6,7-Bismethoxy-2,11-dihydroxytetraphenylene Derived Macrocycles: Synthesis, Structures, and Complexation with Fullerenes

Chun-Lin Deng; Xiao-Dong Xiong; David T W Chik; Zongwei Cai; Xiao-Shui Peng; Henry N C Wong

doi:10.1002/asia.201500689

6,7-Bismethoxy-2,11-dihydroxytetraphenylene Derived Macrocycles: Synthesis, Structures, and Complexation with Fullerenes

Chem Asian J. 2015 Nov;10(11):2342-6. doi: 10.1002/asia.201500689. Epub 2015 Aug 11.

Authors

Chun-Lin Deng¹, Xiao-Dong Xiong¹, David T W Chik², Zongwei Cai², Xiao-Shui Peng^{1

3}, Henry N C Wong^{4

5}

Affiliations

¹ Department of Chemistry, State Key Laboratory of Synthetic Chemistry, Center of Novel Functional Molecules, and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.
² Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong SAR, China.
³ Shenzhen Center of Novel Functional Molecules & Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No.10, Second Yuexing Road, Shenzhen, 518507, China.
⁴ Department of Chemistry, State Key Laboratory of Synthetic Chemistry, Center of Novel Functional Molecules, and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China. hncwong@cuhk.edu.hk.
⁵ Shenzhen Center of Novel Functional Molecules & Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No.10, Second Yuexing Road, Shenzhen, 518507, China. hncwong@cuhk.edu.hk.

PMID: 26211744
DOI: 10.1002/asia.201500689

Abstract

6,7-Bismethoxy-2,11-dihydroxytetraphenylene (1), a novel building block of tetraphenylene-derived macrocycles, was synthesized via palladium-catalyzed cross-coupling reactions and characterized by X-ray diffraction. The relevant macrocyclic hosts derived from 1 have well-defined structures with fixed conformations both in solution and solid state. They showed efficient and unique properties toward complexation with fullerenes C60 and C70 in toluene.

Keywords: fullerenes; host-guest chemistry; macrocycles; synthesis; tetraphenylene.

Publication types

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

MeSH terms

Catalysis
Crystallography, X-Ray
Fullerenes / chemistry*
Macrocyclic Compounds / chemical synthesis
Macrocyclic Compounds / chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Palladium / chemistry
Terphenyl Compounds / chemical synthesis*
Terphenyl Compounds / chemistry

Substances

Fullerenes
Macrocyclic Compounds
Terphenyl Compounds
Palladium