Synthetic Two-dimensional Organic Structures

Hui Liu; Xiao-Nan Kan; Chen-Yu Wu; Qing-Yan Pan; Zhi-Bo Li; Ying-Jie Zhao

doi:10.1007/s10118-018-2070-6

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Synthetic Two-dimensional Organic Structures

Reviews | Updated：2021-02-18

- Synthetic Two-dimensional Organic Structures
- Chinese Journal of Polymer Science Vol. 36, Issue 4, Pages: 425-444(2018)
- Affiliations：
  
  a.Qingdao University of Science and Technology, Qingdao 266042, China
  b.Centre for Advanced Macromolecular Design, School of Chemical Engineering, The University of New South Wales, Sydney, NSW 2052, Australia
- Author bio：
  
  E-mail zbli@qust.edu.cn (Z.B.L.)
  E-mail yz@qust.edu.cn (Y.J.Z.)
- Funds：
- DOI：10.1007/s10118-018-2070-6
  CLC：
- Received：26 April 2018，
  
  Accepted：21 October 2017，
  
  Online First：20 December 2017，
  
  Published：05 April 2018
- Accepted：
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Hui Liu, Xiao-Nan Kan, Chen-Yu Wu, et al. Synthetic Two-dimensional Organic Structures[J]. Chinese Journal of Polymer Science, 2018, 36(4): 425-444.
DOI：

Hui Liu, Xiao-Nan Kan, Chen-Yu Wu, et al. Synthetic Two-dimensional Organic Structures[J]. Chinese Journal of Polymer Science, 2018, 36(4): 425-444. DOI： 10.1007/s10118-018-2070-6.

摘要

Abstract

Synthetic two-dimensional (2D) polymers have totally different topology structures compared with traditional linear or branched polymers. The peculiar 2D structures bring superior properties. Although

from linear to 2D polymers

the study of these new materials is still in its infancy

they already show potential applications especially in optoelectronics

membranes

energy storage and catalysis

etc. In this review

we summarize the recent progress of the 2D materials from three respects:(1) Chemistry-different types of polymerization reactions or supramolecular assembly to construct the 2D networks were described; (2) Preparation methods-surface science

crystal engineering approaches and solution synthesis were introduced; (3) Functionalization and some early applications.

关键词

Keywords

references

C. E. Boott , A. Nazemi , I. Manners . Synthetic covalent and non-covalent 2D materials . Angew. Chem. Int. Ed. , 2015 . 54 ( 47 ): 13876 - 13894 . DOI: 10.1002/anie.201502009 http://doi.org/10.1002/anie.201502009 .

K. Baek , I. Hwang , I. Roy , D. Shetty , K. Kim . Self-assembly of nanostructured materials through irreversible covalent bond formation . Acc. Chem. Res. , 2015 . 48 ( 8 ): 2221 - 2229 . DOI: 10.1021/acs.accounts.5b00067 http://doi.org/10.1021/acs.accounts.5b00067 .

X. Zhuang , Y. Mai , D. Wu , F. Zhang , X. Feng . Two-dimensional soft nanomaterials:a fascinating world of materials . Adv. Mater. , 2015 . 27 ( 3 ): 403 - 427 . DOI: 10.1002/adma.v27.3 http://doi.org/10.1002/adma.v27.3 .

Z. Xiang , D. Cao , L. Dai . Well-defined two dimensional covalent organic polymers:rational design, controlled syntheses, and potential applications . Polym. Chem. , 2015 . 6 ( 11 ): 1896 - 1911 . DOI: 10.1039/C4PY01383B http://doi.org/10.1039/C4PY01383B .

P. Payamyar , B. T. King , H. C. Ottinger , A. D. Schluter . Two-dimensional polymers:concepts and perspectives . Chem. Commun. , 2016 . 52 ( 1 ): 18 - 34 . DOI: 10.1039/C5CC07381B http://doi.org/10.1039/C5CC07381B .

D. Rodriguez-San-Miguel , P. Amo-Ochoa , F. Zamora . MasterChem:cooking 2D-polymers . Chem. Commun. , 2016 . 52 ( 22 ): 4113 - 4127 . DOI: 10.1039/C5CC10283A http://doi.org/10.1039/C5CC10283A .

S. L. Cai , W. G. Zhang , R. N. Zuckermann , Z. T. Li , X. Zhao , Y. Liu . The organicflatland-recent advances in synthetic 2D organic layers . Adv. Mater. , 2015 . 27 ( 38 ): 5762 - 5770 . DOI: 10.1002/adma.v27.38 http://doi.org/10.1002/adma.v27.38 .

M. Lackinger . On-surface polymerization-a versatile synthetic route to two-dimensional polymers . Polym. Int. , 2015 . 64 ( 9 ): 1073 - 1078 . DOI: 10.1002/pi.2015.64.issue-9 http://doi.org/10.1002/pi.2015.64.issue-9 .

T. Chen , D. Wang , L. J. Wan . Two-dimensional chiral molecular assembly on solid surfaces:formation and regulation . Natl. Sci. Rev. , 2015 . 2 ( 2 ): 205 - 216 . DOI: 10.1093/nsr/nwv012 http://doi.org/10.1093/nsr/nwv012 .

J. W. Colson , W. R. Dichtel . Rationally synthesized two-dimensional polymers . Nat. Chem. , 2013 . 5 453 - 465 . DOI: 10.1038/nchem.1628 http://doi.org/10.1038/nchem.1628 .

Y. Zang , T. Aoki , M. Teraguchi , T. Kaneko , L. Ma , H. Jia . Two-dimensional and related polymers:concepts, synthesis, and their potential application as separation membrane materials . Polym. Rev. , 2015 . 55 ( 1 ): 57 - 89 . DOI: 10.1080/15583724.2014.963235 http://doi.org/10.1080/15583724.2014.963235 .

K. S. Novoselov . Electric field effect in atomically thin carbon films . Science , 2004 . 306 666 - 669 . DOI: 10.1126/science.1102896 http://doi.org/10.1126/science.1102896 .

H. Staudinger . Über Polymerisation . Berichte der deutschen chemischen gesellschaft (a and b series) , 1920 . 53 ( 6 ): 1073 - 1085 . DOI: 10.1002/cber.19200530627 http://doi.org/10.1002/cber.19200530627 .

J. Sakamoto , J. van Heijst , O. Lukin , A. D. Schlüter . Two-dimensional polymers:just a dream of synthetic chemists? Angew . Chem. Int. Ed. , 2009 . 48 1030 - 1069 . DOI: 10.1002/anie.v48:6 http://doi.org/10.1002/anie.v48:6 .

Y. Jin , C. Yu , R. J. Denman , W. Zhang . Recent advances in dynamic covalent chemistry . Chem. Soc. Rev. , 2013 . 42 ( 16 ): 6634 - 6654 . DOI: 10.1039/c3cs60044k http://doi.org/10.1039/c3cs60044k .

S. J. Rowan , S. J. Cantrill , G. R. L. Cousins , J. K. M. Sanders , J. F. Stoddart . Dynamic covalent chemistry . Angew. Chem. Int. Ed. , 2002 . 41 ( 6 ): 898 - 952 . DOI: 10.1002/1521-3773(20020315)41:6<>1.0.CO;2-R http://doi.org/10.1002/1521-3773(20020315)41:6<>1.0.CO;2-R .

S. de Feyter , F. C. de Schryver . Two-dimensional supramolecular self-assembly probed by scanning tunneling microscopy . Chem. Soc. Rev. , 2003 . 32 ( 3 ): 139 - 150 . DOI: 10.1039/b206566p http://doi.org/10.1039/b206566p .

J. A. Elemans , S. Lei , S. de Feyter . Molecular and supramolecular networks on surfaces:from two-dimensional crystal engineering to reactivity . Angew. Chem. Int. Ed. , 2009 . 48 ( 40 ): 7298 - 332 . DOI: 10.1002/anie.v48:40 http://doi.org/10.1002/anie.v48:40 .

J. Michl , T. F. Magnera . Two-dimensional supramolecular chemistry with molecular tinkertoys . Proc. Nat. Acad. Sci. , 2002 . 99 4788 - 4792 . DOI: 10.1073/pnas.052016299 http://doi.org/10.1073/pnas.052016299 .

G. Pawin , K. L. Wong , K. Y. Kwon , L. Bartels . A homomolecular porous network at a Cu(111) surface . Science , 2006 . 313 ( 5789 ): 961 - 962 . DOI: 10.1126/science.1129309 http://doi.org/10.1126/science.1129309 .

J. A. Theobald , N. S. Oxtoby , M. A. Phillips , N. R. Champness , P. H. Beton . Controlling molecular deposition and layer structure with supramolecular surface assemblies . Nature , 2003 . 424 ( 6952 ): 1029 - 1031 . DOI: 10.1038/nature01915 http://doi.org/10.1038/nature01915 .

T. Sirtl , S. Schlögl , A. Rastgoo-Lahrood , J. Jelic , S. Neogi , M. Schmittel , W. M. Heckl , K. Reuter , M. Lackinger . Control of intermolecular bonds by deposition rates at room temperature:hydrogen bonds versus metal coordination in trinitrile monolayers . J. Am. Chem. Soc. , 2013 . 135 ( 2 ): 691 - 695 . DOI: 10.1021/ja306834a http://doi.org/10.1021/ja306834a .

M. O. Blunt , J. C. Russell , M. D. C. Giménez-López , J. P. Garrahan , X. Lin , M. Schröder , N. R. Champness , P. H. Beton . Random tiling and topological defects in a two-dimensional molecular network . Science , 2008 . 322 ( 5904 ): 1077 - 1081 . DOI: 10.1126/science.1163338 http://doi.org/10.1126/science.1163338 .

Z. Shi , N. Lin . Porphyrin-based two-dimensional coordination kagome lattice self-assembled on a Au(111) surface . J. Am. Chem. Soc. , 2009 . 131 ( 15 ): 5376 - 5377 . DOI: 10.1021/ja900499b http://doi.org/10.1021/ja900499b .

D. Kuhne , F. Klappenberger , R. Decker , U. Schlickum , H. Brune , S. Klyatskaya , M. Ruben , J. V. Barth . High-quality 2D metal-organic coordination network providing giant cavities within mesoscale domains . J. Am. Chem. Soc. , 2009 . 131 ( 11 ): 3881 - 3883 . DOI: 10.1021/ja809946z http://doi.org/10.1021/ja809946z .

J. Liu , T. Lin , Z. Shi , F. Xia , L. Dong , P. N. Liu , N. Lin . Structural transformation of two-dimensional metal-organic coordination networks driven by intrinsic in-plane compression . J. Am. Chem. Soc. , 2011 . 133 ( 46 ): 18760 - 18766 . DOI: 10.1021/ja2056193 http://doi.org/10.1021/ja2056193 .

Z. Shi , J. Liu , T. Lin , F. Xia , P. N. Liu , N. Lin . Thermodynamics and selectivity of two-dimensional metallo-supramolecular self-assembly resolved at molecular scale . J. Am. Chem. Soc. , 2011 . 133 ( 16 ): 6150 - 6153 . DOI: 10.1021/ja2010434 http://doi.org/10.1021/ja2010434 .

Z. Shi , N. Lin . Structural and chemical control in assembly of multicomponent metal-organic coordination networks on a surface . J. Am. Chem. Soc. , 2010 . 132 ( 31 ): 10756 - 10761 . DOI: 10.1021/ja1018578 http://doi.org/10.1021/ja1018578 .

J. Adisoejoso , Y. Li , J. Liu , P. N. Liu , N. Lin . Two-dimensional metallo-supramolecular polymerization:toward size-controlled multi-strand polymers . J. Am. Chem. Soc. , 2012 . 134 ( 45 ): 18526 - 18529 . DOI: 10.1021/ja308480x http://doi.org/10.1021/ja308480x .

H. Walch , J. Dienstmaier , G. Eder , R. Gutzler , S. Schlögl , T. Sirtl , K. Das , M. Schmittel , M. Lackinger . Extended two-dimensional metal-organic frameworks based on thiolate-copper coordination bonds . J. Am. Chem. Soc. , 2011 . 133 ( 20 ): 7909 - 7915 . DOI: 10.1021/ja200661s http://doi.org/10.1021/ja200661s .

U. Schlickum , R. Decker , F. Klappenberger , G. Zoppellaro , S. Klyatskaya , M. Ruben , I. Silanes , A. Arnau , K. Kern , H. Brune , J. V. Barth . Metal-organic honeycomb nanomeshes with tunable cavity size . Nano lett. , 2007 . 7 ( 12 ): 3813 - 3817 . DOI: 10.1021/nl072466m http://doi.org/10.1021/nl072466m .

C. S. Kley , J. Cechal , T. Kumagai , F. Schramm , M. Ruben , S. Stepanow , K. Kern . Highly adaptable two-dimensional metal-organic coordination networks on metal surfaces . J. Am. Chem. Soc. , 2012 . 134 ( 14 ): 6072 - 6075 . DOI: 10.1021/ja211749b http://doi.org/10.1021/ja211749b .

S. Lei , K. Tahara , F. C. de Schryver , M. van der Auweraer , Y. Tobe , S. de Feyter . One building block, two different supramolecular surface-confined patterns:concentration in control at the solid-liquid interface . Angew. Chem. Int. Ed. , 2008 . 47 ( 16 ): 2964 - 2968 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

S. Furukawa , H. Uji-i , K. Tahara , T. Ichikawa , M. Sonoda , F. C. de Schryver , Y. Tobe , S. De Feyter . Molecular geometry directed kagomé and honeycomb networks:toward two-dimensional crystal engineering . J. Am. Chem. Soc. , 2006 . 128 ( 11 ): 3502 - 3503 . DOI: 10.1021/ja0583362 http://doi.org/10.1021/ja0583362 .

S. Berner , M. de Wild , L. Ramoino , S. Ivan , A. Baratoff , H. J. Güntherodt , H. Suzuki , D. Schlettwein , T. A. Jung . Adsorption and two-dimensional phases of a large polar molecule:sub-phthalocyanine on Ag (111) . Phys. Rev. B , 2003 . 68 ( 11 ): 115410 DOI: 10.1103/PhysRevB.68.115410 http://doi.org/10.1103/PhysRevB.68.115410 .

C. S. Kley . Highly adaptable two-dimensional metal-organic coordination networks on metal surfaces . J. Am. Chem. Soc. , 2012 . 134 6072 - 6075 . DOI: 10.1021/ja211749b http://doi.org/10.1021/ja211749b .

N. A. A. Zwaneveld , R. Pawlak , M. Abel , D. Catalin , D. Gigmes , D. Bertin , L. Porte . Organized formation of 2D extended covalent organic frameworks at surfaces . J. Am. Chem. Soc. , 2008 . 130 ( 21 ): 6678 - 6679 . DOI: 10.1021/ja800906f http://doi.org/10.1021/ja800906f .

J. F. Dienstmaier , D. D. Medina , M. Dogru , P. Knochel , T. Bein , W. M. Heckl , M. Lackinger . Isoreticular two-dimensional covalent organic frameworks synthesized by on-surface condensation of diboronic acids . ACS Nano , 2012 . 6 ( 8 ): 7234 - 7242 . DOI: 10.1021/nn302363d http://doi.org/10.1021/nn302363d .

L. Lafferentz . Controlling on-surface polymerization by hierarchical and substrate-directed growth . Nat. Chem. , 2012 . 4 215 - 220 . DOI: 10.1038/nchem.1242 http://doi.org/10.1038/nchem.1242 .

M. Bieri , M. Treier , J. Cai , K. Ait-Mansour , P. Ruffieux , O. Groning , P. Groning , M. Kastler , R. Rieger , X. Feng , K. Mullen , R. Fasel . Porous graphenes:two-dimensional polymer synthesis with atomic precision . Chem. Commun. , 2009 . 45 6919 - 6921 . https://boris.unibe.ch/30940/ https://boris.unibe.ch/30940/ , .

M. O. Blunt , J. C. Russell , N. R. Champness , P. H. Beton . Templating molecular adsorption using a covalent organic framework . Chem. Commun. , 2010 . 46 ( 38 ): 7157 - 7159 . DOI: 10.1039/c0cc01810d http://doi.org/10.1039/c0cc01810d .

M. Bieri , M. T. Nguyen , O. Gröning , J. Cai , M. Treier , K. Aït-Mansour , P. Ruffieux , C. A. Pignedoli , D. Passerone , M. Kastler , K. Müllen , R. Fasel . Two-dimensional polymer formation on surfaces:insight into the roles of precursor mobility and reactivity . J. Am. Chem. Soc. , 2010 . 132 ( 46 ): 16669 - 16676 . DOI: 10.1021/ja107947z http://doi.org/10.1021/ja107947z .

R. Gutzler , H. Walch , G. Eder , S. Kloft , W. M. Heckl , M. Lackinger . Surface mediated synthesis of 2D covalent organic frameworks:1, 3, 5-tris(4-bromophenyl)benzene on graphite(001), Cu(111), and Ag(110) . Chem. Commun. , 2009 . 29 4456 - 4458 . https://www.ncbi.nlm.nih.gov/pubmed/19597624 https://www.ncbi.nlm.nih.gov/pubmed/19597624 , .

L. Cardenas , R. Gutzler , J. Lipton-Duffin , C. Fu , J. L. Brusso , L. E. Dinca , M. Vondracek , Y. Fagot-Revurat , D. Malterre , F. Rosei , D. F. Perepichka . Synthesis and electronic structure of a two dimensional[small pi]-conjugated polythiophene . Chem. Sci. , 2013 . 4 ( 8 ): 3263 - 3268 . DOI: 10.1039/c3sc50800e http://doi.org/10.1039/c3sc50800e .

S. Weigelt , C. Busse , C. Bombis , M. M. Knudsen , K. V. Gothelf , T. Strunskus , C. Wöll , M. Dahlbom , B. Hammer , E. Lægsgaard , F. Besenbacher , T. R. Linderoth . Covalent interlinking of an aldehyde and an amine on a Au(111) surface in ultrahigh vacuum . Angew. Chem. Int. Ed. , 2007 . 46 ( 48 ): 9227 - 9230 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

S. Weigelt , C. Busse , C. Bombis , M. M. Knudsen , K. V. Gothelf , E. Lægsgaard , F. Besenbacher , T. R. Linderoth . Surface synthesis of 2D branched polymer nanostructures . Angew. Chem. Int. Ed. , 2008 . 47 ( 23 ): 4406 - 4410 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

A. C. Marele , R. Mas-Balleste , L. Terracciano , J. Rodriguez-Fernandez , I. Berlanga , S. S. Alexandre , R. Otero , J. M. Gallego , F. Zamora , J. M. Gomez-Rodriguez . Formation of a surface covalent organic framework based on polyester condensation . Chem. Commun. , 2012 . 48 ( 54 ): 6779 - 6781 . DOI: 10.1039/c2cc32270f http://doi.org/10.1039/c2cc32270f .

C. H. Schmitz , J. Ikonomov , M. Sokolowski . Two-dimensional polyamide networks with a broad pore size distribution on the Ag(111) surface . J. Phys. Chem. C , 2011 . 115 ( 15 ): 7270 - 7278 . DOI: 10.1021/jp111723k http://doi.org/10.1021/jp111723k .

M. Treier , N. V. Richardson , R. Fasel . Fabrication of surface-supported low-dimensional polyimide networks . J. Am. Chem. Soc. , 2008 . 130 ( 43 ): 14054 - 14055 . DOI: 10.1021/ja805342n http://doi.org/10.1021/ja805342n .

M. Treier , R. Fasel , N. R. Champness , S. Argent , N. V. Richardson . Molecular imaging of polyimide formation . Phys. Chem. Chem. Phys. , 2009 . 11 ( 8 ): 1209 - 1214 . DOI: 10.1039/b815544p http://doi.org/10.1039/b815544p .

Y. Q. Zhang , N. Kepčija , M. Kleinschrodt , K. Diller , S. Fischer , A. C. Papageorgiou , F. Allegretti , J. Björk , S. Klyatskaya , F. Klappenberger , M. Ruben , J. V. Barth . Homo-coupling of terminal alkynes on a noble metal surface . Nat. Commun. , 2012 . 3 DOI: 10.1038/ncomms2291 http://doi.org/10.1038/ncomms2291 .

H. Y. Gao , H. Wagner , D. Zhong , J. H. Franke , A. Studer , H. Fuchs . Glaser coupling at metal surfaces . Angew. Chem. Int. Ed. , 2013 . 52 ( 14 ): 4024 - 4028 . DOI: 10.1002/anie.v52.14 http://doi.org/10.1002/anie.v52.14 .

J. Eichhorn , W. M. Heckl , M. Lackinger . On-surface polymerization of 1, 4-diethynylbenzene on Cu(111) . Chem. Commun. , 2013 . 49 ( 28 ): 2900 - 2902 . DOI: 10.1039/c3cc40444g http://doi.org/10.1039/c3cc40444g .

Arado O. Díaz , H. Mönig , H. Wagner , J. H. Franke , G. Langewisch , P. A. Held , A. Studer , H. Fuchs . On-surface azide-alkyne cycloaddition on Au(111) . ACS Nano , 2013 . 7 ( 10 ): 8509 - 8515 . DOI: 10.1021/nn4022789 http://doi.org/10.1021/nn4022789 .

S. Schlogl , T. Sirtl , J. Eichhorn , W. M. Heckl , M. Lackinger . Synthesis of two-dimensional phenylene-boroxine networks through in vacuo condensation and on-surface radical addition . Chem. Commun. , 2011 . 47 ( 45 ): 12355 - 12357 . DOI: 10.1039/c1cc13896k http://doi.org/10.1039/c1cc13896k .

A. P. Côté , A. I. Benin , N. W. Ockwig , M. Keeffe , A. J. Matzger , O.M. Yaghi . Porous, crystalline, covalent organic frameworks . Science , 2005 . 310 ( 5751 ): 1166 DOI: 10.1126/science.1120411 http://doi.org/10.1126/science.1120411 .

S. Y. Ding , W. Wang . Covalent organic frameworks (COFs):from design to applications . Chem. Soc. Rev. , 2013 . 42 ( 2 ): 548 - 568 . DOI: 10.1039/C2CS35072F http://doi.org/10.1039/C2CS35072F .

X. Feng , X. Ding , D. Jiang . Covalent organic frameworks . Chem. Soc. Rev. , 2012 . 41 ( 18 ): 6010 - 6022 . DOI: 10.1039/c2cs35157a http://doi.org/10.1039/c2cs35157a .

Y. Jin , Y. Hu , W. Zhang . Tessellated multiporous two-dimensional covalent organic frameworks . Nat. Rev. Chem. , 2017 . 1 DOI: 10.1038/s41570-017-0056 http://doi.org/10.1038/s41570-017-0056 .

D. N. Bunck , W. R. Dichtel . Bulk synthesis of exfoliated two-dimensional polymers using hydrazone-linked covalent organic frameworks . J. Am. Chem. Soc. , 2013 . 135 14952 - 14955 . DOI: 10.1021/ja408243n http://doi.org/10.1021/ja408243n .

I. Berlanga , R. Mas-Ballesté , F. Zamora . Tuning delamination of layered covalent organic frameworks through structural design . Chem. Commun. , 2012 . 48 7976 - 7978 . DOI: 10.1039/c2cc32187d http://doi.org/10.1039/c2cc32187d .

S. Chandra , S. Kandambeth , B. P. Biswal , B. Lukose , S. M. Kunjir , M. Chaudhary , R. Babarao , T. Heine , R. Banerjee . Chemically stable multilayered covalent organic nanosheets from covalent organic frameworks via mechanical delamination . J. Am. Chem. Soc. , 2013 . 135 ( 47 ): 17853 - 17861 . DOI: 10.1021/ja408121p http://doi.org/10.1021/ja408121p .

S. Yang , S. Bruller , Z. S. Wu , Z. Liu , K. Parvez , R. Dong , F. Richard , P. Samori , X. Feng , K. Mullen . Organic radical-assisted electrochemical exfoliation for the scalable production of high-quality graphene . J. Am. Chem. Soc. , 2015 . 137 ( 43 ): 13927 - 13932 . DOI: 10.1021/jacs.5b09000 http://doi.org/10.1021/jacs.5b09000 .

Z. Zeng , Z. Yin , X. Huang , H. Li , Q. He , G. Lu , F. Boey , H. Zhang . Single-layer semiconducting nanosheets:high-yield preparation and device fabrication . Angew. Chem. Int. Ed. , 2011 . 50 ( 47 ): 11093 - 7 . DOI: 10.1002/anie.v50.47 http://doi.org/10.1002/anie.v50.47 .

I. Berlanga , M. L. Ruiz-González , J. M. González-Calbet , J. L. G. Fierro , R. Mas-Ballesté , F. Zamora . Delamination of layered covalent organic frameworks . Small , 2011 . 7 1207 - 1211 . DOI: 10.1002/smll.v7.9 http://doi.org/10.1002/smll.v7.9 .

J. W. Colson , J. A. Mann , C. R. DeBlase , W. R. Dichtel . Patterned growth of oriented 2D covalent organic framework thin films on single-layer graphene . J. Polym. Sci., Part A:Polym. Chem. , 2015 . 53 ( 2 ): 378 - 384 . DOI: 10.1002/pola.27399 http://doi.org/10.1002/pola.27399 .

J. W. Colson , A. R. Woll , A. Mukherjee , M. P. Levendorf , E. L. Spitler , V. B. Shields , M. G. Spencer , J. Park , W. R. Dichtel . Oriented 2D covalent organic framework thin films on single-layer graphene . Science , 2011 . 332 ( 6026 ): 228 - 231 . DOI: 10.1126/science.1202747 http://doi.org/10.1126/science.1202747 .

R. Tanoue , R. Higuchi , N. Enoki , Y. Miyasato , S. Uemura , N. Kimizuka , A. Z. Stieg , J. K. Gimzewski , M. Kunitake . Thermodynamically controlled self-assembly of covalent nanoarchitectures in aqueous solution . ACS Nano , 2011 . 5 ( 5 ): 3923 - 3929 . DOI: 10.1021/nn200393q http://doi.org/10.1021/nn200393q .

L. Xu , X. Zhou , Y. Yu , W. Q. Tian , J. Ma , S. Lei . Surface-confined crystalline two-dimensional covalent organic frameworks via on-surface Schiff-base coupling . ACS Nano , 2013 . 7 ( 9 ): 8066 - 8073 . DOI: 10.1021/nn403328h http://doi.org/10.1021/nn403328h .

L. Xu , X. Zhou , W. Q. Tian , T. Gao , Y. F. Zhang , S. Lei , Z. F. Liu . Surface-confined single-layer covalent organic framework on single-layer graphene grown on copper foil . Angew. Chem. Int. Ed. , 2014 . 53 ( 36 ): 9564 - 9568 . DOI: 10.1002/anie.201400273 http://doi.org/10.1002/anie.201400273 .

J. Y. Yue , X. H. Liu , B. Sun , D. Wang . The on-surface synthesis of imine-based covalent organic frameworks with non-aromatic linkage . Chem. Commun. , 2015 . 51 ( 76 ): 14318 - 14321 . DOI: 10.1039/C5CC05689F http://doi.org/10.1039/C5CC05689F .

C. Z. Guan , D. Wang , L. J. Wan . Construction and repair of highly ordered 2D covalent networks by chemical equilibrium regulation . Chem. Commun. , 2012 . 48 2943 - 2945 . DOI: 10.1039/c2cc16892h http://doi.org/10.1039/c2cc16892h .

X. H. Liu , C. Z. Guan , S. Y. Ding , W. Wang , H. J. Yan , D. Wang , L. J. Wan . On-surface synthesis of single-layered two-dimensional covalent organic frameworks via solid-vapor interface reactions . J. Am. Chem. Soc. , 2013 . 135 ( 28 ): 10470 - 10474 . DOI: 10.1021/ja403464h http://doi.org/10.1021/ja403464h .

G. X. Li , Y. L. Li , H. B. Liu , Y. B. Guo , Y. J. Li , D. B. Zhu . Architecture of graphdiyne nanoscale films . Chem. Commun. , 2010 . 46 ( 19 ): 3256 - 3258 . DOI: 10.1039/b922733d http://doi.org/10.1039/b922733d .

S. Wang , L. Yi , J. E. Halpert , X. Lai , Y. Liu , H. Cao , R. Yu , D. Wang , Y. Li . A novel and highly efficient photocatalyst based on P25-graphdiyne nanocomposite . Small , 2012 . 8 ( 2 ): 265 - 271 . https://www.researchgate.net/publication/51834201_A_Novel_and_Highly_Efficient_Photocatalyst_Based_on_P25-Graphdiyne_Nanocomposite https://www.researchgate.net/publication/51834201_A_Novel_and_Highly_Efficient_Photocatalyst_Based_on_P25-Graphdiyne_Nanocomposite , .

N. Yang , Y. Liu , H. Wen , Z. Tang , H. Zhao , Y. Li , D. Wang . Photocatalytic properties of graphdiyne and graphene modified TiO 2 :from theory to experiment . ACS Nano , 2013 . 7 ( 2 ): 1504 - 1512 . DOI: 10.1021/nn305288z http://doi.org/10.1021/nn305288z .

H. Du , Z. Deng , Z. Lü , Y. Yin , L. Yu , H. Wu , Z. Chen , Y. Zou , Y. Wang , H. Liu , Y. Li . The effect of graphdiyne doping on the performance of polymer solar cells . Synth. Met. , 2011 . 161 ( 19-20 ): 2055 - 2057 . DOI: 10.1016/j.synthmet.2011.04.015 http://doi.org/10.1016/j.synthmet.2011.04.015 .

S. L. Zhang , H. P. Du , J. J. He , C. S. Huang , H. B. Liu , G. L. Cui , Y. L. Li . Nitrogen-doped graphdiyne applied for lithium-ion storage . ACS Appl. Mater. Interfaces , 2016 . 8 ( 13 ): 8467 - 8473 . DOI: 10.1021/acsami.6b00255 http://doi.org/10.1021/acsami.6b00255 .

H. Yang , S. L. Zhang , L. H. Han , Z. Zhang , Z. Xue , J. Gao , Y. J. Li , C. S. Huang , Y. P. Yi , H. B. Liu , Y. L. Li . High conductive two-dimensional covalent organic framework for lithium storage with large capacity . ACS Appl. Mater. Interfaces , 2016 . 8 ( 8 ): 5366 - 5375 . DOI: 10.1021/acsami.5b12370 http://doi.org/10.1021/acsami.5b12370 .

H. P. Du , H. Yang , C. S. Huang , J. J. He , H. B. Liu , Y. L. Li . Graphdiyne applied for lithium-ion capacitors displaying high power and energy densities . Nano Energy , 2016 . 22 615 - 622 . DOI: 10.1016/j.nanoen.2016.02.052 http://doi.org/10.1016/j.nanoen.2016.02.052 .

S. L. Zhang , H. B. Liu , C. S. Huang , G. L. Cui , Y. L. Li . Bulk graphdiyne powder applied for highly efficient lithium storage . Chem. Commun. , 2015 . 51 ( 10 ): 1834 - 1837 . DOI: 10.1039/C4CC08706B http://doi.org/10.1039/C4CC08706B .

C. S. Huang , S. L. Zhang , H. B. Liu , Y. J. Li , G. T. Cui , Y. L. Li . Graphdiyne for high capacity and long-life lithium storage . Nano Energy , 2015 . 11 481 - 489 . DOI: 10.1016/j.nanoen.2014.11.036 http://doi.org/10.1016/j.nanoen.2014.11.036 .

T. Bauer , Z. Zheng , A. Renn , R. Enning , A. Stemmer , J. Sakamoto , A. D. Schlüter . Synthesis of free-standing, monolayered organometallic sheets at the air/water interface . Angew. Chem. Int. Ed. , 2011 . 50 ( 34 ): 7879 - 7884 . DOI: 10.1002/anie.v50.34 http://doi.org/10.1002/anie.v50.34 .

Z. Zheng , C. S. Ruiz-Vargas , T. Bauer , A. Rossi , P. Payamyar , A. Schütz , A. Stemmer , J. Sakamoto , A. D. Schlüter . Square-micrometer-sized, free-standing organometallic sheets and their square-centimeter-sized multilayers on solid substrates . Macromol. Rapid. Commun. , 2013 . 34 ( 21 ): 1670 - 1680 . DOI: 10.1002/marc.v34.21 http://doi.org/10.1002/marc.v34.21 .

Z. Zheng , L. Opilik , F. Schiffmann , W. Liu , G. Bergamini , P. Ceroni , L. T. Lee , A. Schütz , J. Sakamoto , R. Zenobi , J. VandeVondele , A. D. Schlüter . Synthesis of two-dimensional analogues of copolymers by site-to-site transmetalation of organometallic monolayer sheets . J. Am. Chem. Soc. , 2014 . 136 ( 16 ): 6103 - 6110 . DOI: 10.1021/ja501849y http://doi.org/10.1021/ja501849y .

T. Kambe , R. Sakamoto , K. Hoshiko , K. Takada , M. Miyachi , J. H. Ryu , S. Sasaki , J. Kim , K. Nakazato , M. Takata , H. Nishihara . π -Conjugated nickel bis(dithiolene) complex nanosheet . J. Am. Chem. Soc. , 2013 . 135 ( 7 ): 2462 - 2465 . DOI: 10.1021/ja312380b http://doi.org/10.1021/ja312380b .

T. Kambe , R. Sakamoto , T. Kusamoto , T. Pal , N. Fukui , K. Hoshiko , T. Shimojima , Z. Wang , T. Hirahara , K. Ishizaka , S. Hasegawa , F. Liu , H. Nishihara . Redox control and high conductivity of nickel bis(dithiolene) complex π -nanosheet:a potential organic two-dimensional topological insulator . J. Am. Chem. Soc. , 2014 . 136 ( 41 ): 14357 - 14360 . DOI: 10.1021/ja507619d http://doi.org/10.1021/ja507619d .

R. Dong , M. Pfeffermann , H. Liang , Z. Zheng , X. Zhu , J. Zhang , X. Feng . Large-area, free-standing, two-dimensional supramolecular polymer single-layer sheets for highly efficient electrocatalytic hydrogen evolution . Angew. Chem. Int. Ed. , 2015 . 54 ( 41 ): 12058 - 12063 . DOI: 10.1002/anie.201506048 http://doi.org/10.1002/anie.201506048 .

R. Sakamoto , K. Hoshiko , Q. Liu , T. Yagi , T. Nagayama , S. Kusaka , M. Tsuchiya , Y. Kitagawa , W. Wong , H. Nishihara . A photofunctional bottom-up bis(dipyrrinato)zinc(Ⅱ) complex nanosheet . Nat. Commun. , 2015 . 6 DOI: 10.1038/ncomms7713 http://doi.org/10.1038/ncomms7713 .

S. Motoyama , R. Makiura , O. Sakata , H. Kitagawa . Highly crystalline nanofilm by layering of porphyrin metal-organic framework sheets . J. Am. Chem. Soc. , 2011 . 133 ( 15 ): 5640 - 5643 . DOI: 10.1021/ja110720f http://doi.org/10.1021/ja110720f .

Y. Chen , M. Li , P. Payamyar , Z. Zheng , J. Sakamoto , A. D. Schlüter . Room temperature synthesis of a covalent monolayer sheet at air/water interface using a shape-persistent photoreactive amphiphilic monomer . ACS Macro Lett. , 2014 . 3 ( 2 ): 153 - 158 . DOI: 10.1021/mz400597k http://doi.org/10.1021/mz400597k .

P. Payamyar , K. Kaja , C. Ruiz-Vargas , A. Stemmer , D. J. Murray , C. J. Johnson , B. T. King , F. Schiffmann , J. VandeVondele , A. Renn , S. Götzinger , P. Ceroni , A. Schütz , L. T. Lee , Z. Zheng , J. Sakamoto , A. D. Schlüter . Synthesis of a covalent monolayer sheet by photochemical anthracene dimerization at the air/water interface and its mechanical characterization by AFM indentation . Adv. Mater. , 2014 . 26 ( 13 ): 2052 - 2058 . DOI: 10.1002/adma.201304705 http://doi.org/10.1002/adma.201304705 .

D. J. Murray , D. D. Patterson , P. Payamyar , R. Bhola , W. Song , M. Lackinger , A. D. Schlüter , B. T. King . Large area synthesis of a nanoporous two-dimensional polymer at the air/water interface . J. Am. Chem. Soc. , 2015 . 137 ( 10 ): 3450 - 3453 . DOI: 10.1021/ja512018j http://doi.org/10.1021/ja512018j .

W. Dai , F. Shao , J. Szczerbiński , R. McCaffrey , R. Zenobi , Y. Jin , A. D. Schlüter , W. Zhang . Synthesis of a two-dimensional covalent organic monolayer through dynamic imine chemistry at the air/water interface . Angew. Chem. Int. Ed. , 2016 . 55 ( 1 ): 213 - 217 . DOI: 10.1002/anie.201508473 http://doi.org/10.1002/anie.201508473 .

H. Sahabudeen , H. Y. Qi , B. A. Glatz , D. Tranca , R. H. Dong , Y. Hou , T. Zhang , C. Kuttner , T. Lehnert , G. Seifert , U. Kaiser , A. Fery , Z. K. Zheng , X. L. Feng . Wafer-sized multifunctional polyimine-based two-dimensional conjugated polymers with high mechanical stiffness . Nat. Commun. , 2016 . DOI: 10.1038/ncomms13461 http://doi.org/10.1038/ncomms13461 .

R. Matsuoka , R. Sakamoto , K. Hoshiko , S. Sasaki , H. Masunaga , K. Nagashio , H. Nishihara . Crystalline graphdiyne nanosheets produced at a gas/liquid or liquid/liquid interface . J. Am. Chem. Soc. , 2017 . 139 ( 8 ): 3145 - 3152 . DOI: 10.1021/jacs.6b12776 http://doi.org/10.1021/jacs.6b12776 .

R. Makiura , S. Motoyama , Y. Umemura , H. Yamanaka , O. Sakata , H. Kitagawa . Surface nano-architecture of a metal0organic framework . Nat. Mater. , 2010 . 9 ( 7 ): 565 - 571 . DOI: 10.1038/nmat2769 http://doi.org/10.1038/nmat2769 .

T. Rodenas , I. Luz , G. Prieto , B. Seoane , H. Miro , A. Corma , F. Kapteijn , F. X. Llabres i Xamena , J. Gascon . Metal-organic framework nanosheets in polymer composite materials for gas separation . Nat. Mater. , 2015 . 14 ( 1 ): 48 - 55 . DOI: 10.1038/nmat4113 http://doi.org/10.1038/nmat4113 .

M. Hu , S. Ishihara , Y. Yamauchi . Bottom-up synthesis of monodispersed single-crystalline cyano-bridged coordination polymer nanoflakes . Angew. Chem. Int. Ed. , 2013 . 52 ( 4 ): 1235 - 1239 . DOI: 10.1002/anie.201208501 http://doi.org/10.1002/anie.201208501 .

N. L. Netzer , F. R. Dai , Z. Wang , C. Jiang . pH-Modulated molecular assemblies and surface properties of metal-organic supercontainers at the air-water interface . Angew. Chem. Int. Ed. , 2014 . 53 ( 41 ): 10965 - 10969 . DOI: 10.1002/anie.201406733 http://doi.org/10.1002/anie.201406733 .

G. Xu , T. Yamada , K. Otsubo , S. Sakaida , H. Kitagawa . Facile "modular assembly" for fast construction of a highly oriented crystalline MOF nanofilm . J. Am. Chem. Soc. , 2012 . 134 ( 40 ): 16524 - 16527 . DOI: 10.1021/ja307953m http://doi.org/10.1021/ja307953m .

R. Makiura , O. Konovalov . Interfacial growth of large-area single-layer metal-organic framework nanosheets . Sci. Rep. , 2013 . 3 DOI: 10.1038/srep02506 http://doi.org/10.1038/srep02506 .

M. Pfeffermann , R. Dong , R. Graf , W. Zajaczkowski , T. Gorelik , W. Pisula , A. Narita , K. Mullen , X. Feng . Free-standing monolayer two-dimensional supramolecular organic framework with good internal order . J. Am. Chem. Soc. , 2015 . 137 ( 45 ): 14525 - 14532 . DOI: 10.1021/jacs.5b09638 http://doi.org/10.1021/jacs.5b09638 .

M. J. Kory , M. Bergeler , M. Reiher , A. D. Schlüter . Facile synthesis and theoretical conformation analysis of a triazine-based double-decker rotor molecule with three anthracene blades . Chem. Eur. J. , 2014 . 20 6934 - 6938 . DOI: 10.1002/chem.201400364 http://doi.org/10.1002/chem.201400364 .

P. Kissel , R. Erni , W. B. Schweizer , M. D. Rossell , B. T. King , T. Bauer , S. Götzinger , A. D. Schlüter , J. Sakamoto . A two-dimensional polymer prepared by organic synthesis . Nat. Chem. , 2012 . 4 ( 4 ): 287 - 291 . DOI: 10.1038/nchem.1265 http://doi.org/10.1038/nchem.1265 .

M. J. Kory , M. Worle , T. Weber , P. Payamyar , S. W. van de Poll , J. Dshemuchadse , N. Trapp , A. D. Schluter . Gram-scale synthesis of two-dimensional polymer crystals and their structure analysis by X-ray diffraction . Nat. Chem. , 2014 . 6 ( 9 ): 779 - 784 . DOI: 10.1038/nchem.2007 http://doi.org/10.1038/nchem.2007 .

P. Kissel , D. J. Murray , W. J. Wulftange , V. J. Catalano , B. T. King . A nanoporous two-dimensional polymer by single-crystal-to-single-crystal photopolymerization . Nat. Chem. , 2014 . 6 ( 9 ): 774 - 778 . DOI: 10.1038/nchem.2008 http://doi.org/10.1038/nchem.2008 .

R. Bhola , P. Payamyar , D. J. Murray , B. Kumar , A. J. Teator , M. U. Schmidt , S. M. Hammer , A. Saha , J. Sakamoto , A. D. Schluter , B. T. King . A two-dimensional polymer from the anthracene dimer and triptycene motifs . J. Am. Chem. Soc. , 2013 . 135 ( 38 ): 14134 - 14141 . DOI: 10.1021/ja404351p http://doi.org/10.1021/ja404351p .

R. Z. Lange , G. Hofer , T. Weber , A. D. Schlüter . A two-dimensional polymer synthesized through topochemical[2 + 2]-cycloaddition on the multigram scale . J. Am. Chem. Soc. , 2017 . 139 ( 5 ): 2053 - 2059 . DOI: 10.1021/jacs.6b11857 http://doi.org/10.1021/jacs.6b11857 .

K. D. Zhang , J. Tian , D. Hanifi , Y. Zhang , A. C. H. Sue , T. Y. Zhou , L. Zhang , X. Zhao , Y. Liu , Z. T. Li . Toward a single-layer two-dimensional honeycomb supramolecular organic framework in water . J. Am. Chem. Soc. , 2013 . 135 ( 47 ): 17913 - 17918 . DOI: 10.1021/ja4086935 http://doi.org/10.1021/ja4086935 .

L. Y. Cao , Z. K. Lin , F. Peng , W. W. Wang , R. Y. Huang , C. Wang , J. W. Yan , J. Liang , Z. M. Zhang , T. Zhang , L. S. Long , J. L. Sun , W. B. Lin . Self-supporting metal-organic layers as single-site solid catalysts . Angew. Chem. Int. Ed. , 2016 . 55 ( 16 ): 4962 - 4966 . DOI: 10.1002/anie.v55.16 http://doi.org/10.1002/anie.v55.16 .

K. Baek , G. Yun , Y. Kim , D. Kim , R. Hota , I. Hwang , D. Xu , Y. H. Ko , G. H. Gu , J. H. Suh , C. G. Park , B. J. Sung , K. Kim . Free-standing, single-monomer-thick two-dimensional polymers through covalent self-assembly in aolution . J. Am. Chem. Soc. , 2013 . 135 ( 17 ): 6523 - 6528 . DOI: 10.1021/ja4002019 http://doi.org/10.1021/ja4002019 .

T. Y. Zhou , F. Lin , Z. T. Li , X. Zhao . Single-step solution-phase synthesis of free-standing two-dimensional polymers and their evolution into hollow spheres . Macromolecules , 2013 . 46 ( 19 ): 7745 - 7752 . DOI: 10.1021/ma401570g http://doi.org/10.1021/ma401570g .

J. Kim , K. Baek , D. Shetty , N. Selvapalam , G. Yun , N. H. Kim , Y. H. Ko , K. M. Park , I. Hwang , K. Kim . Reversible morphological transformation between polymer nanocapsules and thin films through dynamic covalent self-assembly . Angew. Chem. Int. Ed. , 2015 . 127 ( 9 ): 2731 - 2735 . DOI: 10.1002/ange.201411842 http://doi.org/10.1002/ange.201411842 .

M. Calik , T. Sick , M. Dogru , M. Döblinger , S. Datz , H. Budde , A. Hartschuh , F. Auras , T. Bein . From highly crystalline to outer surface-functionalized covalent organic frameworks-a modulation approach . J. Am. Chem. Soc. , 2015 . 138 ( 4 ): 1234 - 1239 . http://pubs.acs.org/doi/full/10.1021/jacs.5b10708?src=recsys http://pubs.acs.org/doi/full/10.1021/jacs.5b10708?src=recsys , .

Y. Zhao , R. H. M. Bernitzky , M. J. Kory , G. Hofer , J. Hofkens , A. D. Schlüter . Decorating the edges of a 2D polymer with a fluorescence label . J. Am. Chem. Soc. , 2016 . 138 ( 28 ): 8976 - 8981 . DOI: 10.1021/jacs.6b05456 http://doi.org/10.1021/jacs.6b05456 .

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