketonate Charge-Transfer Materials”
C. DeRosa, S. Hiroto, C. L. Fraser,
J. Phys. Chem. C. , 123, 20488 (2019).
(5) “Regioselective desilylation of a π-extended aza[5]helicene”
A. Ushiyama, H. Shinokubo, *S. Hiroto,
Chem. Lett., 48, 1069 (2019).
(4) “Ni(II) 10-Phosphacorrole: A Porphyrin Analogue Containing Phosphorus at the Meso Position”
H. Omori, S. Hiroto, Y. Takeda, H. Fliegl, S. Minakata, *H. Shinokubo
J. Am. Chem. Soc., 141, 4800-4805 (2019).
(3) “Synthesis of dihydropyrazine-fused porphyrin dimers”
A. Takiguchi, M. Wakita, *S. Hiroto, *H. Shinokubo
Chem. Lett., 48, 371-373. (2019).
Selected as Editor's Choice
(2) π‐Conjugated Compounds for Molecular Materials (Editorial)
S. Hiroto, J. Wu
Chem. Asian. J., 14, 1600 (2019).
(1) Synthesis of π‐functional molecules through oxidation of aromatic amines
S. Hiroto
Chem. Asian. J., 14, 2514 (2019)

2018

(6) “X-Shaped Cyclobutane-Linked Tetraporphyrins through a Thermal [2+2] Cycloaddition of Etheno-Fused Diporphyrins”
T. Nagai, A. Takiguchi, M. Ueda, K. Oda, S. Hiroto, *H. Shinokubo
J. Am. Chem. Soc., 140, 8392. (2018).
(5) “Azabuckybowl-Based Molecular Tweezers as C60 and C70 Receptors”
M. Takeda, *S. Hiroto, H. Yokoi, S. Lee, *D. Kim, *H. Shinokubo
J. Am. Chem. Soc., 140, 6336-6342. (2018).
Highlighted in Supplementary cover
(4) “Reversible σ-Bond Formation in Bowl-Shaped π-Radical Cations: The Effects of Curved and Planar Structures”
H. Yokoi, *S. Hiroto, *H. Shinokubo
J. Am. Chem. Soc., 140, 4649–4655. (2018).
(3) “Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60”
H. Yokoi, *S. Hiroto, D. Sakamaki, S. Seki, *H. Shinokubo
Chem. Sci., 9, 819-824. (2018).
Highlighted in Inside Front cover
(2) Innovative Synthesis and Functions of Curved-π Conjugated Molecules
S. Hiroto
Bull. Chem. Soc. Jpn., 91, 829 (2018).
(1) Synthesis of Heteroatom-Containing Curved π-Conjugated Molecules
S. Hiroto, H. Shinokubo
J. Synth. Org. Chem. Jpn., 76, 37-44. (2018).

2017

(7) “Acid-Mediated Migration of Bromide in an Antiaromatic Porphyrinoid: Preparation of Two Regioisomeric Ni(II) Bromonorcorroles”
H. Kawashima, S. Hiroto, *H. Shinokubo
J. Org. Chem., 72, 10425-10432 (2017).
(6) “Shaping Antiaromatic π-System by Metallation: Synthesis of a Bowl-Shaped Antiaromatic Pd-Norcorrole”
T. Yonezawa, S. A. Shafie, S. Hiroto, *H. Shinokubo
Angew. Chem. Int. Ed., 56, 11822-11825 (2017).
(5) “π-Extended Dihydrophenazines with Three-State NIR Electrochromism Involving Large Conformational Changes”
J. Nagasaki, *S. Hiroto, *H. Shinokubo
Chem. Asian. J., 12, 2311-2317 (2017).
Highlighted in Front cover
(4) “NIR Mechanochromic Behaviours of Tetracyanoethylene-Bridged Hexa-peri-Hexabenzocoronene Dimer and Trimer through Dissociation of C-C Bonds”
K. Oda, *S. Hiroto, *H. Shinokubo
J. Mater. Chem. C, 5, 5310-5315 (2017).
Highlighted in Front cover
Selected as Hot Paper
(3) “10-Silacorroles Exhibiting NIR Absorption and Emission”
H. Omori, *S. Hiroto, *H. Shinokubo
Chem. Eur. J., 23, 7866 (2017).
Highlighted in frontispiece
Selected as Hot Paper
(2) “Synthesis of bright red-emissive dicyanoetheno-bridged hexa-peri-hexabenzocoronene dimers”
K. Oda, *S. Hiroto, *H. Shinokubo
Org. Biomol. Chem., 15, 1426-1434 (2017).
(1) “Synthesis of a figure-eight azahelicene dimer with high emission and CPL properties”
A. Ushiyama, *S. Hiroto, J. Yuasa, T. Kawai, *H. Shinokubo
Org. Chem. Front., 4 664 (2017).

2016

(5) “Synthesis of Free-Base 10-Azacorroles”
H. Omori, *S. Hiroto, *H. Shinokubo
Org. Lett., 18, 2978-2981 (2016).
(4) “Control of Conformation and Chirality of Nonplanar π-Conjugated Diporphyrins Using Substituents and Axial Ligands”
S. Ito, *S. Hiroto, N. Ousaka, E. Yashima, *H. Shinokubo
Chem. Asian. J., 11, 936-942 (2016).
Highlighted in inside cover
(3) “Synthesis of Ni(II) and Al(III) 10-azacorroles through coordination-induced cyclisation involving 1,2-migration”
H. Omori, *S. Hiroto, *H. Shinokubo
Chem. Commun., 52, 3540-3543 (2016).
(2) “Fully-Substituted 1,3-Butadienes as π-Conjugated Linkers between Pyrenes”
K. Oda, *S. Hiroto, D. Sakamaki, S. Seki, *H. Shinokubo
Chem. Lett., 45, 403-405 (2016).
(1) Synthesis and Functionalization of Porphyrins through Organometallic Methodologies
S. Hiroto, Y. Miyake, H. Shinokubo
Chem. Rev., 117, 2910-3043. (2016).

2015

(6) “Indolylindolinone: Easily Accessible, Tunable, and Wide-Range Absorbing Dyes”
A. Shigeno, T. Matsuno, *S. Hiroto, *H. Shinokubo
Chem. Lett., 44, 1703-1705. (2015).
(5) “Nitrogen-embedded buckybowl and its assembly with C60”
H. Yokoi, Y. Hiraoka, *S. Hiroto, D. Sakamaki, S. Seki, *H. Shinokubo
Nat. Commun., 6, 8215. (2015).
Highlighted in Natureasia
(4) “Regioselective Nucleophilic Functionalization of Antiaromatic Ni(II) Norcorrole”
R. Nozawa, K. Yamamoto, J.-Y. Shin, S. Hiroto, *H. Shinokubo
Angew. Chem. Int. Ed., 54, 8454-8457. (2015).
(3) “Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene”
T. Matsuno, Y. Koyama, *S. Hiroto, J. Kumar, T. Kawai, *H. Shinokubo
Chem. Commun., 51, 4607-4610 (2015).
(2) “Macrocyclic dipyrrin dimer bridged by ethylene and dioxyphenylene linkers”
J.-Y. Shin, S. Hiroto, *H. Shinokubo
J. Porphyrins Phthalocyanines, 19, 135-139 (2015).
(1) “Synthesis of Highly Twisted and Fully π-Conjugated Porphyrinic Oligomers”
S. Ito, *S. Hiroto, S. Lee, M. Son, I. Hisaki, T. Yoshida, *D. Kim, *N. Kobayashi, and *H. Shinokubo
J. Am. Chem. Soc., 137, 137, 142-145 (2015).
Highlighted in Japanese Newspaper (Nikkei Sangyo Shinbun)
Press Release from Nagoya University
Open Access from ACS
Highlighted in Synfacts

2014

(8) “Synthesis, Reactivity, and Property of 5,15-Dithiaporphyrin Copper(II) Complex”
N. Wachi, T. Kondo, S. Ito, S. Hiroto, J.-Y. Shin, and *H. Shinokubo
J. Porphyrins Phthalocyanines, 18, 675-678 (2014).
(7) “Synthesis of curved hexa-peri-hexabenzocoronenes”
R. Yamaguchi, *S. Hiroto, *H. Shinokubo
Chem. Lett., 43, 1637-1639 (2014).
(6) “Synthesis of Regioselective Double Cyclization of 5,15-Bis(trimethylsilylethynyl)porphyrin to Provide Di(oxoethano)porphyrin”
K. Oda, *S. Hiroto, *H. Shinokubo
Chem. Lett., 43, 1444-1446 (2014).
(5) “Synthesis of Diazo-Bridged BODIPY Dimer and Tetramer by Oxidative Coupling of beta-Amino-substituted BODIPYs”
H. Yokoi, *S. Hiroto, *H. Shinokubo
Org. Lett., 16, 3004-3007 (2014).
(4) “Facile Synthesis of Nitrogen-Containing Polycyclic Aromatic Hydrocarbons from Perylene Bisimides”
S. Ito, *S. Hiroto, *H. Shinokubo
Chem. Lett., 43, 1309-1311 (2014).
(3) “Silylethynyl Substituents as Porphyrin Protecting Groups for Solubilization and Selectivity Control”
K. Oda, M. Akita, *S. Hiroto, *H. Shinokubo
Org. Lett., 16, 1818-1821 (2014).
(2) “Oxidation of 2-amino-substituted BODIPYs providing pyrazine-fused BODIPY trimers”
H. Yokoi, N. Wachi, *S. Hiroto, *H. Shinokubo
Highlighted as back cover
Chem. Commun., 50, 2715-2717 (2014).
(1) “Near-IR Absorbing Silaporphyrinoids Prepared by Regioselective Insertion of Silylenes into Antiaromatic Norcorrole”
T. Fukuoka, K. Uchida, Y. M. Sung, J.-Y. Shin, S. Ishida, J. M. Lim, S. Hiroto, K. Furukawa, *D. Kim, *T. Iwamoto, and *H. Shinokubo
Angew. Chem. Int. Ed., 53, 1506-1509 (2014).
Highlighted in frontispiece

2013

(6) “Assembled Structures of Dipyrrins and Their Oligomers Bridged by Dioxy-Boron Moieties”
*H. Maeda, Y. Nishimura, S. Hiroto, *H. Shinokubo
Dalton. Trans., 42, 15885-15888 (2013).
(5) “Synthesis of Pyridine-Fused Perylene Imides with an Amidine Moiety for Hydrogen Bonding”
S. Ito, S. Hiroto, *H. Shinokubo
Org. Lett., 15, 3110-3113 (2013).
(4) “Synthesis of Highly Distorted pi-Extended [2.2]Metacyclophanes by Intermolecular Double Oxidative Coupling”
Y. Koyama, *S. Hiroto, *H. Shinokubo
Angew. Chem. Int. Ed., 52, 5740-5743 (2013).
(3) “Carbolithiation of meso-Aryl-Substituted 5,15-Diazaporphyrin Selectively Provides 3-Alkylated Diazachlorins”
A. Yamaji, S. Hiroto, J.-Y. Shin, *H. Shinokubo
Chem. Commun., 49, 5064-5066 (2013).
(2) “Porphyrin Analogues That Consist of Indole, Benzofuran, and Benzothiophene Subunits”
S. Nakamura, T. Kondo, *S. Hiroto, *H. Shinokubo
Asian. J. Org. Chem., 2, 312-319 (2013).
Highlighted in frontispiece
(1) “Functionalization of Hexa-peri-hexabenzocoronenes: Investigation of Substituent Effects on a Superbenzene”
R. Yamaguchi, S. Ito, B. S. Lee, S. Hiroto, *D. Kim, *H. Shinokubo
Chem. Asian. J., 8, 178-190 (2013).

2012

(5) “Intermolecular Oxidative Annulation of 2-Aminoanthracenes to Diazaacenes and Aza[7]helicenes”
K. Goto, R. Yamaguchi, *S. Hiroto, H. Ueno, T. Kawai, *H. Shinokubo
Angew. Chem. Int. Ed., 51, 10333-10336(2012).
Highlighted in inside back cover
(4) “Synthesis of Oxygen-Substituted Hexa-peri-hexabenzocoronenes through Ir-Catalyzed Direct Borylation”
R. Yamaguchi, S. Hiroto, *H. Shinokubo
Org. Lett., 14, 2472-2475(2012).
(3) “Energy and Electron Transfer from Fluorescent Mesostructured Organosilica Framework to Guest Dyes”
N. Mizoshita, K. Yamanaka, S. Hiroto, H. Shinokubo, T. Tani, and *S. Inagaki
Langmuir, 28, 3987-3994 (2012).
(2) “Oxidative Annulation of β-Aminoporphyrins to Provide Pyrazine-Fused Diporphyrins”
M. Akita, S. Hiroto, *H. Shinokubo
Angew. Chem. Int. Ed., 51, 2894-2897.(2012).
(1) “Synthesis and oxidation of cyclic tetraindole”
S. Nakamura, *S. Hiroto, *H. Shinokubo
Chem. Sci., 3, 524-527 (2012).
Highlighted in Synfacts

2011

(3) “Functionalization of a Simple Dithienylethane via Palladium-Catalyzed Regioselective Direct Arylation"”
H. Kamiya, S. Yanagisawa, S. Hiroto, *K. Itami, *H. Shinokubo
Org. Lett., 13, 6394-6397 (2011).
(2) “Iridium-Catalyzed Direct Tetraborylation of Perylene Bisimides”
T. Teraoka, S. Hiroto, *H. Shinokubo
Org. Lett., 13, 2532-2535 (2011).
Highlighted in Synfacts
(1) “Synthetic protocol for diarylethenes through Suzuki-Miyaura coupling”
S. Hiroto, K. Suzuki, H. Kamiya, *H. Shinokubo
Chem. Commun., 47, 7149-7151 (2011).

before 2010

(15) “Excess Polarizability Reveals Exciton Localization/Delocalization Controlled by Linking Positions on Porphyrin Rings in Butadiyne-Bridged Porphyrin Dimers”
C. She, S. Easwaramoorthi, P. Kim, S. Hiroto, I. Hisaki, *H. Shinokubo, *A. Osuka, *D. Kim, J. *T. Hupp
J. Phys. Chem. A, 114, 3384-3390 (2010).
(14) “Unusual Interchromophoric Interactions in β,β’ Directly and Doubly Linked Corrole Dimers; Prohibited Electronic Communication and Abnormal Singlet Ground States”
S. Cho, J. Lim, S. Hiroto, P. Kim, *H. Shinokubo, *A. Osuka, *D. Kim
J. Am. Chem. Soc., 131, 6412-6420 (2009).
(13) “Conformational Changes of meso-Aryl Substituted Expanded Porphyrins upon Protonation: Effects on Photophysical Properties and Aromaticity”
J.-Y. Shin, J. M. Lim, Z. S. Yoon, K. S. Kim, M.-C. Yoon, S. Hiroto, *H. Shinokubo, S. Shimizu, *A. Osuka, *D. Kim
J. Phys. Chem. B, 113, 5794-5802 (2009).
(12) “Zwitterionic Corrole: Regioselective Nucleophilic Pyridination of a Doubly Linked Biscorrole”
S. Hiroto, N. Aratani, N. Shibata, Y. Higuchi, T. Sasamori, N. Tokitoh, *H. Shinokubo, *A. Osuka
Angew. Chem. Int. Ed., 48, 2388-2390 (2009).
(11) “First self-assembly study of large pi-conjugated corrole dimers on solid substrates”
X. Miao, A. Gao, Z. Li, S. Hiroto, *H. Shinokubo, *A. Osuka, W*. Deng
Appl. Surf. Sci., 255, 5885-5890 (2009).
(10) “Adsorption characteristic of self-assembled corrole dimers on HOPG”
X. Miao, A. Gao, S. Hiroto, *H. Shinokubo, *A. Osuka, J. Xin, W. Deng
Surf. Interface. Anal., 41, 225-230 (2009).
(9) “Porphyrin Derivatives with Carbon-Metal bond”
S. Hiroto, S. Yamaguchi, H. Shinokubo, A. Osuka
J. Synth. Org. Chem. Jpn., 67, 688. (2009).
(8) “Synthesis of Directly and Doubly Linked Dioxoisobacteriochlorin Dimers“
S. Hiroto, I. Hisaki, *H. Shinokubo, *A. Osuka
J. Am. Chem. Soc., 130, 16172-16173 (2008).
(7) “2,5-Thienylene-Bridged Triangular and Linear Porphyrin Trimers”
J. Song, S. Y. Jang, S. Yamaguchi, J. Sankar, S. Hiroto, N. Aratani, J.-Y. Shin, S. Easwaramoorthi, K. S. Kim, *D. Kim, *H. Shinokubo, *A. Osuka
Angew. Chem. Int. Ed., 47, 6004-6007 (2008).
(6) “Synthesis of Doubly β-to-β 1,3-Butadiyne-Bridged Diporphyrins: Enforced Planar Structures and Large Two-photon Absorption Cross Sections.”
I. Hisaki, S. Hiroto, K. S. Kim, S. B. Noh, *D. Kim, *H. Shinokubo, *A. Osuka
Angew. Chem. Int. Ed., 46, 5125-5128 (2007).
(5) “Regioselective Borylation of Porphyrins via C-H Bond Activation under Iridium Catalysis That Affords Useful Building Blocks for Porphyrin Assemblies”
H. Hata, S. Yamaguchi, G. Mori, S. Nakazono, T. Katoh, K. Takatsu, S. Hiroto, *H. Shinokubo, *A. Osuka
Chem. Asian J., 2, 849-859 (2007).
(4) “Synthesis and Biradicaloid Character of a Doubly Linked Biscorrole”
S. Hiroto, K. Furukawa, *H. Shinokubo, *A. Osuka
J. Am. Chem. Soc., 128, 12380-12381 (2006).
(3) “Porphyrin Synthesis in Water Provides New Expanded porphyrins with Direct Bipyrrole Linkages: Isolation and Characterization of Two Heptaphyrins”
S. Hiroto, *H. Shinokubo, *A. Osuka
J. Am. Chem. Soc., 128, 6568-6569 (2006).
(2) “Synthesis of Corrole Derivatives through Regioselective Ir-Catalyzed Direct Borylation”
S. Hiroto, I. Hisaki, *H. Shinokubo, *A. Osuka
Angew. Chem. Int. Ed., 44, 6763-6766 (2005).
(1) “meso-Alkyl meso-meso Linked Diporphyrin and meso-meso, β-β, β-β Triply Linked Diporphyrin”
S. Hiroto, *A. Osuka
J. Org. Chem., 70, 4054-4058 (2005).

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Reviews and Accounts

(3) 大きく歪んだπ共役分子の新規合成法
廣戸 聡
化学と工業, 9月号, 830-831. (2015).
(2) π共役平面をひねって一回転させる
廣戸 聡、忍久保 洋
高分子, 64巻, 11月号, 713-714. (2015).
(1) フェノールの脱芳香環化を伴うエナンチオ選択的分子間反応
S. Hiroto
J. Synth. Org. Chem. Jpn., 72, 181. (2013).

Books

(2) Syntheses and Properties of Antiaromatic Porphyrinoids
S. Hiroto, H. Shinokubo
Handbook of Porphyrin Science vol. 37, K. M. Kadish, K. M. Smith, R. Guilard, Eds., World Scientific, Singapore, (2016).
(1) ジアリールエテンの新規合成法の開発
廣戸 聡、忍久保 洋
フォトクロミズムの攻究とメカニカル機能の創出, 入江 正浩 監修, シーエムシー出版,, 159-169. (2011).

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