1,3-Dithiole-2-one-Fused Subphthalocyanine and Subporphyrazine: Synthesis and Properties Arising from the 1,3-Dithiole-2-one Units

Yemei Wang, Koya Uchihara, Shigeki Mori, Hiroyuki Furuta, Soji Shimizu

研究成果: ジャーナルへの寄稿記事

抄録

Subphthalocyanine (SubPc) and its benzo ring-removed analogue, subporphyrazine (SubPz), bearing 1,3-dithiole-2-one (S2CO) groups as a new class of substituents were synthesized. In addition to the perturbed optical properties due to the presence of electron-withdrawing S2CO units, the deep bowl-shaped structure of the SubPz derivative allowed concave-convex interaction to form a unique co-crystal structure with C60. Finally, using the reactivity of the peripheral S2CO units, S2CO-fused SubPc was successfully converted into tetrathiafulvalene (TTF)-annulated SubPc in a yield higher than that of the direct synthesis from a TTF-fused phthalonitrile.

元の言語英語
ジャーナルOrganic Letters
DOI
出版物ステータス印刷前のE-pub - 4 12 2019

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Bearings (structural)
reactivity
analogs
optical properties
crystal structure
rings
synthesis
electrons
Optical properties
Crystal structure
interactions
Electrons
Derivatives
tetrathiafulvalene

これを引用

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title = "1,3-Dithiole-2-one-Fused Subphthalocyanine and Subporphyrazine: Synthesis and Properties Arising from the 1,3-Dithiole-2-one Units",
abstract = "Subphthalocyanine (SubPc) and its benzo ring-removed analogue, subporphyrazine (SubPz), bearing 1,3-dithiole-2-one (S2CO) groups as a new class of substituents were synthesized. In addition to the perturbed optical properties due to the presence of electron-withdrawing S2CO units, the deep bowl-shaped structure of the SubPz derivative allowed concave-convex interaction to form a unique co-crystal structure with C60. Finally, using the reactivity of the peripheral S2CO units, S2CO-fused SubPc was successfully converted into tetrathiafulvalene (TTF)-annulated SubPc in a yield higher than that of the direct synthesis from a TTF-fused phthalonitrile.",
author = "Yemei Wang and Koya Uchihara and Shigeki Mori and Hiroyuki Furuta and Soji Shimizu",
year = "2019",
month = "4",
day = "12",
doi = "10.1021/acs.orglett.9b00752",
language = "English",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",

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TY - JOUR

T1 - 1,3-Dithiole-2-one-Fused Subphthalocyanine and Subporphyrazine

T2 - Synthesis and Properties Arising from the 1,3-Dithiole-2-one Units

AU - Wang, Yemei

AU - Uchihara, Koya

AU - Mori, Shigeki

AU - Furuta, Hiroyuki

AU - Shimizu, Soji

PY - 2019/4/12

Y1 - 2019/4/12

N2 - Subphthalocyanine (SubPc) and its benzo ring-removed analogue, subporphyrazine (SubPz), bearing 1,3-dithiole-2-one (S2CO) groups as a new class of substituents were synthesized. In addition to the perturbed optical properties due to the presence of electron-withdrawing S2CO units, the deep bowl-shaped structure of the SubPz derivative allowed concave-convex interaction to form a unique co-crystal structure with C60. Finally, using the reactivity of the peripheral S2CO units, S2CO-fused SubPc was successfully converted into tetrathiafulvalene (TTF)-annulated SubPc in a yield higher than that of the direct synthesis from a TTF-fused phthalonitrile.

AB - Subphthalocyanine (SubPc) and its benzo ring-removed analogue, subporphyrazine (SubPz), bearing 1,3-dithiole-2-one (S2CO) groups as a new class of substituents were synthesized. In addition to the perturbed optical properties due to the presence of electron-withdrawing S2CO units, the deep bowl-shaped structure of the SubPz derivative allowed concave-convex interaction to form a unique co-crystal structure with C60. Finally, using the reactivity of the peripheral S2CO units, S2CO-fused SubPc was successfully converted into tetrathiafulvalene (TTF)-annulated SubPc in a yield higher than that of the direct synthesis from a TTF-fused phthalonitrile.

U2 - 10.1021/acs.orglett.9b00752

DO - 10.1021/acs.orglett.9b00752

M3 - Article

C2 - 30977374

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -