Aggregation-Induced-Emission-Active Macrocycle Exhibiting Analogous Triply and Singly Twisted Möbius Topologies

Erjing Wang; Zikai He; Engui Zhao; Luming Meng; Christian Schütt; Jacky W Y Lam; Herman H Y Sung; Ian D Williams; Xuhui Huang; Rainer Herges; Ben Zhong Tang

doi:10.1002/chem.201502224

Aggregation-Induced-Emission-Active Macrocycle Exhibiting Analogous Triply and Singly Twisted Möbius Topologies

Chemistry. 2015 Aug 10;21(33):11707-11. doi: 10.1002/chem.201502224. Epub 2015 Jul 14.

Authors

Erjing Wang^{1

2

3}, Zikai He^{1

2}, Engui Zhao^{1

2}, Luming Meng², Christian Schütt⁴, Jacky W Y Lam^{1

2}, Herman H Y Sung², Ian D Williams², Xuhui Huang², Rainer Herges⁵, Ben Zhong Tang^{6

7

8}

Affiliations

¹ HKUST Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park Nanshan, Shenzhen 518057 (China).
² Department of Chemistry, Division of Life Science, State Key Laboratory of Molecular Neuroscience, Institute for Advanced Study, Institute of Molecular Functional Materials, Division of Biomedical Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (China).
³ School of Materials Science and Engineering, Hubei University, No. 368, Youyi Avenue, Wuhan 430062 (China).
⁴ Institute for Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, 24098 Kiel (Germany)iso-kiel.de.
⁵ Institute for Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, 24098 Kiel (Germany)iso-kiel.de. rherges@oc.un.
⁶ HKUST Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park Nanshan, Shenzhen 518057 (China). tangbenz@ust.hk.
⁷ Department of Chemistry, Division of Life Science, State Key Laboratory of Molecular Neuroscience, Institute for Advanced Study, Institute of Molecular Functional Materials, Division of Biomedical Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (China). tangbenz@ust.hk.
⁸ Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640 (China). tangbenz@ust.hk.

PMID: 26177730
DOI: 10.1002/chem.201502224

Abstract

Molecules with Möbius topology have drawn increasing attention from scientists in a variety of fields, such as organic chemistry, inorganic chemistry, and material science. However, synthetic difficulties and the lack of functionality impede their fundamental understanding and practical applications. Here, we report the facile synthesis of an aggregation-induced-emission (AIE)-active macrocycle (TPE-ET) and investigate its analogous triply and singly twisted Möbius topologies. Because of the twisted and flexible nature of the tetraphenylethene units, the macrocycle adjusts its conformations so as to accommodate different guest molecules in its crystals. Moreover, theoretical studies including topological and electronic calculations reveal the energetically favorable interconversion process between triply and singly twisted topologies.

Keywords: aggregation-induced emission; macrocycles; möbius topology; topology flipping.

Publication types

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