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
N1 - Funding Information:
This work was supported by Grants-in-Aid for Young Scientists A (JSPS KAKENHI Grant JP26708003) and Scientific Research on Innovative Area, “π-System Figuration: Control of Electron and Structural Dynamism for Innovative Functions (No. 2601)” (JSPS KAKENHI Grant JP17H05160).
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/5/3
Y1 - 2019/5/3
N2 - Subphthalocyanine (SubPc) and its benzo ring-removed analogue, subporphyrazine (SubPz), bearing 1,3-dithiole-2-one (S 2 CO) groups as a new class of substituents were synthesized. In addition to the perturbed optical properties due to the presence of electron-withdrawing S 2 CO units, the deep bowl-shaped structure of the SubPz derivative allowed concave-convex interaction to form a unique co-crystal structure with C 60 . Finally, using the reactivity of the peripheral S 2 CO units, S 2 CO-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 (S 2 CO) groups as a new class of substituents were synthesized. In addition to the perturbed optical properties due to the presence of electron-withdrawing S 2 CO units, the deep bowl-shaped structure of the SubPz derivative allowed concave-convex interaction to form a unique co-crystal structure with C 60 . Finally, using the reactivity of the peripheral S 2 CO units, S 2 CO-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.
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U2 - 10.1021/acs.orglett.9b00752
DO - 10.1021/acs.orglett.9b00752
M3 - Article
C2 - 30977374
AN - SCOPUS:85065211895
SN - 1523-7060
VL - 21
SP - 3103
EP - 3107
JO - Organic Letters
JF - Organic Letters
IS - 9
ER -