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Periphery‐Functionalized Porous Organic Cages
Author(s) -
Reiss Paul S.,
Little Marc A.,
Santolini Valentina,
Chong Samantha Y.,
Hasell Tom,
Jelfs Kim E.,
Briggs Michael E.,
Cooper Andrew I.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603593
Subject(s) - cage , porosity , imine , molecule , chemical engineering , porous medium , surface modification , chemistry , materials science , polymer chemistry , nanotechnology , organic chemistry , structural engineering , catalysis , engineering
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.