Computationally-Guided Synthetic Control over Pore Size in Isostructural Porous Organic Cages

Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles; Little, Marc A.; Holden, Daniel L.; Chen, Linjiang; Chong, Samantha Y.; Alston, Ben M.; Clowes, Rob; Haranczyk, Maciej; Briggs, Michael E.; Hasell, Tom; Day, Graeme M.; Cooper, Andrew I.

doi:10.1021/acscentsci.7b00145

Computationally-Guided Synthetic Control over Pore Size in Isostructural Porous Organic Cages

Journal Article · Tue Jun 20 00:00:00 EDT 2017 · ACS Central Science

DOI:https://doi.org/10.1021/acscentsci.7b00145· OSTI ID:1408449

Slater, Anna G. ^[1]; Reiss, Paul S. ^[1]; Pulido, Angeles ^[2]; Little, Marc A. ^[1]; Holden, Daniel L. ^[1]; Chen, Linjiang ^[1]; ^[1]; Alston, Ben M. ^[1]; Clowes, Rob ^[1]; Haranczyk, Maciej ^[3]; Briggs, Michael E. ^[1]; Hasell, Tom ^[1]; Day, Graeme M. ^[2]; ^[1]

Univ. of Liverpool (United Kingdom). Dept. of Chemistry, Materials Innovation Factory
Univ. of Southampton (United Kingdom). School of Chemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

The physical properties of 3-D porous solids are defined by their molecular geometry. Hence, precise control of pore size, pore shape, and pore connectivity are needed to tailor them for specific applications. However, for porous molecular crystals, the modification of pore size by adding pore-blocking groups can also affect crystal packing in an unpredictable way. This precludes strategies adopted for isoreticular metal-organic frameworks, where addition of a small group, such as a methyl group, does not affect the basic framework topology. Here, we narrow the pore size of a cage molecule, CC3, in a systematic way by introducing methyl groups into the cage windows. Computational crystal structure prediction was used to anticipate the packing preferences of two homochiral methylated cages, CC14-R and CC15-R, and to assess the structure-energy landscape of a CC15-R/CC3-S cocrystal, designed such that both component cages could be directed to pack with a 3-D, interconnected pore structure. The experimental gas sorption properties of these three cage systems agree well with physical properties predicted by computational energy-structure-function maps.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1408449

Journal Information:: ACS Central Science, Journal Name: ACS Central Science Journal Issue: 7 Vol. 3; ISSN 2374-7943

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (48)

Tailoring Microporosity in Covalent Organic Frameworks Tilford, R. William; Mugavero, Sam J.; Pellechia, Perry J. Advanced Materials, Vol. 20, Issue 14 https://doi.org/10.1002/adma.200800030	journal	July 2008
Porous Organic Alloys Hasell, Tom; Chong, Samantha Y.; Schmidtmann, Marc Angewandte Chemie, Vol. 124, Issue 29 https://doi.org/10.1002/ange.201202849	journal	June 2012
Nanoporous Organic Polymer/Cage Composite Membranes Bushell, Alexandra F.; Budd, Peter M.; Attfield, Martin P. Angewandte Chemie, Vol. 125, Issue 4 https://doi.org/10.1002/ange.201206339	journal	December 2012
A Permanent Mesoporous Organic Cage with an Exceptionally High Surface Area Zhang, Gang; Presly, Oliver; White, Fraser Angewandte Chemie, Vol. 126, Issue 6 https://doi.org/10.1002/ange.201308924	journal	January 2014
Conjugated Microporous Poly(aryleneethynylene) Networks Jiang, Jia-Xing; Su, Fabing; Trewin, Abbie Angewandte Chemie International Edition, Vol. 47, Issue 7 https://doi.org/10.1002/anie.200890021	journal	February 2008
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
Porphyrin Boxes: Rationally Designed Porous Organic Cages Hong, Soonsang; Rohman, Md. Rumum; Jia, Jiangtao Angewandte Chemie International Edition, Vol. 54, Issue 45 https://doi.org/10.1002/anie.201505531	journal	August 2015
Predicting Inclusion Behaviour and Framework Structures in Organic Crystals Cruz-Cabeza, AuroraâJ.; Day, GraemeâM.; Jones, William Chemistry - A European Journal, Vol. 15, Issue 47 https://doi.org/10.1002/chem.200901703	journal	December 2009
Periphery-Substituted [4+6] Salicylbisimine Cage Compounds with Exceptionally High Surface Areas: Influence of the Molecular Structure on Nitrogen Sorption Properties Schneider, Markus W.; Oppel, Iris M.; Ott, Holger Chemistry - A European Journal, Vol. 18, Issue 3 https://doi.org/10.1002/chem.201102857	journal	December 2011
Intrinsic D ₂ /H ₂ Selectivity of NaX Zeolite: Interplay between Adsorption and Kinetic Factors Kowalczyk, Piotr; Terzyk, Artur P.; Gauden, Piotr A. The Journal of Physical Chemistry C, Vol. 119, Issue 27 https://doi.org/10.1021/acs.jpcc.5b03913	journal	June 2015
Transition State Theory Methods To Measure Diffusion in Flexible Nanoporous Materials: Application to a Porous Organic Cage Crystal Camp, Jeffrey S.; Sholl, David S. The Journal of Physical Chemistry C, Vol. 120, Issue 2 https://doi.org/10.1021/acs.jpcc.5b11111	journal	January 2016
Synthetic Strategies, Structure Patterns, and Emerging Properties in the Chemistry of Modular Porous Solids^† Yaghi, Omar M.; Li, Hailian; Davis, Charles Accounts of Chemical Research, Vol. 31, Issue 8, p. 474-484 https://doi.org/10.1021/ar970151f	journal	August 1998
Opening the Gate: Framework Flexibility in ZIF-8 Explored by Experiments and Simulations Fairen-Jimenez, D.; Moggach, S. A.; Wharmby, M. T. Journal of the American Chemical Society, Vol. 133, Issue 23 https://doi.org/10.1021/ja202154j	journal	June 2011
Supramolecular Engineering of Intrinsic and Extrinsic Porosity in Covalent Organic Cages Bojdys, Michael J.; Briggs, Michael E.; Jones, James T. A. Journal of the American Chemical Society, Vol. 133, Issue 41 https://doi.org/10.1021/ja2056374	journal	October 2011
Bespoke Force Field for Simulating the Molecular Dynamics of Porous Organic Cages Holden, Daniel; Jelfs, Kim E.; Cooper, Andrew I. The Journal of Physical Chemistry C, Vol. 116, Issue 31 https://doi.org/10.1021/jp305129w	journal	July 2012
Feasibility of Mixed Matrix Membrane Gas Separations Employing Porous Organic Cages Evans, Jack D.; Huang, David M.; Hill, Matthew R. The Journal of Physical Chemistry C, Vol. 118, Issue 3 https://doi.org/10.1021/jp4079184	journal	January 2014
Metal–Organic Frameworks for Removal of Xe and Kr from Nuclear Fuel Reprocessing Plants Liu, Jian; Thallapally, Praveen K.; Strachan, Denis Langmuir, Vol. 28, Issue 31 https://doi.org/10.1021/la301870n	journal	July 2012
Modular and predictable assembly of porous organic molecular crystals Jones, James T. A.; Hasell, Tom; Wu, Xiaofeng Nature, Vol. 474, Issue 7351 https://doi.org/10.1038/nature10125	journal	June 2011
Functional materials discovery using energy–structure–function maps Pulido, Angeles; Chen, Linjiang; Kaczorowski, Tomasz Nature, Vol. 543, Issue 7647 https://doi.org/10.1038/nature21419	journal	March 2017
Porous organic molecular solids by dynamic covalent scrambling Jiang, Shan; Jones, James T. A.; Hasell, Tom Nature Communications, Vol. 2, Issue 1 https://doi.org/10.1038/ncomms1207	journal	February 2011
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
Modelling organic crystal structures using distributed multipole and polarizability-based model intermolecular potentials Price, Sarah L.; Leslie, Maurice; Welch, Gareth W. A. Physical Chemistry Chemical Physics, Vol. 12, Issue 30 https://doi.org/10.1039/c004164e	journal	January 2010
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
Organic cage compounds – from shape-persistency to function Zhang, Gang; Mastalerz, Michael Chem. Soc. Rev., Vol. 43, Issue 6 https://doi.org/10.1039/c3cs60358j	journal	January 2014
Conjugated Microporous Poly(aryleneethynylene) Networks Jiang, Jia-Xing; Su, Fabing; Trewin, Abbie Angewandte Chemie International Edition, Vol. 46, Issue 45 https://doi.org/10.1002/anie.200701595	journal	September 2007
A Salicylbisimine Cage Compound with High Surface Area and Selective CO₂/CH₄ Adsorption Mastalerz, Michael; Schneider, Markus W.; Oppel, Iris M. Angewandte Chemie International Edition, Vol. 50, Issue 5, p. 1046-1051 https://doi.org/10.1002/anie.201005301	journal	November 2010
Porous Organic Alloys Hasell, Tom; Chong, Samantha Y.; Schmidtmann, Marc Angewandte Chemie International Edition, Vol. 51, Issue 29 https://doi.org/10.1002/anie.201202849	journal	June 2012
Nanoporous Organic Polymer/Cage Composite Membranes Bushell, Alexandra F.; Budd, Peter M.; Attfield, Martin P. Angewandte Chemie International Edition, Vol. 52, Issue 4 https://doi.org/10.1002/anie.201206339	journal	December 2012
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
A Permanent Mesoporous Organic Cage with an Exceptionally High Surface Area Zhang, Gang; Presly, Oliver; White, Fraser Angewandte Chemie International Edition, Vol. 53, Issue 6 https://doi.org/10.1002/anie.201308924	journal	January 2014
Effect of Functionalized Groups on Gas-Adsorption Properties: Syntheses of Functionalized Microporous Metal-Organic Frameworks and Their High Gas-Storage Capacity Wang, Yanlong; Tan, Chunhong; Sun, Zhihao Chemistry - A European Journal, Vol. 20, Issue 5 https://doi.org/10.1002/chem.201302541	journal	December 2013
Quantum Sieving for Separation of Hydrogen Isotopes Using MOFs: Quantum Sieving for Separation of Hydrogen Isotopes Using MOFs Oh, Hyunchul; Hirscher, Michael European Journal of Inorganic Chemistry, Vol. 2016, Issue 27 https://doi.org/10.1002/ejic.201600253	journal	June 2016
Porous Organic Cages for Gas Chromatography Separations Kewley, Adam; Stephenson, Andrew; Chen, Linjiang Chemistry of Materials, Vol. 27, Issue 9 https://doi.org/10.1021/acs.chemmater.5b01112	journal	April 2015
Dynamic Quantum Molecular Sieving Separation of D ₂ from H ₂ –D ₂ Mixture with Nanoporous Materials Niimura, Subaru; Fujimori, Toshihiko; Minami, Daiki Journal of the American Chemical Society, Vol. 134, Issue 45 https://doi.org/10.1021/ja305809u	journal	November 2012
Controlling the Crystallization of Porous Organic Cages: Molecular Analogs of Isoreticular Frameworks Using Shape-Specific Directing Solvents Hasell, Tom; Culshaw, Jamie L.; Chong, Samantha Y. Journal of the American Chemical Society, Vol. 136, Issue 4 https://doi.org/10.1021/ja409594s	journal	January 2014
Porous Organic Cages for Sulfur Hexafluoride Separation Hasell, Tom; Miklitz, Marcin; Stephenson, Andrew Journal of the American Chemical Society, Vol. 138, Issue 5 https://doi.org/10.1021/jacs.5b11797	journal	January 2016
Molecular shape sorting using molecular organic cages Mitra, Tamoghna; Jelfs, Kim E.; Schmidtmann, Marc Nature Chemistry, Vol. 5, Issue 4 https://doi.org/10.1038/nchem.1550	journal	January 2013
Separation of rare gases and chiral molecules by selective binding in porous organic cages Chen, Linjiang; Reiss, Paul S.; Chong, Samantha Y. Nature Materials, Vol. 13, Issue 10 https://doi.org/10.1038/nmat4035	journal	July 2014
Organic cage compounds – from shape-persistency to function Zhang, Gang; Mastalerz, Michael Chem. Soc. Rev., Vol. 43, Issue 6 https://doi.org/10.1039/C3CS60358J	journal	January 2014
Porous coordination polymers based on functionalized Schiff base linkers: enhanced CO ₂ uptake by pore surface modification Bhattacharya, Biswajit; Haldar, Ritesh; Dey, Rajdip Dalton Trans., Vol. 43, Issue 5 https://doi.org/10.1039/C3DT52266K	journal	January 2014
Guest control of structure in porous organic cages Little, Marc A.; Chong, Samantha Y.; Schmidtmann, Marc Chem. Commun., Vol. 50, Issue 67 https://doi.org/10.1039/C4CC04158E	journal	January 2014
Dynamic flow synthesis of porous organic cages Briggs, Michael E.; Slater, Anna G.; Lunt, Neil Chemical Communications, Vol. 51, Issue 98 https://doi.org/10.1039/C5CC07447A	journal	January 2015
Understanding static, dynamic and cooperative porosity in molecular materials Holden, Daniel; Chong, Samantha Y.; Chen, Linjiang Chemical Science, Vol. 7, Issue 8 https://doi.org/10.1039/C6SC00713A	journal	January 2016
Quantum sieving: feasibility and challenges for the separation of hydrogen isotopes in nanoporous materials Cai, Jinjun; Xing, Yanlong; Zhao, Xuebo RSC Advances, Vol. 2, Issue 23 https://doi.org/10.1039/c2ra01284g	journal	January 2012
Predicted crystal energy landscapes of porous organic cages Pyzer-Knapp, Edward O.; Thompson, Hugh P. G.; Schiffmann, Florian Chem. Sci., Vol. 5, Issue 6 https://doi.org/10.1039/c4sc00095a	journal	January 2014
Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage Eddaoudi, Mohamed; Kim, Jaheon; Rosi, Nathaniel Science, Vol. 295, Issue 5554, p. 469-472 https://doi.org/10.1126/science.1067208	journal	January 2002
Porous, Crystalline, Covalent Organic Frameworks Côté, Adrien P.; Benin, Annabelle I.; Ockwig, Nathan W. Science, Vol. 310, Issue 5751, p. 1166-1170 https://doi.org/10.1126/science.1120411	journal	November 2005
Function-led design of new porous materials Slater, A. G.; Cooper, A. I. Science, Vol. 348, Issue 6238 https://doi.org/10.1126/science.aaa8075	journal	May 2015

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CCDC 1533778: Experimental Crystal Structure Determination: SENNOR : 5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane solvate Slater, Anna; Reiss, Paul; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0qw The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533779: Experimental Crystal Structure Determination: SENNUX : 4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene Slater, Anna; Reiss, Paul; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0rx The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533780: Experimental Crystal Structure Determination: SENPAF : 4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene monohydrate Slater, Anna; Reiss, Paul; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0sy The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533781: Experimental Crystal Structure Determination: SENPIN : 4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane solvate Space Group: C 2 2 21 (20), Cell: a 17.0198(15)Å b 22.755(2)Å c 22.4114(19)Å, α 90° β 90° γ 90° Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0tz The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533782: Experimental Crystal Structure Determination: SENPOT : 4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane diethyl ether solvate Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0v0 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533783: Experimental Crystal Structure Determination: SENPUZ : 4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene methanol dichloromethane solvate Space Group: P 3 (143), Cell: a 26.1841(11)Å b 26.1841(11)Å c 11.1858(5)Å, α 90° β 90° γ 120° Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0w1 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533784: Experimental Crystal Structure Determination: SENQAG : 4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane solvate Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0x2 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533785: Experimental Crystal Structure Determination: SENQEK : 4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dinitrogen clathrate Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0y3 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533786: Experimental Crystal Structure Determination: SENQIO : ,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane solvate hemihydrate Space Group: P 1 (2), Cell: a 14.0638(8)Å b 16.2235(9)Å c 21.9305(13)Å, α 92.6404(17)° β 106.7014(16)° γ 113.7812(16)° Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh0z4 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533787: Experimental Crystal Structure Determination: SENQOU : R-4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,8,12,14(84),15,17,19,23,27,29(83),30,32,34,38,42,44(72),45,47,49,53,57,59,61,65,69,73,77,81-triacontaene S-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dodecahydrate Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh106 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533788: Experimental Crystal Structure Determination: SENQUA : R-4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane n-hexane solvate Slater, Anna G.; Reiss, Paul S.; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh117 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533789: Experimental Crystal Structure Determination: SENRAH : (rac)-4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane solvate monohydrate Slater, Anna; Reiss, Paul; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh128 The current record is supplemented by this dataset	dataset	February 2017
CCDC 1533790: Experimental Crystal Structure Determination: SENREL : (R)-4,13,19,28,34,43,49,58,61,70,73,82-dodecamethyl-5,12,20,27,35,42,50,57,62,69,74,81-dodecaazatridecacyclo[29.29.10.1016,46.13,59.114,18.129,33.144,48.06,11.021,26.036,41.051,56.063,68.075,80]tetraoctaconta-1,3(71),4,12,14(84),15,17,19,27,29(83),30,32,34,42,44(72),45,47,49,57,59,61,69,73,81-tetracosaene dichloromethane diethyl ether solvate Slater, Anna; Reiss, Paul; Pulido, Angeles https://doi.org/10.5517/ccdc.csd.cc1nh139 The current record is supplemented by this dataset	dataset	February 2017

Computationally-Guided Synthetic Control over Pore Size in Isostructural Porous Organic Cages

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