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Modular and predictable assembly of porous organic molecular crystals

Modular and predictable assembly of porous organic molecular crystals
Modular and predictable assembly of porous organic molecular crystals
Nanoporous molecular frameworks are important in applications such as separation, storage and catalysis. Empirical rules exist for their assembly but it is still challenging to place and segregate functionality in three-dimensional porous solids in a predictable way. Indeed, recent studies of mixed crystalline frameworks suggest a preference for the statistical distribution of functionalities throughout the pores rather than, for example, the functional group localization found in the reactive sites of enzymes. This is a potential limitation for 'one-pot' chemical syntheses of porous frameworks from simple starting materials. An alternative strategy is to prepare porous solids from synthetically preorganized molecular pores. In principle, functional organic pore modules could be covalently prefabricated and then assembled to produce materials with specific properties. However, this vision of mix-and-match assembly is far from being realized, not least because of the challenge in reliably predicting three-dimensional structures for molecular crystals, which lack the strong directional bonding found in networks. Here we show that highly porous crystalline solids can be produced by mixing different organic cage modules that self-assemble by means of chiral recognition. The structures of the resulting materials can be predicted computationally, allowing in silico materials design strategies. The constituent pore modules are synthesized in high yields on gram scales in a one-step reaction. Assembly of the porous co-crystals is as simple as combining the modules in solution and removing the solvent. In some cases, the chiral recognition between modules can be exploited to produce porous organic nanoparticles. We show that the method is valid for four different cage modules and can in principle be generalized in a computationally predictable manner based on a lock-and-key assembly between modules.
0028-0836
367-371
Jones, James T.A.
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Hasell, Tom
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Wu, Xiaofeng
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Bacsa, John
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Jelfs, Kim E
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Schmidtmann, Marc
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Chong, Samantha Y.
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Adams, Dave J.
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Trewin, Abbie
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Schiffman, Florian
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Cora, Furio
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Slater, Ben
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Steiner, Alexander
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Day, Graeme M.
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Cooper, Andrew I
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Jones, James T.A.
bda2c4c2-7673-4efd-8a88-02d036f2b8db
Hasell, Tom
6c8f5286-f4e2-456e-a3cd-dcfd3d164e52
Wu, Xiaofeng
9814fd49-9cef-4279-8b71-cfbdf2634123
Bacsa, John
8877bf1f-d692-4526-b61e-ee3f3c053204
Jelfs, Kim E
81483f1c-e77f-447d-affe-a29b590cac7b
Schmidtmann, Marc
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Chong, Samantha Y.
2e23eea0-c8eb-48bb-8e69-7f3a50d0e812
Adams, Dave J.
d95e4f11-7580-43cb-802d-ad8ac0161c8a
Trewin, Abbie
b3c7ad9a-f460-48cd-b532-1a44d69f4854
Schiffman, Florian
e552c32c-40da-4a18-8526-03daf0d68c04
Cora, Furio
08ac2594-ab17-4436-8807-29f0bcc69f8f
Slater, Ben
d9494ea4-0916-47e1-8127-da6eae488c86
Steiner, Alexander
90c4fb4a-d977-448d-91c6-e38338d4e4d2
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Cooper, Andrew I
8cad6e52-32d3-487b-98e3-3f01cec43553

Jones, James T.A., Hasell, Tom, Wu, Xiaofeng, Bacsa, John, Jelfs, Kim E, Schmidtmann, Marc, Chong, Samantha Y., Adams, Dave J., Trewin, Abbie, Schiffman, Florian, Cora, Furio, Slater, Ben, Steiner, Alexander, Day, Graeme M. and Cooper, Andrew I (2011) Modular and predictable assembly of porous organic molecular crystals. Nature, 474 (7351), 367-371. (doi:10.1038/nature10125). (PMID:21677756)

Record type: Article

Abstract

Nanoporous molecular frameworks are important in applications such as separation, storage and catalysis. Empirical rules exist for their assembly but it is still challenging to place and segregate functionality in three-dimensional porous solids in a predictable way. Indeed, recent studies of mixed crystalline frameworks suggest a preference for the statistical distribution of functionalities throughout the pores rather than, for example, the functional group localization found in the reactive sites of enzymes. This is a potential limitation for 'one-pot' chemical syntheses of porous frameworks from simple starting materials. An alternative strategy is to prepare porous solids from synthetically preorganized molecular pores. In principle, functional organic pore modules could be covalently prefabricated and then assembled to produce materials with specific properties. However, this vision of mix-and-match assembly is far from being realized, not least because of the challenge in reliably predicting three-dimensional structures for molecular crystals, which lack the strong directional bonding found in networks. Here we show that highly porous crystalline solids can be produced by mixing different organic cage modules that self-assemble by means of chiral recognition. The structures of the resulting materials can be predicted computationally, allowing in silico materials design strategies. The constituent pore modules are synthesized in high yields on gram scales in a one-step reaction. Assembly of the porous co-crystals is as simple as combining the modules in solution and removing the solvent. In some cases, the chiral recognition between modules can be exploited to produce porous organic nanoparticles. We show that the method is valid for four different cage modules and can in principle be generalized in a computationally predictable manner based on a lock-and-key assembly between modules.

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Published date: 16 June 2011
Organisations: Chemistry

Identifiers

Local EPrints ID: 340212
URI: http://eprints.soton.ac.uk/id/eprint/340212
ISSN: 0028-0836
PURE UUID: b951f437-7122-4281-9ee7-7e9399e1e717
ORCID for Graeme M. Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 15 Jun 2012 09:11
Last modified: 15 Sep 2021 01:59

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Contributors

Author: James T.A. Jones
Author: Tom Hasell
Author: Xiaofeng Wu
Author: John Bacsa
Author: Kim E Jelfs
Author: Marc Schmidtmann
Author: Samantha Y. Chong
Author: Dave J. Adams
Author: Abbie Trewin
Author: Florian Schiffman
Author: Furio Cora
Author: Ben Slater
Author: Alexander Steiner
Author: Graeme M. Day ORCID iD
Author: Andrew I Cooper

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