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

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

Journal Article · 20 June 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.

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

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

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1408449

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

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 59 works

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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
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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 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 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 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 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 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 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 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 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 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 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
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 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