Periphery-Functionalized Porous Organic Cages

Paul S. Reiss; Marc A. Little; Valentina Santolini; Samantha Y. Chong; Tom Hasell; Kim E. Jelfs; Michael E. Briggs; Andrew I. Cooper

doi:10.1002/chem.201603593

Periphery-Functionalized Porous Organic Cages

Paul S. Reiss, Marc A. Little, Valentina Santolini, Samantha Y. Chong, Tom Hasell, Kim E. Jelfs, Michael E. Briggs^*, Andrew I. Cooper

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

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.

Original language	English
Pages (from-to)	16547-16553
Number of pages	7
Journal	Chemistry - A European Journal
Volume	22
Issue number	46
DOIs	https://doi.org/10.1002/chem.201603593
Publication status	Published - 7 Nov 2016

Keywords

cage compounds
cycloimination
gas sorption
microporous materials

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201603593

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@article{52efebfcc23f4ff18334ffa92db998bb,

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.",

keywords = "cage compounds, cycloimination, gas sorption, microporous materials",

author = "Reiss, {Paul S.} and Little, {Marc A.} and Valentina Santolini and Chong, {Samantha Y.} and Tom Hasell and Jelfs, {Kim E.} and Briggs, {Michael E.} and Cooper, {Andrew I.}",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = nov,

day = "7",

doi = "10.1002/chem.201603593",

language = "English",

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journal = "Chemistry - A European Journal",

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T1 - Periphery-Functionalized Porous Organic Cages

AU - Reiss, Paul S.

AU - Little, Marc A.

AU - Santolini, Valentina

AU - Chong, Samantha Y.

AU - Hasell, Tom

AU - Jelfs, Kim E.

AU - Briggs, Michael E.

AU - Cooper, Andrew I.

PY - 2016/11/7

Y1 - 2016/11/7

N2 - 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.

AB - 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.

KW - cage compounds

KW - cycloimination

KW - gas sorption

KW - microporous materials

UR - http://www.scopus.com/inward/record.url?scp=84990841893&partnerID=8YFLogxK

U2 - 10.1002/chem.201603593

DO - 10.1002/chem.201603593

M3 - Article

AN - SCOPUS:84990841893

SN - 0947-6539

VL - 22

SP - 16547

EP - 16553

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 46

ER -

Periphery-Functionalized Porous Organic Cages

Abstract

Keywords

ASJC Scopus subject areas

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