Functional Sulfur-Doped Buckybowls and Their Concave-Convex Supramolecular Assembly with Fullerenes

Yu-Min Liu; Dan Xia; Bo-Wei Li; Qian-Yan Zhang; Tsuneaki Sakurai; Yuan-Zhi Tan; Shu Seki; Su-Yuan Xie; Lan-Sun Zheng

doi:10.1002/anie.201606383

Functional Sulfur-Doped Buckybowls and Their Concave-Convex Supramolecular Assembly with Fullerenes

Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13047-13051. doi: 10.1002/anie.201606383.

Authors

Yu-Min Liu¹, Dan Xia¹, Bo-Wei Li¹, Qian-Yan Zhang¹, Tsuneaki Sakurai², Yuan-Zhi Tan³, Shu Seki², Su-Yuan Xie⁴, Lan-Sun Zheng¹

Affiliations

¹ Collaborative Innovation Center of Chemistry for Energy Materials, State Key Laboratory for Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
² Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
³ Collaborative Innovation Center of Chemistry for Energy Materials, State Key Laboratory for Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China. yuanzhi_tan@xmu.edu.cn.
⁴ Collaborative Innovation Center of Chemistry for Energy Materials, State Key Laboratory for Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China. syxie@xmu.edu.cn.

PMID: 27650894
DOI: 10.1002/anie.201606383

Abstract

Buckybowls are fascinating components of supramolecular assemblies owing to their unique bowl-shaped π-surfaces. Herein we present a protocol for the functionalization of a sulfur-doped buckybowl, trithiasumanene, via a brominated intermediate, from which thiolated trithiasumanenes were derived. The curved surface and electron-donating properties of thiolated trithiasumanenes promote their ready assembly with fullerenes to form concave-convex complexes. The supramolecular assembly behavior in solution was investigated by NMR analysis. The structures of supramolecular complexes were unambiguously characterized by crystallography. The crystals of the concave-convex complexes showed high thermal stability and photoconductivity.

Keywords: buckybowls; fullerenes; sulfur; supramolecular assemblies; π interactions.

Publication types

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