title: Periphery-Functionalized Porous Organic Cages.
abstract: By synthesizing derivatives of a trans-1,2-diaminocyclohexane precursor, three new functionalized porous organic cages were prepared with different chemical functionalities on the cage periphery. The introduction of twelve methyl groups (CC16) resulted in frustration of the cage packing mode, which more than doubled the surface area compared to the parent cage, CC3. The analogous installation of twelve hydroxyl groups provided an imine cage (CC17) that combines permanent porosity with the potential for post-synthetic modification of the cage exterior. Finally, the incorporation of bulky dihydroethanoanthracene groups was found to direct self-assembly towards the formation of a larger [8+12] cage, rather than the expected [4+6], cage molecule (CC18). However, CC18 was found to be non-porous, most likely due to cage collapse upon desolvation.
authors.affiliation: Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
authors.forename: Paul S
authors.initials: PS
authors.lastname: Reiss
authors.affiliation: Department of Chemistry and Materials Innovation Factory, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.
authors.forename: Marc A
authors.initials: MA
authors.lastname: Little
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, UK.
authors.forename: Valentina
authors.identifier: http://orcid.org/0000-0002-4078-6517
authors.initials: V
authors.lastname: Santolini
authors.affiliation: Department of Chemistry and Materials Innovation Factory, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.
authors.forename: Samantha Y
authors.identifier: http://orcid.org/0000-0002-3095-875X
authors.initials: SY
authors.lastname: Chong
authors.affiliation: Department of Chemistry and Materials Innovation Factory, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.
authors.forename: Tom
authors.identifier: http://orcid.org/0000-0003-4736-0604
authors.initials: T
authors.lastname: Hasell
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, UK.
authors.forename: Kim E
authors.initials: KE
authors.lastname: Jelfs
authors.affiliation: Department of Chemistry and Materials Innovation Factory, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK. mebriggs@liverpool.ac.uk.
authors.forename: Michael E
authors.identifier: http://orcid.org/0000-0003-1474-1267
authors.initials: ME
authors.lastname: Briggs
authors.affiliation: Department of Chemistry and Materials Innovation Factory, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK. aicooper@liverpool.ac.uk.
authors.forename: Andrew I
authors.initials: AI
authors.lastname: Cooper
keywords: cage compounds; cycloimination; gas sorption; microporous materials