Thiacalix[n]thiophene and thiacalix[n]dithienothiophene: Facile synthesis, molecular structures, and complexation with C₆₀ and C₇₀

Abstract

A series of Thiacalix[n]thiophene and Thiacalix[n]dithienothiophene (Thiacalix[n]DTT) have been synthesized by a facile palladium-catalyzed coupling reactions using dibromothieno- or dibromoDTT derivatives with (ⁿBu₃Sn)₂S in good yield. X-ray analysis of thiacalix[4]- and thiacalix[5]DTT revealed its symmetrical structure having alternate and folding arrangement of DTT units, respectively. Furthermore, thiacalix[n]DTT undergoes complexation with C₆₀ and C₇₀ both in solution and in the solid state.

Graphical Abstract

Keywords:

• Thiacalix[n]arene
• thiophene
• dithienothiophene
• sulfur containing heterocycle

Acknowledgement

The authors would like to thank Dr. Masafumi Ueda (Kitasato University) and Dr. Kenji Yoza (Bruker AXS.) for helpful discussions.

Additional information

Funding

The authors acknowledge financial support by JSPS KAKENHI (grant nos. JP20438120 and JP16K17871) and research grant from Kitasato Research Center for Environment Science.