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成果及论文

Liuhui Wu, Pei Li, Ling Xu, Yutao Rao, Bangshao Yin, Mingbo Zhou, Jianxin Song,* and Atsuhiro Osuka, m-Pyripentaphyrins(1.0.0.0.0): BIII Complexes and β-β Directly Linked Dimers, Chem. Asian J. 2024, e202400649.

Yutao Rao,* Jiyeon Lee, Jinchao Chen, Ling Xu, Mingbo Zhou, Bangshao Yin, Jiwon Kim,* Atsuhiro Osuka,* and Jianxin Song*, 5,18-Dimesitylorangarin: a Stable Antiaromatic [20]Pentaphyrin(1.0.1.0.0) Displaying Remarkable Oxidative Self-Coupling Reactions, Angew. Chem. Int. Ed. 2024, 63e202409655.



Yang Liu, Ling Xu, Xiaorong Jin, Bangshao Yin, Yutao Rao, Mingbo Zhou, Jianxin Song* and Atsuhiro Osuka, The Unprecedented Strong Paratropic Ring Current of a bis-PdII Complex of 5,10,23-Trimesityl [28]Heptaphyrin(1.1.0.0.1.0.0), Chem. Sci202415, 11402.

 


Yang Liu, Takayuki Tanaka, Daiki Shimizu, Yutao Rao, Ling Xu, Bangshao Yin, Mingbo Zhou, Jianxin Song,* and Atsuhiro Osuka, Fused Aromatic and Antiaromatic Smaragdyrin Dimers, Angew. Chem. Int. Ed. 2024, 63, e202408478.


Lina Wang, Zian Liao, Peng Lin, Yingying Jia, Le Liu, Ling Xu, Mingbo Zhou, Bangshao Yin, Yutao Rao, Akito Nakai, Takayuki Tanaka, Daiki Shimizu, Atsuhiro Osuka and Jianxin Song*, Synthesis of NiII porphyrinNiII 5,15- diazaporphyrin hybrid tapes, Chem. Sci., 2024, 15, 10207.


J. Chen, L. Liu, Y. Rao*, L. Xu, M. Zhou, B. Yin, S. Shimizu, D. Shimizu, A. Osuka*, J. Song*,[22]Pentaphyrins(2.0.1.1.0) Displaying N-Fusion, Pyrrole-Rearrangement, and Dimerization Reactions Upon Oxidation and Metalation,Angew. Chem. Int. Ed. 2024, 63, e202407340.


J. Chen, H. Nie, Y. Rao, L. Xu, M. Zhou, B. Yin, J. Song*, A. Osuka,Carbazole Based Smaragdyrins: Synthesis, Aromaticity Switching, and Formation of a Spiro‐Dimer,Chem Asian J. 2024, 19, e202400029.


Z. Luo, B. Xiao, L. Xu, M. Zhou, B. Yin, Y. Rao, J. Song*, A. Osuka,BIII–Subporphyrins Bearing Distorted Metal-Coordinating Straps: CuII-Assisted meso-Fabrications,Org. Lett. 2024, 26, 1166.


F. Deng, X. Ge, Z. Deng, L. Xu, Y. Rao, B. Yin, M. Zhou, J. Song*, A. Osuka,Copper(II) Carbaporphyrins: Oxygenation Reactivities Dependent upon Coordinating Structures,Inorg. Chem. 2024, 63, 13, 5769–5772.


K. Wang, S. Ito, S. Ren, D. Shimizu, N. Fukui, R. Kishi, Q. Liu, A. Osuka, J. Song*, H. Shinokubo*,A Triply Linked Porphyrin-Norcorrole Hybrid with Singlet Diradical Character,Angew. Chem. Int. Ed. 2024, 63, e202401233.


L. Zi, L. Liu, M. Zhou*, L. Liu, B. xiao, L. Xu, Y. Rao, B. Yin, J. Song*, A. Osuka, Synthesis of Pyrrole-Sharing Fused Porphyrinoid Hybrids by Post-fabrication of Ni(II) Porphyrins, Angew. Chem. Int. Ed2023, 62, e202319005. 


C.Wang, L. Xu, Y. Rao, B. Yin, M. Zhou, J. Song*, A. Osuka, Di(p-dibenzi)[40]decaphyrin(1.0.0.0.0.1.0.0.0.0) PdII Complex: A Weakly Hückel 38π-Aromatic Macrocycle, Chem. Asian J. 2023, 18, e202300923.


B. Wen, C. Li, B. Kang, T. Zheng, Y. Wang, Y. Jiang,  L. Xu,  J. Oh,  A. Osuka,  D. Kim, J. Song*, Cyclic Azobenzene-BODIPY Hybrids, Chem. Eur. J. 2023, e202303193. 

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Y. Liu, L. Xu, Y. Rao, J. Kim, B. Yin, M. Zhou, J. Oh, D. Kim, J. Song*, A. Osuka, Stable Antiaromatic [24]Hexaphyrin(1.1.0.0.1.0) and Its Metal Complexes, Org. Lett. 2023, 25, 8121.


P. Liu, K. Wang, L. Xu, Y. Rao, M. Zhou, A. Osuka, J. Song*, Synthesis of Naphthalene- and Phenanthrene-Fused Smaragdyrins and Their BF2 Complexes,Chem. Asian J. 2023, 18, e202300740.


Q. Pan, L. Liu, Y. Pan, M. Zhou*, L. Xu, Y. Rao, B. Yin, J. Song*, A. Osuka, N-Heterocycle-Fused Ni(II) Porphyrin Dimers Upon Heating of meso-Amino Ni(II) Porphyrins in Nitrobenzene, Org. Chem. Front. 2023, DOI: 10.1039/D3QO01265D.

Graphical abstract: N-Heterocycle-fused Ni(ii) porphyrin dimers upon heating of meso-amino Ni(ii) porphyrins in nitrobenzene


F. Luo, L. Liu, H. Wu, L. Xu, Y. Rao, M. Zhou, A. Osuka, J. Song*, Doubly N-confused and Ring-Contracted [24]Hexaphyrin Pd-Complexes as Stable Antiaromatic N-Confused Expanded Porphyrins, Nat. Commun. 2023, 14, 5028.


F. zhang, Y. Rao, M. Zhou, L. Xu, A. Osuka, J. Song*, Gated Photochromism of Dithienylethene-embeded Expanded Calixphyrins, Chem. Eur. J. 2003, e202302340.


K. Wang Y. Rao L. Xu M. Zhou R. Kurosaki N. Aratani A. Osuka J. Song*,  Post-Installation of Fused Benzoheptagons at the Periphery of NiII Porphyrins: Helical Structures and Conformation-Adjustable Fullerenes Binding, Chem. Eur. J. 2023, e202301955.


R. Yuan, L. Liu, B. Yin*, L. Xu, M. Zhou, Y. Rao, J. Song*,  β-Unsubstituted 5-monoazaporphyrin and its derivatives, J. Porphyrins Phthalocyanines. doi: 10.1142/S1088424623501079.



H. Shu, M. Guo, M. Wang, S. Fan, M. Zhou*, L. Xu, Y. Rao, A. Osuka, J. Song*, Rhodium-Catalyzed [5 + 2] Annulation of Pyrrole Appended BODIPYs: Access to Azepine-Fused BODIPYs, Org. Lett. 2023, 25, 1817.


L. Wen, X. Cao, S. Lee, L. Xu, Y. Rao , S. Kang, D. Kim, A. Osuka , J. Song*, Aromatic-bridged and meso-meso-linked BF2-smaragdyrin dimers exhibit fast decays in polar solvents by symmetry-breaking charge transfer, Commun. Chem. 2023, 6, 25.


M. Ye, F. Deng, L. Xu, Y. Rao, B. Yin, M. Zhou, R. Kurosaki, N. Aratani, A. Osuka, and J. Song*, A Quadruply Bridged Non-Offset Face-to-Face Porphyrin Dimer and Cross-Shaped Pentameric Porphyrin Tapes Based on 2,7,12,17-Tetrakis(pinacolatoboryl) NiII Porphyrin, Angew. Chem. Int. Ed. 2023, 62,  e202300260.


P. Lin, S. Xiong, Y. Rao, L. Xu, M. Zhou, B. Yin, A. Osuka, and J. Song*, Heptagon/Octagon-Fused Diporphyrins or Spiro-Pentagon-Bridged Dichlorin from p-Terphenylene-Bridged Diporphyrin, Chem. Asian J. 2023, 18, e202300018.


X. Ge, Y. Rao, L.Xu, M. Zhou, R. Kurosaki, N. Aratani, A. Osuka, J. Song*, Bottom-Up Synthesis of Multiply Fused PdII Anthriporphyrinoids,ACS Cent. Sci. 2022, 8, 1627.


L. Liu, F. Zhang, L. Xu, M. Zhou, B. Yin, T. Tanaka, A. Osuka*, J Song*, m-Benziporphyrin(1.1.0.0)s as a Rare Example of Ring-Contracted Carbaporphyrins with Metal-Coordination Ability: Distorted Coordination Structures and Small HOMO-LUMO Gaps, Chem. Eur. J. 2023, 29, e202203517.


W. Deng, Y. Liu, D. Shimizu, T. Tanaka, A. Nakai, Y. Rao, L. Xu, M. Zhou, A. Osuka* and J. Song*, Facile Formation of Stable Neutral Radicals and Cations from [22]Smaragdyrin BF2 Complexes , Chem.Eur. J. 2023, 29, e202203484.


S. Fan†, Z. Tan†, M. Liang†, M. Zhou*, Y. Rao, L. Xu, A. Osuka*, J. Song*, Synthesis of 2,2’-biphenyl-fusedporphyrins: installation of directlyfused seven-membered ring, J. Porphyrins Phthalocyanines. 2022,10.1142/S1088424622500663.


B. Yin,  F. Deng,  W. Zhou, Y. Rao,  L. Xu,  M. Zhou, A. Osuka, J. Song*, PdII and NiII Complexes of Earring Porphyrins with Distorted Coordination Geometries, Asian J. Org. Chem. 2022, 11, e202200556.


L. Liu, J. Kim, L. Xu, Y. Rao, M. Zhou, B. Yin, J. Oh, D. Kim*, A. Osuka*, J. Song*, Synthesis of Subporphyrin Free Bases, Angew. Chem. Int. Ed. 2022, 61, e202214342.


B. Yin, Y. Liu, Y. Rao, L. Xu, M. Zhou, A. Osuka, J. Song*, Earring Porphyrins Bearing 1,9-Di(pyrid-2-yl)dipyrromethene Unit and Their BODIPY Conjugates, ChemistrySelect. 2022, 7, e202203055.


J. Rong, Y. Wu, X. Ji, T. Zhao, B. Yin, Y. Rao, M. Zhou, A. Osuka, L Xu*, J Song*,  Porphyrinatonickel(II)–Cyclopentene and Porphyrinatonickel(II)–Cyclopentadiene Hybrids: Zirconacyclopentadiene-Mediated Syntheses, Structures, and Mechanistic Study, Org. Lett. 2022, 24, 6128.


H. Shu, M. Guo, M. Wang, M. Zhou,* B. Zhou, L. Xu, Y. Rao, B. Yin, A. Osuka, and J. Song*, Efficient Synthesis of Multiply Seven-Membered-Ring Fused Porphyrins by Rhodium-Catalyzed [5+2] Annulation, Angew. Chem. Int. Ed. 2022, 61, e202209594.

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Y. Liu, D. Xie, Y. Rao, L. Xu, M. Zhou, A. Osuka, and J. Song*, Fused Hybrids of a [22]Smaragdyrin BF2-Complex with a NiII Porphyrin, Angew. Chem. Int. Ed. 2022, 61, e202206601.

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Y. Rao, L. Xu, M. Zhou, B. Yin, A. Osuka,* and J. Song*, Expanded Azaporphyrins Consisting of Multiple BODIPY Units: Global Aromaticity and High Affinities Towards Alkali Metal Ions, Angew. Chem. Int. Ed. 2022, 61, e202206899.

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F. Li , K. Wang, Y. Rao, L. Xu, A. Osuka, J. Song*,  Conformationally restricted and three-dimensionally extended carbazole-incorporating expanded porphyrinoids, Org. Chem. Front., 2022, 9, 4798.

Graphical abstract: Conformationally restricted and three-dimensionally extended carbazole-incorporating expanded porphyrinoids


Y. Wu, T. Zhao, J. Rong, Y. Rao, M. Zhou, B. Yin, X. Ni, A. Osuka, L. Xu* and J. Song*, Low-Valent Zirconocene-mediated Synthesis of Porphyrin(2.1.2.1)s and Its Extension to Synthesis of a Porphyrin(2.1.2.1) Nanobarrel, Angew. Chem. Int. Ed., 2022, 61, e202201327.

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Z. Zhang, B. Wen, Y. Rao, L. Xu, A. Osuka, J. Song* Meso‐Monoaryl‐Substituted Neo‐confused Calixsmaragdyrins and Meso‐monoaryl Substituted Smaragdyrins: Synthesis, Structures and Properties, ChemistrySelect , 2022, 7, e202200619.

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K. Wang, B. Xiao, L. Xu, M. Zhou, T. Tanaka, A. Osuka, J. Song*,  Nitrogen-bridged Ni(II) porphyrinoid trimers with a central quinodiimine unit, Chinese Chemical Letters, 2022, 33, 4545.


B. Xiao, X. Huang, Y. Rao, L. Xu, B. Yin, A. Osuka, J. Song*, Axially Arylene-bridged “Dumbbell” B(III)-Subporphyrin Dimers and a Tetrameric Subporphyrin Nanocage, Chem. Asian J. 2022, 17, e202101406.


K. Wang, P. Liu, F. Zhang, L. Xu, M. Zhou, A. Nakai, K. Kato, K. Furukawa, T. Tanaka, A. Osuka, J. Song,* A Robust Porphyrin-Stabilized Triplet Carbon Diradical, Angew. Chem. Int. Ed. 2021, 60, 7002.

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M. Liang, L. Zi, F. Cheng, Y. Rao, L. Xu, M. Zhou*, J. Song*, Phenazine-Bridged Ni(II) Porphyrin Dimers and Its Oxidative Fusion, J. Porphyrins Phthalocyanines. 2021, 25, 1086.


Y. Fan, Z. Zeng, H. Shu, M. Zhou*, L. Xu, Y. Rao, T. Gu , X. Liang, W. Zhu, J. Song*,  Two- and Three-Dimensional β,β′-N-Heterocycle Fused Porphyrins: Concise Construction, Singlet Oxygen Production and Electro-Catalytic Hydrogen Evolution Reaction,  Org. Chem. Front. 2021, 8, 6080.


P. Jiang, T. Zhao, J. Rong, B. Yin, Y. Rao, M. Zhou, L. Xu, J. Song*, Multi-(phenylthio)porphyrinato Ni(II) Compounds: Synthesis, Structures and Properties. Chinese Chemical Letters, 2021, 32, 2562

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B. Zhou, M. Guo, Q. Pan, M Zhou*, L. Xu, Y. Rao, K. Wang, B. Yin, J. Zhou, J. Song*, Rhodium-catalyzed Annulation of Pyrrole Substituted BODIPYs with Alkynes to Access π-Extended Polycyclic Heteroaromatic Molecules and NIR Absorption,  Org. Chem. Front. 2021, 8, 868.

Graphical abstract: Rhodium-catalyzed annulation of pyrrole substituted BODIPYs with alkynes to access π-extended polycyclic heteroaromatic molecules and NIR absorption


L. Liu, Z. Hu, F. Zhang, Y. Liu, L. Xu, M. Zhou, T. Tanaka, A. Osuka, J. Song*, Benzene- and Pyridine-Incorporated Octaphyrins with Different Coordination Modes Toward two Pd(II ) Centers, Nat. Commun. 2020, 11, 6206.

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K. Wang, A. Osuka, J Song*, Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays, ACS Cent. Sci. 2020, 6, 2159.


Y. Li, M. Zhou, L. Xu, B. Zhou, Y. Rao, H. Nie, T. Gu, J. Zhou , X. Liang, B. Yin, W. Zhu, A. Osuka, J. Song*, Simultaneous Implementation of N-Heterocycle-Fused Bridge and Modified Pyrrole Unit on Ni(II) Porphyrin Dimers, Org. Lett. 2020, 22, 6001.


M. Liang, Y. Li, M. Zhou, Y. Rao, B. Yin, L. Xu, T. Gu, X. Liang, W. Zhu, D. Yu, S. Liu, J. Song*, Synthesis and Characterization of Porphyrin–Pyrene Hybrids, J. Porphyrins Phthalocyanines. 2020, 24, 278.


Y. Rao, W. Zhou, L. Xu, M. Zhou, B Yin, T. Tanaka, A. Osuka, J. Song*, Singly and Doubly Neo-Confused Smaragdyrins, J. Am. Chem. Soc., 2019, 141, 18836.


T. Wu, T. Kim, B. Yin, K. Wang, L. Xu, M. Zhou, D. Kim, J. Song*, Carbazole-containing Porphyrinoid and Its Oligomers, Chem. Commun. 2019, 55, 11454.

Graphical abstract: Carbazole-containing porphyrinoid and its oligomers


L. Wu, F. Li, Y. Rao, B. Wen, L. Xu, M. Zhou, T. Tanaka, A. Osuka, J. Song*, Synthesis, Structures, and Near‐IR Absorption of Heterole‐Fused Earring Porphyrins, Angew. Chem. Int. Ed. 2019, 58, 8124.

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D. Xie, Y. Liu, Y. Rao, G. Kim, M. Zhou, D. Yu, L. Xu, B. Yin, S. Liu, T. Tanaka, N. Aratani, A. Osuka, Q. Liu, D. Kim,* and J. Song*, meso-Triaryl-Substituted Smaragdyrins: Facile Aromaticity Switching , J. Am. Chem. Soc., 2018, 140, 16553.


H. Guan, M. Zhou, B. Yin, L. Xu, J. Song*,  Synthesis and Characterization of π-Extended "Earring" Subporphyrins, Beilstein J. Org. Chem. 2018, 14, 1956.

[1860-5397-14-170-i1]


Y. Jia, L. Xu, B. Yin, M. Zhou, J. Song*Synthesis and Characterization of meso-to-meso Directly Linked Porphyrin-Diazaporphyrin Triads, J. Porphyrins Phthalocyanines. 2018, 22, 2.


B. Yin , X. Liang , W. Zhu , L. Xu , M. Zhou , J. Song*β to β Terpyridylene–Bridged Porphyrin NanoringsChinese Chemical Letters, 2018, 29, 99. 


L. Xu, B. Wen, G. Kim, T. Kim, F. Chen, M. Zhou, L. Xu, T. Tanaka, B. Yin, A. Osuka, D. Kim* and J. Song*, Strategic Construction of Directly Linked Porphyrin-BODIPY Hybrids, Angew. Chem. Int. Ed. 2017, 56, 12322.

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 Y. Rao, T. Kim, K. H. Park, F. Peng, L. Liu, Y. Liu, B. Wen, S. Liu, S. R. Kirk, L. Wu, B. Chen, M. Ma, M. Zhou, B. Yin, Y. Zhang, D. Kim*, J. Song*, π-extened earring porphyrins with multiple cavities and near infrared absorptions, Angew. Chem. Int. Ed. 2016, 55, 6438.

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 H. Cai, K. Fujimoto, J. M. Lim, C. Wang, W. Huang, Y. Rao, S. Zhang, H. Shi, B. Yin, B. Chen, M. Ma, J. Song*, D. Kim*, A. Osuka*, synthesis of β-to-β direct linked porphyrin arrys with large electronic interactions: branched and cyclic oligomers, Angew. Chem. Int. Ed. 2014, 53, 11088.

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J. Song, N. Aratani, H. Shinokubo, and A. Osuka, A Porphyrin Nanobarrel that encapsulate C60, J. Am. Chem. Soc. 2010, 132, 16356.


J. Song, N. Aratani, J. Heo, D. Kim, H. Shinokubo, and A. Osuka, Directly Pd(II)-Bridged Porphyrin belts with Remarkable Curveatures, J. Am. Chem. Soc. 2010, 132, 11868.


J. Song, N. Aratani, P. Kim, D. Kim, H. Shinokubo, and A. Osuka, Porphyrin LEGO block strategy to construct Directly meso-β Doubly linked porphyrin rings, Angew. Chem. Int. Ed. 2010, 49, 3617 (Selected as Synfacts 2010, 7, 0776) .

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J. Song, S. Y. Jang, S. Yamaguchi, J. Sankar, S. Hiroto, N. Aratani, J-Y. Shin, S. Easwaramoort hi, K. S. Kim, D. Kim, H. Shinokubo, and A.Osuka, 2,5-Thionylene-Bridged Triangular and Linear Porphyrin trimers, Angew. Chem. Int. Ed. 2008, 47, 6004.

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