Dynamic covalent synthesis of aryleneethynylene cages through alkyne metathesis: dimer, tetramer, or interlocked complex?

Wang, Qi; Yu, Chao; Zhang, Chenxi; Long, Hai; Azarnoush, Setareh; Jin, Yinghua; Zhang, Wei

doi:10.1039/c5sc04977f

Title: Dynamic covalent synthesis of aryleneethynylene cages through alkyne metathesis: dimer, tetramer, or interlocked complex?

Journal Article · Fri Feb 12 00:00:00 EST 2016 · Chemical Science

DOI:https://doi.org/10.1039/c5sc04977f· OSTI ID:1254927

^[1];

^[1]; Zhang, Chenxi ^[1]; Long, Hai ^[2]; Azarnoush, Setareh ^[1]; Jin, Yinghua ^[1]; Zhang, Wei ^[1]

Univ. of Colorado, Boulder, CO (United States)
National Renewable Energy Lab. (NREL), Golden, CO (United States)

A dynamic covalent approach towards rigid aryleneethynylene covalent organic polyhedrons (COPs) was explored. Our study on the relationship of the COP structures and the geometry of their building blocks reveals that the topology of aryleneethynylene COPs strongly depends on the size of the building blocks. A tetramer (D_2h symmetric), dimer, or interlocked complex can be formed from monomers with the same face-to-edge angle but in different sizes. As alkyne metathesis is a self-exchange reaction and non-directional, the cyclooligomerization of multi-alkyne monomers involves both intramolecular cyclization and intermolecular metathesis reaction, resulting in complicated thermodynamic process disturbed by kinetic competition. Although a tetrahedron-shaped tetramer (T_d symmetric) has comparable thermodynamic stability to a D_2h symmetric tetramer, its formation is kinetically disfavored and was not observed experimentally. Aryleneethynylene COPs consist of purely unsaturated carbon backbones and exhibit large internal cavities, which would have interesting applications in host–guest chemistry and development of porous materials.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1254927

Report Number(s):: NREL-JA-2C00-66530; MainId:18143; UUID:7fd051fe-ae22-e611-97db-d89d67132a6d; MainAdminID:6621

Journal Information:: Chemical Science, Vol. 7, Issue 5; Related Information: Chemical Science; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 74 works

Citation information provided by
Web of Science

References (69)

Highly Active Multidentate Alkyne Metathesis Catalysts: Ligand-Activity Relationship and Their Applications in Efficient Synthesis of Porphyrin-Based Aryleneethynylene Polymers Jyothish, Kuthanapillil; Wang, Qi; Zhang, Wei Advanced Synthesis & Catalysis, Vol. 354, Issue 11-12 https://doi.org/10.1002/adsc.201200243	journal	July 2012
Building on architectural principles for three-dimensional metallosupramolecular construction Smulders, Maarten M. J.; Riddell, Imogen A.; Browne, Colm Chem. Soc. Rev., Vol. 42, Issue 4 https://doi.org/10.1039/C2CS35254K	journal	January 2013
Recent Advances in the Syntheses and Applications of Molybdenum and Tungsten Alkylidene and Alkylidyne Catalysts for the Metathesis of Alkenes and Alkynes Schrock, Richard R.; Czekelius, Constantin Advanced Synthesis & Catalysis, Vol. 349, Issue 1-2 https://doi.org/10.1002/adsc.200600459	journal	January 2007
Shape-Persistent Arylene Ethynylene Organic Hosts for Fullerenes Yu, Chao; Jin, Yinghua; Zhang, Wei The Chemical Record, Vol. 15, Issue 1 https://doi.org/10.1002/tcr.201402076	journal	December 2014
Coordination Assemblies from a Pd(II)-Cornered Square Complex Fujita, Makoto; Tominaga, Masahide; Hori, Akiko Accounts of Chemical Research, Vol. 38, Issue 4 https://doi.org/10.1021/ar040153h	journal	April 2005
Discovery of an Organic Trefoil Knot Ponnuswamy, N.; Cougnon, F. B. L.; Clough, J. M. Science, Vol. 338, Issue 6108 https://doi.org/10.1126/science.1227032	journal	November 2012
Disulfide exchange: exposing supramolecular reactivity through dynamic covalent chemistry Black, Samuel P.; Sanders, Jeremy K. M.; Stefankiewicz, Artur R. Chem. Soc. Rev., Vol. 43, Issue 6 https://doi.org/10.1039/C3CS60326A	journal	January 2014
Template-directed synthesis employing reversible imine bond formation Meyer, Cari D.; Joiner, C. Steven; Stoddart, J. Fraser Chemical Society Reviews, Vol. 36, Issue 11 https://doi.org/10.1039/b513441m	journal	January 2007
A Highly C ₇₀ Selective Shape-Persistent Rectangular Prism Constructed through One-Step Alkyne Metathesis Zhang, Chenxi; Wang, Qi; Long, Hai Journal of the American Chemical Society, Vol. 133, Issue 51 https://doi.org/10.1021/ja210418t	journal	December 2011
Exploring the Formation Pathways of Donor−Acceptor Catenanes in Aqueous Dynamic Combinatorial Libraries Cougnon, Fabien B. L.; Au-Yeung, Ho Yu; Pantoş, G. Dan Journal of the American Chemical Society, Vol. 133, Issue 9 https://doi.org/10.1021/ja111407m	journal	March 2011
From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry Lehn, Jean-Marie Chem. Soc. Rev., Vol. 36, Issue 2 https://doi.org/10.1039/B616752G	journal	January 2007
Boronic acids as building blocks for molecular nanostructures and polymeric materials Severin, Kay Dalton Transactions, Issue 27 https://doi.org/10.1039/b902849h	journal	January 2009
Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne Metathesis Zhang, Wei; Moore, Jeffrey S. Journal of the American Chemical Society, Vol. 126, Issue 40 https://doi.org/10.1021/ja046531v	journal	October 2004
Development and testing of a general amber force field Wang, Junmei; Wolf, Romain M.; Caldwell, James W. Journal of Computational Chemistry, Vol. 25, Issue 9 https://doi.org/10.1002/jcc.20035	journal	January 2004
Molecular Borromean Rings Chichak, K. S. Science, Vol. 304, Issue 5675 https://doi.org/10.1126/science.1096914	journal	May 2004
Dynamic Combinatorial Chemistry Corbett, Peter T.; Leclaire, Julien; Vial, Laurent Chemical Reviews, Vol. 106, Issue 9 https://doi.org/10.1021/cr020452p	journal	September 2006
Dynamic Covalent Chemistry Rowan, Stuart J.; Cantrill, Stuart J.; Cousins, Graham R. L. Angewandte Chemie International Edition, Vol. 41, Issue 6, p. 898-952 https://doi.org/10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E	journal	March 2002
A Tetrameric Cage with D _{2 h} Symmetry through Alkyne Metathesis Wang, Qi; Zhang, Chenxi; Noll, Bruce C. Angewandte Chemie International Edition, Vol. 53, Issue 40 https://doi.org/10.1002/anie.201404880	journal	August 2014
Selective Molecular Recognition, C−H Bond Activation, and Catalysis in Nanoscale Reaction Vessels Fiedler, Dorothea; Leung, Dennis H.; Bergman, Robert G. Accounts of Chemical Research, Vol. 38, Issue 4 https://doi.org/10.1021/ar040152p	journal	April 2005
Linking rings without templates Beves, Jonathan E.; Leigh, David A. Nature Chemistry, Vol. 2, Issue 9 https://doi.org/10.1038/nchem.745	journal	July 2010
Dynamic imine chemistry Belowich, Matthew E.; Stoddart, J. Fraser Chemical Society Reviews, Vol. 41, Issue 6 https://doi.org/10.1039/c2cs15305j	journal	January 2012
Porous organic cages Tozawa, Tomokazu; Jones, James T. A.; Swamy, Shashikala I. Nature Materials, Vol. 8, Issue 12, p. 973-978 https://doi.org/10.1038/nmat2545	journal	October 2009
Porous organic molecular materials Tian, Jian; Thallapally, Praveen K.; McGrail, B. Peter CrystEngComm, Vol. 14, Issue 6 https://doi.org/10.1039/c2ce06457j	journal	January 2012
Synthesis and Structure of A Triptycene-Based Nanosized Molecular Cage Zhang, Chun; Chen, Chuan-Feng The Journal of Organic Chemistry, Vol. 72, Issue 24 https://doi.org/10.1021/jo7017526	journal	November 2007
Adsorption-Driven Self-Sorting of Dynamic Imine Libraries Hsu, Chia-Wei; Miljanić, Ognjen Š. Angewandte Chemie International Edition, Vol. 54, Issue 7 https://doi.org/10.1002/anie.201409741	journal	December 2014
Structural Characterization of a Cyclohexamericmeta-Phenyleneethynylene Made by Alkyne Metathesis with In Situ Catalysts Ge, Ping-Hua; Fu, Wei; Herrmann, Wolfgang A. Angewandte Chemie, Vol. 39, Issue 20 https://doi.org/10.1002/1521-3773(20001016)39:20<3607::AID-ANIE3607>3.0.CO;2-S	journal	October 2000
Alkyne Metathesis on the Rise Fürstner, Alois Angewandte Chemie International Edition, Vol. 52, Issue 10 https://doi.org/10.1002/anie.201204513	journal	January 2013
Reaction Pathways Leading to Arylene Ethynylene Macrocycles via Alkyne Metathesis Zhang, Wei; Moore, Jeffrey S. Journal of the American Chemical Society, Vol. 127, Issue 33 https://doi.org/10.1021/ja053466w	journal	August 2005
A Molecular Solomon Link Pentecost, Cari D.; Chichak, Kelly S.; Peters, Andrea J. Angewandte Chemie International Edition, Vol. 46, Issue 1-2 https://doi.org/10.1002/anie.200603521	journal	January 2007
Complete Regioselective Addition of Grignard Reagents to Pyrazine N -Oxides, Toward an Efficient Enantioselective Synthesis of Substituted Piperazines Andersson, Hans; Banchelin, Thomas Sainte-Luce; Das, Sajal Organic Letters, Vol. 12, Issue 2 https://doi.org/10.1021/ol902619h	journal	January 2010
Continuous flow synthesis of a carbon-based molecular cage macrocycle via a three-fold homocoupling reaction Kitchin, Melanie; Konstas, Kristina; Sumby, Christopher J. Chemical Communications, Vol. 51, Issue 75 https://doi.org/10.1039/C5CC05181A	journal	January 2015
Shape-Persistent Molecular Architectures of Nanoscale Dimension Moore, Jeffrey S. Accounts of Chemical Research, Vol. 30, Issue 10 https://doi.org/10.1021/ar950232g	journal	October 1997
Polyimine Container Molecules and Nanocapsules Rue, Nicholas M.; Sun, Junling; Warmuth, Ralf Israel Journal of Chemistry, Vol. 51, Issue 7 https://doi.org/10.1002/ijch.201100064	journal	July 2011
Boronic acid building blocks: tools for self assembly Nishiyabu, Ryuhei; Kubo, Yuji; James, Tony D. Chem. Commun., Vol. 47, Issue 4 https://doi.org/10.1039/C0CC02921A	journal	January 2011
Metathesis of alkynes by a molybdenum hexacarbonyl–resorcinol catalyst Mortreux, André; Blanchard, Michel J. Chem. Soc., Chem. Commun., Issue 19 https://doi.org/10.1039/C39740000786	journal	January 1974
Alkyne Metathesis: Catalysts and Synthetic Applications Zhang, Wei; Moore, Jeffrey S. Advanced Synthesis & Catalysis, Vol. 349, Issue 1-2 https://doi.org/10.1002/adsc.200600476	journal	January 2007
Recent advances in dynamic covalent chemistry Jin, Yinghua; Yu, Chao; Denman, Ryan J. Chemical Society Reviews, Vol. 42, Issue 16 https://doi.org/10.1039/c3cs60044k	journal	January 2013
Shape-Persistent Macrocycles: Structures and Synthetic Approaches from Arylene and Ethynylene Building Blocks Zhang, Wei; Moore, Jeffrey S. Angewandte Chemie International Edition, Vol. 45, Issue 27 https://doi.org/10.1002/anie.200503988	journal	July 2006
Multidentate Triphenolsilane-Based Alkyne Metathesis Catalysts Yang, Haishen; Liu, Zhenning; Zhang, Wei Advanced Synthesis & Catalysis, Vol. 355, Issue 5 https://doi.org/10.1002/adsc.201201105	journal	March 2013
Solution-Phase Dynamic Assembly of Permanently Interlocked Aryleneethynylene Cages through Alkyne Metathesis Wang, Qi; Yu, Chao; Long, Hai Angewandte Chemie International Edition, Vol. 54, Issue 26 https://doi.org/10.1002/anie.201501679	journal	May 2015
Dynamic combinatorial libraries: new opportunities in systems chemistry Hunt, Rosemary A. R.; Otto, Sijbren Chem. Commun., Vol. 47, Issue 3 https://doi.org/10.1039/C0CC03759A	journal	January 2011
Template synthesis of molecular knots Ayme, Jean-François; Beves, Jonathon E.; Campbell, Christopher J. Chem. Soc. Rev., Vol. 42, Issue 4 https://doi.org/10.1039/C2CS35229J	journal	January 2013
Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles Chakrabarty, Rajesh; Mukherjee, Partha Sarathi; Stang, Peter J. Chemical Reviews, Vol. 111, Issue 11, p. 6810-6918 https://doi.org/10.1021/cr200077m	journal	November 2011
Recent advances in the development of alkyne metathesis catalysts Wu, Xian; Tamm, Matthias Beilstein Journal of Organic Chemistry, Vol. 7 https://doi.org/10.3762/bjoc.7.12	journal	January 2011
Functional Molecular Flasks: New Properties and Reactions within Discrete, Self-Assembled Hosts Yoshizawa, Michito; Klosterman, Jeremy K.; Fujita, Makoto Angewandte Chemie International Edition, Vol. 48, Issue 19, p. 3418-3438 https://doi.org/10.1002/anie.200805340	journal	April 2009
Templated Dynamic Synthesis of a [3]Catenane Cougnon, Fabien B. L.; Jenkins, Nicholas A.; Pantoş, G. Dan Angewandte Chemie International Edition, Vol. 51, Issue 6 https://doi.org/10.1002/anie.201106885	journal	December 2011
Towards Highly Active and Robust Alkyne Metathesis Catalysts: Recent Developments in Catalyst Design Jyothish, Kuthanapillil; Zhang, Wei Angewandte Chemie International Edition, Vol. 50, Issue 37 https://doi.org/10.1002/anie.201102678	journal	July 2011
Dynamic Covalent Chemistry Approaches Toward Macrocycles, Molecular Cages, and Polymers Jin, Yinghua; Wang, Qi; Taynton, Philip Accounts of Chemical Research, Vol. 47, Issue 5 https://doi.org/10.1021/ar500037v	journal	April 2014
Development of organic porous materials through Schiff-base chemistry Jin, Yinghua; Zhu, Youlong; Zhang, Wei CrystEngComm, Vol. 15, Issue 8 https://doi.org/10.1039/C2CE26394G	journal	January 2013
Kinetically Controlled Porosity in a Robust Organic Cage Material Avellaneda, Antonio; Valente, Peter; Burgun, Alexandre Angewandte Chemie International Edition, Vol. 52, Issue 13 https://doi.org/10.1002/anie.201209922	journal	February 2013
Shape-Persistent Organic Cage Compounds by Dynamic Covalent Bond Formation Mastalerz, Michael Angewandte Chemie International Edition, Vol. 49, Issue 30 https://doi.org/10.1002/anie.201000443	journal	June 2010
High-Symmetry Coordination Cages via Self-Assembly Seidel, S. Russell; Stang, Peter J. Accounts of Chemical Research, Vol. 35, Issue 11 https://doi.org/10.1021/ar010142d	journal	November 2002
Introducing A Podand Motif to Alkyne Metathesis Catalyst Design: A Highly Active Multidentate Molybdenum(VI) Catalyst that Resists Alkyne Polymerization Jyothish, Kuthanapillil; Zhang, Wei Angewandte Chemie International Edition, Vol. 50, Issue 15 https://doi.org/10.1002/anie.201007559	journal	March 2011
A Molecular Solomon Link Pentecost, Cari D.; Chichak, Kelly S.; Peters, Andrea J. Angewandte Chemie, Vol. 119, Issue 1-2 https://doi.org/10.1002/ange.200603521	journal	January 2007
Shape-Persistent Macrocycles: Structures and Synthetic Approaches from Arylene and Ethynylene Building Blocks Zhang, Wei; Moore, Jeffrey S. ChemInform, Vol. 37, Issue 41 https://doi.org/10.1002/chin.200641239	journal	October 2006
From Supramolecular Chemistry Towards Constitutional Dynamic Chemistry and Adaptive Chemistry Lehn, Jean-Marie ChemInform, Vol. 38, Issue 20 https://doi.org/10.1002/chin.200720232	journal	May 2007
Dynamic Covalent Chemistry Rowan, Stuart J.; Cantrill, Stuart J.; Cousins, Graham R. L. Angewandte Chemie International Edition, Vol. 41, Issue 9 https://doi.org/10.1002/1521-3773(20020503)41:9<1460::aid-anie11111460>3.0.co;2-n	journal	May 2002
Introducing A Podand Motif to Alkyne Metathesis Catalyst Design: A Highly Active Multidentate Molybdenum(VI) Catalyst that Resists Alkyne Polymerization Jyothish, Kuthanapillil; Zhang, Wei Angewandte Chemie, Vol. 123, Issue 15 https://doi.org/10.1002/ange.201007559	journal	March 2011
Kinetically Controlled Porosity in a Robust Organic Cage Material Avellaneda, Antonio; Valente, Peter; Burgun, Alexandre Angewandte Chemie, Vol. 125, Issue 13 https://doi.org/10.1002/ange.201209922	journal	February 2013
A Tetrameric Cage with D _{2 h} Symmetry through Alkyne Metathesis Wang, Qi; Zhang, Chenxi; Noll, Bruce C. Angewandte Chemie, Vol. 126, Issue 40 https://doi.org/10.1002/ange.201404880	journal	August 2014
Adsorption-Driven Self-Sorting of Dynamic Imine Libraries Hsu, Chia-Wei; Miljanić, Ognjen Š. Angewandte Chemie, Vol. 127, Issue 7 https://doi.org/10.1002/ange.201409741	journal	December 2014
Solution‐Phase Dynamic Assembly of Permanently Interlocked Aryleneethynylene Cages through Alkyne Metathesis Wang, Qi; Yu, Chao; Long, Hai Angewandte Chemie, Vol. 127, Issue 26 https://doi.org/10.1002/ange.201501679	journal	May 2015
High-Symmetry Coordination Cages via Self-Assembly Seidel, S. Russell; Stang, Peter J. ChemInform, Vol. 34, Issue 5 https://doi.org/10.1002/chin.200305277	journal	February 2003
NADPH levels affect cellular epigenetic state by inhibiting HDAC3–Ncor complex Li, Wei; Kou, Junjie; Qin, Junying Nature Metabolism, Vol. 3, Issue 1 https://doi.org/10.1038/s42255-020-00330-2	journal	January 2021
Templated Dynamic Synthesis of a [3]Catenane Cougnon, Fabien B. L.; Jenkins, Nicholas A.; Pantoş, G. Dan Angewandte Chemie, Vol. 124, Issue 6 https://doi.org/10.1002/ange.201106885	journal	December 2011
Recent Advances in the Syntheses and Applications of Molybdenum and Tungsten Alkylidene and Alkylidyne Catalysts for the Metathesis of Alkenes and Alkynes Schrock, Richard R.; Czekelius, Constantin ChemInform, Vol. 38, Issue 19 https://doi.org/10.1002/chin.200719219	journal	May 2007
Structural Characterization of a Cyclohexamericmeta-Phenyleneethynylene Made by Alkyne Metathesis with In Situ Catalysts Ge, Ping-Hua; Fu, Wei; Herrmann, Wolfgang A. Angewandte Chemie, Vol. 112, Issue 20 https://doi.org/10.1002/1521-3757(20001016)112:20<3753::aid-ange3753>3.0.co;2-b	journal	October 2000
Dynamic Combinatorial Chemistry Corbett, Peter T.; Leclaire, Julien; Vial, Laurent ChemInform, Vol. 37, Issue 48 https://doi.org/10.1002/chin.200648268	journal	November 2006
A Molecular Solomon Link. Pentecost, Cari D.; Chichak, Kelly S.; Peters, Andrea J. ChemInform, Vol. 38, Issue 9 https://doi.org/10.1002/chin.200709060	journal	February 2007

Cited By (28)

Networked Cages for Enhanced CO ₂ Capture and Sensing Wang, Zhen; Ma, Hui; Zhai, Tian-Long Advanced Science, Vol. 5, Issue 7 https://doi.org/10.1002/advs.201800141	journal	May 2018
A Three-Dimensionally π-Conjugated Diradical Molecular Cage Gu, Xiao; Gopalakrishna, Tullimilli Y.; Phan, Hoa Angewandte Chemie, Vol. 129, Issue 48 https://doi.org/10.1002/ange.201709537	journal	October 2017
Formation of a Macrocycles-in-a-Macrocycle Superstructure with All- gauche Conformation by Reversible Radical Association Yuan, Liu; Han, Yi; Tao, Tao Angewandte Chemie, Vol. 130, Issue 29 https://doi.org/10.1002/ange.201804720	journal	June 2018
Alkyne Metathesis with Silica-Supported and Molecular Catalysts at Parts-per-Million Loadings Estes, Deven P.; Bittner, Celine; Àrias, Òscar Angewandte Chemie International Edition, Vol. 55, Issue 45 https://doi.org/10.1002/anie.201605129	journal	August 2016
Trapping White Phosphorus within a Purely Organic Molecular Container Produced by Imine Condensation Jiao, Tianyu; Chen, Liang; Yang, Dong Angewandte Chemie International Edition, Vol. 56, Issue 46 https://doi.org/10.1002/anie.201708246	journal	October 2017
Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds Beuerle, Florian; Gole, Bappaditya Angewandte Chemie International Edition, Vol. 57, Issue 18 https://doi.org/10.1002/anie.201710190	journal	March 2018
Formation of a Macrocycles-in-a-Macrocycle Superstructure with All- gauche Conformation by Reversible Radical Association Yuan, Liu; Han, Yi; Tao, Tao Angewandte Chemie International Edition, Vol. 57, Issue 29 https://doi.org/10.1002/anie.201804720	journal	June 2018
Dynamic Behavior of Covalent Organic Cages Ono, Kosuke; Iwasawa, Nobuharu Chemistry – A European Journal, Vol. 24, Issue 68 https://doi.org/10.1002/chem.201802253	journal	October 2018
Unraveling the Mechanism of 1,3-Diyne Cross-Metathesis Catalyzed by Silanolate-Supported Tungsten Alkylidyne Complexes Schnabel, Tobias M.; Melcher, Daniel; Brandhorst, Kai Chemistry - A European Journal, Vol. 24, Issue 36 https://doi.org/10.1002/chem.201802561	journal	June 2018
Nonconjugated Hydrocarbons as Rigid‐Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry Locke, Gemma M.; Bernhard, Stefan S. R.; Senge, Mathias O. Chemistry – A European Journal, Vol. 25, Issue 18 https://doi.org/10.1002/chem.201804225	journal	January 2019
Well‐Defined Alkyne Metathesis Catalysts: Developments and Recent Applications Ehrhorn, Henrike; Tamm, Matthias Chemistry – A European Journal https://doi.org/10.1002/chem.201804511	journal	December 2018
Poly(aryleneethynylene)s: Properties, Applications and Synthesis Through Alkyne Metathesis Ortiz, Michael; Yu, Chao; Jin, Yinghua Topics in Current Chemistry, Vol. 375, Issue 4 https://doi.org/10.1007/s41061-017-0156-1	journal	June 2017
Porous organic cages: soluble, modular and molecular pores Hasell, Tom; Cooper, Andrew I. Nature Reviews Materials, Vol. 1, Issue 9 https://doi.org/10.1038/natrevmats.2016.53	journal	July 2016
Dynamic self-correcting nucleophilic aromatic substitution Ong, Wen Jie; Swager, Timothy M. Nature Chemistry, Vol. 10, Issue 10 https://doi.org/10.1038/s41557-018-0122-8	journal	September 2018
Endohedrally functionalised porous organic cages Burgun, Alexandre; Valente, Peter; Evans, Jack D. Chemical Communications, Vol. 52, Issue 57 https://doi.org/10.1039/c6cc04423a	journal	January 2016
Formation of paramagnetic metallacyclobutadienes by reaction of diaminoacetylenes with molybdenum alkylidyne complexes Àrias, Òscar; Brandhorst, Kai; Baabe, Dirk Dalton Transactions, Vol. 46, Issue 14 https://doi.org/10.1039/c7dt00305f	journal	January 2017
Flexibility of components alters the self-assembly pathway of Pd ₂ L ₄ coordination cages Kai, Shumpei; Maddala, Sai Prakash; Kojima, Tatsuo Dalton Transactions, Vol. 47, Issue 10 https://doi.org/10.1039/c8dt00112j	journal	January 2018
A facile solution-phase synthetic approach for constructing phenol-based porous organic cages and covalent organic frameworks Zhang, Lei; Liang, Rongran; Hang, Cheng Green Chemistry, Vol. 22, Issue 8 https://doi.org/10.1039/c9gc04033a	journal	January 2020
Computational discovery of a large-imine-cage-based porous molecular material and its application in water desalination Bernabei, Marco; Pérez Soto, Raul; Gómez García, Ismael Molecular Systems Design & Engineering, Vol. 4, Issue 4 https://doi.org/10.1039/c9me00018f	journal	January 2019
A convenient one-pot nanosynthesis of a C(sp ² )–C(sp ³ )-linked 3D grid via an ‘A ₂ + B ₃ ’ approach Wei, Ying; Luo, Mengcheng; Zhang, Guangwei Organic & Biomolecular Chemistry, Vol. 17, Issue 27 https://doi.org/10.1039/c9ob00754g	journal	January 2019
A tetrahedral molecular cage with a responsive vertex Pattillo, Christopher C.; Moore, Jeffrey S. Chemical Science, Vol. 10, Issue 29 https://doi.org/10.1039/c9sc02047k	journal	January 2019
Modulation of hydrophilicity inside the cavity of molecular rectangles self-assembled under ambient conditions Khullar, Sadhika; Mandal, Sanjay K. Chemical Communications, Vol. 56, Issue 57 https://doi.org/10.1039/d0cc02379e	journal	January 2020
Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes Bittner, Celine; Bockfeld, Dirk; Tamm, Matthias Beilstein Journal of Organic Chemistry, Vol. 15 https://doi.org/10.3762/bjoc.15.246	journal	January 2019
Alkyne Metathesis with Silica-Supported and Molecular Catalysts at Parts-per-Million Loadings Estes, Deven P.; Bittner, Celine; Àrias, Òscar Angewandte Chemie, Vol. 128, Issue 45 https://doi.org/10.1002/ange.201605129	journal	August 2016
A Three-Dimensionally π-Conjugated Diradical Molecular Cage Gu, Xiao; Gopalakrishna, Tullimilli Y.; Phan, Hoa Angewandte Chemie International Edition, Vol. 56, Issue 48 https://doi.org/10.1002/anie.201709537	journal	October 2017
Trapping White Phosphorus within a Purely Organic Molecular Container Produced by Imine Condensation Jiao, Tianyu; Chen, Liang; Yang, Dong Angewandte Chemie, Vol. 129, Issue 46 https://doi.org/10.1002/ange.201708246	journal	October 2017
Unraveling the Mechanism of 1,3-Diyne Cross-Metathesis Catalyzed by Silanolate-Supported Tungsten Alkylidyne Complexes Schnabel, Tobias M.; Melcher, Daniel; Brandhorst, Kai Chemistry - A European Journal, Vol. 24, Issue 36 https://doi.org/10.1002/chem.201801651	journal	June 2018
Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex Ehrhorn, Henrike; Schlösser, Janin; Bockfeld, Dirk Beilstein Journal of Organic Chemistry, Vol. 14 https://doi.org/10.3762/bjoc.14.220	journal	September 2018

Similar Records

Solution-Phase Dynamic Assembly of Permanently Interlocked Aryleneethynylene Cages through Alkyne Metathesis

Journal Article · Fri May 08 00:00:00 EDT 2015 · Angewandte Chemie · OSTI ID:1254927

Wang, Qi; Yu, Chao; Long, Hai; +3 more

Solution‐Phase Dynamic Assembly of Permanently Interlocked Aryleneethynylene Cages through Alkyne Metathesis

Journal Article · Fri May 08 00:00:00 EDT 2015 · Angewandte Chemie · OSTI ID:1254927

Wang, Qi; Yu, Chao; Long, Hai; +3 more

Poly(aryleneethynylene)s: Properties, Applications and Synthesis Through Alkyne Metathesis

Journal Article · Mon Jun 26 00:00:00 EDT 2017 · Topics in Current Chemistry · OSTI ID:1254927

Ortiz, Michael; Yu, Chao; Jin, Yinghua; +1 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
aryleneethynylene
cage
alkyne
metathesis
dynamic assembly

Title: Dynamic covalent synthesis of aryleneethynylene cages through alkyne metathesis: dimer, tetramer, or interlocked complex?

Citation Formats

References (69)

Cited By (28)

Similar Records

Related Subjects