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Well-Defined Two Dimensional Covalent Organic Polymers Volume 6 Number 11 21 March 2015 Pages 1885–2152 Polymer Chemistry www.rsc.org/polymers ISSN 1759-9954 REVIEW ARTICLE Liming Dai et al. Well-defi ned two dimensional covalent organic polymers: rational design, controlled syntheses, and potential applications Polymer Chemistry View Article Online REVIEW View Journal | View Issue Well-defined two dimensional covalent organic polymers: rational design, controlled syntheses, Cite this: Polym. Chem., 2015, 6, 1896 and potential applications Zhonghua Xiang,a Dapeng Caob and Liming Dai*a Two-dimensional (2D) covalent organic polymers (COPs) and derivatives hold great potential for a large variety of applications, including gas storage, sensing, energy conversion and storage, and electrocatalysis. Moreover, 2D COPs offer excellent opportunities for fundamental study on an exciting class of new poly- meric materials with unique 2D structures and novel properties. However, the design and synthesis of Received 10th October 2014, well-defined 2D COPs remain a big challenge. In this article, we review recent progress on 2D COPs and Accepted 7th January 2015 their derivatives. Some concepts on the rational design and syntheses of well-defined 2D COPs and their DOI: 10.1039/c4py01383b derivatives are discussed, along with their potential applications as well as the perspectives and challenges www.rsc.org/polymers in this emerging field. 1. Introduction Synthetic polymers exhibit a wide range of useful properties that can influence most aspects of our modern life. Various aCenter of Advanced Science and Engineering for Carbon (Case4Carbon), polymerization methods have been devised to produce macro- Department of Macromolecular Science and Engineering, Case Western Reserve molecules of different topologies (e.g., linear, branched) with University, 10900 Euclid Avenue, Cleveland, OH 44106, USA. well-defined structures and properties.1 However, the synthesis E-mail: [email protected] bState Key Lab of Organic–Inorganic Composites, Beijing University of Chemical of two-dimensional covalent organic polymers (2D COPs) and 2,3 Technology, Beijing 100029, P.R. China derivatives is a recent development in the polymer field. Published on 23 January 2015. Downloaded by CASE WESTERN RESERVE UNIVERSITY 18/04/2015 19:06:20. Zhonghua Xiang joined Beijing Dapeng Cao is a professor and University of Chemical Technol- director of the Division of Mole- ogy (BUCT) as a professor in the cular and Materials Simulation, Department of Chemical Engin- State Key Lab for Organic– eering. He is also the director of Inorganic Composites at Beijing the Molecular Energy Materials University of Chemical Technol- R&D Center in the State Key Lab ogy (BUCT). He received his of Organic–Inorganic Composites Ph.D. from BUCT in 2002, and at BUCT. Dr Xiang received his was a research scientist at Nano- Ph.D. degree from BUCT in June Materials Technology Pte Ltd in 2013 and was a postdoctoral Singapore (2002–2003) and a fellow in the Department of postdoctoral researcher at the Zhonghua Xiang Macromolecular Science and Dapeng Cao University of California, River- Engineering at Case Western side (2003–2005). His research Reserve University (2013–2014). His current scientific interests are interests are focused on the targeted synthesis of porous covalent- focused on the design & synthesis of covalent-organic polymers organic polymers and energy conversion and storage materials (COPs) for clean energy application. related to fuel cells, supercapacitors and solar cells. He has pub- lished more than 180 articles in academic journals such as Angew. Chem. Int. Ed., Adv. Mater., Energy Environ. Sci. and ACS Nano. 1896 | Polym. Chem.,2015,6,1896–1911 This journal is © The Royal Society of Chemistry 2015 View Article Online Polymer Chemistry Review The recent discovery of graphene has caused a surge of mentioned that 3D crystalline or amorphous COP materials interest in the research and development of 2D materials and have also been extensively designed and synthesized from – opened up a new era for 2D COPs.3 6 The 2D single atomic some of the rigid monomers mentioned in this review with – thick carbon sheet of graphene is a building block for carbon various polymerization methods.35 39 Since the development materials of all other dimensionalities, including 0D bucky- of 3D COP materials has been recently reviewed,19,39 we focus balls, 1D nanotubes, and 3D graphite. Having a one-atom- on 2D COPs in this article. thick layer of sp2-bonded 2D honeycomb lattice carbon, gra- phene possesses a high aspect ratio (the ratio of lateral size to thickness), large surface,4 excellent charge carrier mobility,5,6 2. Rational design – and good mechanical properties.7 9 The unique structure and To make 2D COPs with a well-defined structure, the first properties make graphene and its derivatives very promising important step is to design molecular geometries of the build- for a wide range of potential applications, including elec- ing blocks. Typically, rigid building blocks are used to prevent tronics,7,8 sensors,9,10 energy storage4,12 and conversion,4,11,13 14 15 the networks from collapsing and to construct the networks in biomedical diagnosis, and electrocatalysis. Similar to gra- – free space in an efficient manner.37 41 To this end, chemists phene and its derivatives, 2D COPs with precisely-controlled often employ aromatic monomers and their derivatives, linked molecular structures and holes incorporating metals (i.e.,Fe, either directly together or through other rigid molecular lin- Co, Mn) or not incorporating them, have recently been demon- kages.16 Fig. 1 schematically shows six typical building blocks strated to show potentials for a wide variety of applications, (i.e.,B,B,B,B ,B and B ), along with possible COPs including energy conversion and storage, gas storage and sep- 2 T 3 4a 4b 6 – resulting from them. The arrows in all of the different types of aration, sensing, and catalysis, to name a few.3,16 18 As a vital building blocks refer to the active sites for connecting with class of COPs with predesigned skeletons and nanopores of other building blocks, while the core in each of the building atomic precision, covalent organic frameworks (COFs) have – blocks represents the various backbones to be built into the rapidly developed19,20 25 since the appearance of the first resulting 2D COPs via self-condensation or cross coupling. As report on COF in 2005.26 Owing to their high porosity, well- can be seen in Fig. 1, symmetric building blocks B and B defined molecular structure, and multi-functionalities, COFs 3 6 tend to form the honeycomb COP P (Fig. 1c) and P (Fig. 1f), show great promise for various applications, ranging from gas 3 6 respectively. The cross building block B can form the 2D storage through catalysis to optoelectronics.16 Since the 4a Kagome network P and diamond polymer P (Fig. 1d), research and development of graphene have been extensively 4a-1 4a-2 – and the symmetric cross building block B forms square 2D reviewed,15,16,27 34 we mainly focus in this review article on 4b polymer P (Fig. 1e). Compared with the above building COPs and derivatives by summarizing recent important devel- 4b blocks, the T-shaped building block B is most complicated, opments in this emerging field of active research and present- T from which four possible 2D COPs can form, depending on ing critical issues, challenges, and perspectives. Some brief the directions for each of the building blocks to point to discussions on potential applications of COPs and their deriva- during the coupling (Fig. 1b). On the other hand, the simplest tives are also given in the sections as appropriate. It should be linear building block B2 (Fig. 1a) alone cannot ensure the for- mation of 2D COP, but can be incorporated into the COPs formed by other building blocks to extend the 2D topology. Published on 23 January 2015. Downloaded by CASE WESTERN RESERVE UNIVERSITY 18/04/2015 19:06:20. The molecular structures for some representative building Liming Dai is a Kent Hale Smith blocks are summarized in Fig. 2. To date, there are many Professor in the Department of reported 2D polymers constructed from B2,B3,B4a,B4b and Macromolecular Science and – B .16,19,32,40 43 However, 2D COPs based on the T-shape build- Engineering at Case Western 6 ing block B have been rarely reported, presumably because it Reserve University. He is also the T is difficult to form the three 90°-angled active sites using the director of the Center of rigid aromatic moieties due to their strong steric hindrance.44 Advanced Science and Engineer- Nevertheless, certain T-shaped macromolecules have been con- ing for Carbon. Before joining structed through the coordination of metal ions with organic CWRU, he was an associate pro- – linkers,45 47 though it is still a challenge to design and syn- fessor of polymer engineering at thesize T-shaped organic building blocks in general. University of Akron and the Wright Brothers Institute Liming Dai Endowed Chair Professor at Uni- 3. Controlled syntheses versity of Dayton. He is a Fellow of the Royal Society of Chemistry and Fellow of the American Insti- 3.1 Solution condensations tute for Medical and Biological Engineering. His expertise covers To synthesize the rationally designed 2D COPs, various the synthesis, functionalization and fabrication of conjugated solvothermal methods, including the boronic acid-based con- polymers and carbon nanomaterials for energy- and bio-device densation,38,48 Schiff-base reaction,49,50 cyclotrimerization,51,52 applications. phenazine ring fusion reaction,53 Suzuki cross-coupling This journal is © The Royal Society of Chemistry 2015 Polym. Chem.,2015,6,1896–1911 | 1897 View Article Online Review Polymer Chemistry Fig. 1 Main building blocks for 2D COPs, and strategies for 2D polymerization. (a) A linear building block B2, which can be combined with other building blocks in (b), (c), (d), (e) and (f) for lengthening the structures of 2D COPs.
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