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      The Supramolecular Chemistry of Cycloparaphenylenes and Their Analogs

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          Abstract

          Cycloparaphenylenes (CPPs) and their analogs have recently attracted much attention due to their aesthetical structures and optoelectronic properties with radial π-conjugation systems. The past 10 years have witnessed a remarkable advancement in CPPs research, from synthetic methodology to optoelectronic investigations. In this present minireview, we highlight the supramolecular chemistry of CPPs and their analogs, mainly focusing on the size-selective encapsulation of fullerenes, endohedral metallofullerenes, and small molecules by these hoop-shaped macrocycles. We will also discuss the assembly of molecular bearings using some belt-persistent tubular cycloarylene molecules and fullerenes, photoinduced electron transfer properties in supramolecular systems containing carbon nanohoop hosts and fullerene guests, as well as the shape recognition properties for structure self-sorting by using dumbbell-shaped dimer of [60]fullerene ligand. Besides, the supramolecular complexes with guest molecules other than fullerenes, such as CPPs themselves, iodine, pyridinium cations, and bowl-shaped corannulene, are also discussed.

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          para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property.

          Condensation of 1,4-dimethoxybenzene (DMB) with paraformaldehyde in the presence of BF3.O(C2H5)2 gave novel para-bridged pentacyclic pillar DMB (DMpillar[5]arene). Moreover, para-bridged pentacyclic hydroquinone (pillar[5]arene) was prepared. Pillar[5]arene formed 1:1 host-guest complexes with dialkyl viologen and alkyl pyridinium derivatives. However, pillar[5]arene did not form complexes with the diadamantyl viologen derivative since a bulky adamantyl group was unable to thread the cavity of pillar[5]arene.
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            Stimuli-responsive supramolecular polymeric materials.

            Supramolecular materials, dynamic materials by nature, are defined as materials whose components are bridged via reversible connections and undergo spontaneous and continuous assembly/disassembly processes under specific conditions. On account of the dynamic and reversible nature of noncovalent interactions, supramolecular polymers have the ability to adapt to their environment and possess a wide range of intriguing properties, such as degradability, shape-memory, and self-healing, making them unique candidates for supramolecular materials. In this critical review, we address recent developments in supramolecular polymeric materials, which can respond to appropriate external stimuli at the fundamental level due to the existence of noncovalent interactions of the building blocks.
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              Supramolecular Polymers: Historical Development, Preparation, Characterization, and Functions.

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                Author and article information

                Contributors
                Journal
                Front Chem
                Front Chem
                Front. Chem.
                Frontiers in Chemistry
                Frontiers Media S.A.
                2296-2646
                09 October 2019
                2019
                : 7
                : 668
                Affiliations
                [1] 1School of Pharmacy, Anhui Medical University , Hefei, China
                [2] 2Hefei National Laboratory for Physical Sciences at the Microscale, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering, University of Science and Technology of China , Hefei, China
                Author notes

                Edited by: De-Xian Wang, Institute of Chemistry (CAS), China

                Reviewed by: Han-Yuan Gong, Beijing Normal University, China; Shixin Fa, Kyoto University, Japan

                *Correspondence: Dapeng Lu ludapeng@ 123456ahmu.edu.cn

                This article was submitted to Supramolecular Chemistry, a section of the journal Frontiers in Chemistry

                Article
                10.3389/fchem.2019.00668
                6794338
                31649920
                6e8eac5d-9a42-4633-8974-dcc9412ad8b3
                Copyright © 2019 Lu, Huang, Wang, Wang, Huang and Du.

                This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

                History
                : 11 August 2019
                : 19 September 2019
                Page count
                Figures: 2, Tables: 0, Equations: 0, References: 70, Pages: 9, Words: 6571
                Funding
                Funded by: National Natural Science Foundation of China 10.13039/501100001809
                Award ID: 21801004
                Categories
                Chemistry
                Mini Review

                supramolecular chemistry,fullerene guest,non-fullerene guest,carbon nanohoop,cycloparaphenylene

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