Hexakis(m-phenylene ethynylene) Macrocycles with Multiple H-Bonding Side Chains and Modified Cavities: Altered Stacking Strength and Persistent Tubular Assembly

Yulong Zhong; Qiuhua Wang; Yi Yang; Zhonglin Lu; Lan He; Bing Gong

doi:10.1021/acs.orglett.6b00718

Hexakis(m-phenylene ethynylene) Macrocycles with Multiple H-Bonding Side Chains and Modified Cavities: Altered Stacking Strength and Persistent Tubular Assembly

Org Lett. 2016 May 6;18(9):2094-7. doi: 10.1021/acs.orglett.6b00718. Epub 2016 Apr 13.

Authors

Yulong Zhong¹, Qiuhua Wang¹, Yi Yang¹, Zhonglin Lu¹, Lan He^{1

2}, Bing Gong^{1

3}

Affiliations

¹ College of Chemistry, Beijing Normal University , Beijing 100875, China.
² National Institute for Food and Drug Control , Beijing 100050, China.
³ Department of Chemistry, The State University of New York at Buffalo , Buffalo, New York 14260, United States.

PMID: 27074740
DOI: 10.1021/acs.orglett.6b00718

Abstract

Hexakis(m-phenylene ethynylene) macrocycles 1 bearing multiple hydrogen-bonding side chains and containing inner cavities modified with different functional groups are synthesized based on Pd-catalyzed (Sonogashira) coupling of monomeric building blocks to trimeric precursors that are recombined and coupled to give macrocycles with different substitution patterns of inward-pointing groups. Examining four representative macrocycles indicates that they all undergo the same helical tubular assembly previously observed for macrocycle 1a but with different stacking strengths.

Publication types

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