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Progress in Chemistry 2019, Vol. 31 Issue (11): 1528-1539 DOI: 10.7536/PC190708 Previous Articles   Next Articles

Photo-Controlled Supramolecular Assemblies Based on Azo Group

Yao-Hua Liu, Yu Liu**()   

  1. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
  • Received: Online: Published:
  • Contact: Yu Liu
  • About author:
    ** E-mail:
  • Supported by:
    National Natural Science Foundation of China(21432004); National Natural Science Foundation of China(21772099); National Natural Science Foundation of China(21861132001)
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Azo compounds are a class of trans-cis(E/Z) photoisomerization compounds which have advantages of simple synthesis, high isomerization rate and efficiency, and resistance to photobleaching. Due to their outstanding photoisomeric properties and ability to form stable inclusion complexes with macrocyclic hosts, azo compounds have shown great potential application in many fields. In this review, we show the design principles, assembly mechanism, application and development of the photo-controlled supramolecular assemblies in topologically morphological regulation, drug delivery, smart materials and so on, which are constructed by host-guest interaction using azo modified cyclodextrin, bis-cyclodextrin bridged by azobenzene, crown ether derivatives, azo aromatic macrocyclic compounds as the hosts or azobenzene or azobenzene derivatives as guests. At the same time, we also discuss the opportunities and challenges of the development of such supramolecular assemblies, and hope to further promote the development of intelligent supramolecular assemblies.

Key words: azo-compounds, photo-stimuli responsiveness, supramolecular self-assembly, host-guest interaction
Fig. 1 a) Several typical macrocyclic hosts and b) azo compounds and their supramolecular assemblies with cyclodextrins[40,41,42]. Reproduced with permission. Copyright 2019, Wiley-VCH.
Fig. 2 Photocontrolled supramolecular assemblies of microtubules[43]. Reproduced with permission. Copyright 2019, Wiley-VCH.
Fig. 3 A half adder based on a photocontrolled [2]rotaxane[50]
Fig. 4 A double INHIBIT logic gate based on a photocontrolled [2]rotaxane[51]
Fig. 5 Photoresponsive heteroternary supramolecular assemblies based on azobenzene, methylviologen and CB[8][73]
Fig. 6 Tunable nanosupramolecular aggregates based on azobenzene and dipeptide[82]. Reproduced with permission. Copyright 2016, Wiley-VCH.
Fig. 7 Photoresponsive supramolecular assembly based on pillar[6]arene and azo compounds[84]. Reproduced with permission. Copyright 2012, American Chemical Society.
Fig. 8 Light-triggered crystallization of a molecular host-guest complex[90]. Reproduced with permission. Copyright 2010, American Chemical Society.
Fig. 9 a) Photocontrolled reversible conversion of nanotube and nanoparticle[97]. Reproduced with permission. Copyright 2015, Wiley-VCH. b) Tunable supramolecular assembly and photoswitchable conversion of 1D and 2D nanostructures[98]. Reproduced with permission. Copyright 2017, Wiley-VCH.
Fig. 10 Photocontrolled morphological conversion and chiral transfer of a snowflake-like supramolecular assembly[110]. Reproduced with permission. Copyright 2019, The Royal Society of Chemistry.
Fig. 11 Phototunable supramolecular catalyst based on crown ether bridged by azobenzene[111]. Reproduced with permission. Copyright 2003, American Chemical Society
Fig. 12 A dual-responsive receptor for aryl dianion encapsulation based on azobenzene[116]. Reproduced with permission. Copyright 2019, American Chemical Society.
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