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

doi:10.1021/acs.orglett.9b00752

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

Org Lett. 2019 May 3;21(9):3103-3107. doi: 10.1021/acs.orglett.9b00752. Epub 2019 Apr 12.

Authors

Yemei Wang¹, Koya Uchihara¹, Shigeki Mori², Hiroyuki Furuta^{1

3}, Soji Shimizu^{1

3}

Affiliations

¹ Department of Chemistry and Biochemistry, Graduate School of Engineering , Kyushu University , Fukuoka 819-0395 , Japan.
² Advanced Research Support Center (ADRES) , Ehime University , Matsuyama 790-8577 , Japan.
³ Center for Molecular Systems (CMS) , Kyushu University , Fukuoka 819-0395 , Japan.

PMID: 30977374
DOI: 10.1021/acs.orglett.9b00752

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.

Publication types

Research Support, Non-U.S. Gov't