Effective Conversion of Amide to Carboxylic Acid on Polymers of Intrinsic Microporosity (PIM-1) with Nitrous Acid.

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dc.contributor.author Wu, Wei-Hsuan en
dc.contributor.author Thomas, Paul en
dc.contributor.author Hume, Paul en
dc.contributor.author Jin, Jianyong en
dc.date.accessioned 2018-10-17T00:27:07Z en
dc.date.issued 2018-04-18 en
dc.identifier.citation Membranes 8(2) 18 Apr 2018 en
dc.identifier.issn 2077-0375 en
dc.identifier.uri http://hdl.handle.net/2292/42292 en
dc.description.abstract Carboxylate-functionalised polymers of intrinsic microporosity (C-PIMs) are highly desirable materials for membrane separation applications. The recently reported method to afford C-PIMs was via an extensive base hydrolysis process requiring 360 h. Herein, a novel and effective method to convert PIM-CONH₂ to C-PIM using nitrous acid was studied. The chemical structure of C-PIM was characterised by ¹H NMR, 13C NMR, FTIR, elemental analysis, UV-Vis, TGA and TGA-MS. Complete conversion from amide to carboxylic acid groups was confirmed. Decarboxylation of C-PIM was also successfully studied by TGA-MS for the first time, with a loss of m/z 44 amu (CO₂) observed at the first degradation stage. TGA also revealed decreased thermal stability of C-PIM relative to PIM-CONH₂ under both N₂ and air atmosphere. Gel permeation chromatography (GPC) analysis showed continuous molecular weight degradation of C-PIM with extended reaction time. Aromatic nitration was also observed as a side reaction in some cases. en
dc.format.medium Electronic en
dc.language eng en
dc.relation.ispartofseries Membranes en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Effective Conversion of Amide to Carboxylic Acid on Polymers of Intrinsic Microporosity (PIM-1) with Nitrous Acid. en
dc.type Journal Article en
dc.identifier.doi 10.3390/membranes8020020 en
pubs.issue 2 en
pubs.volume 8 en
dc.rights.holder Copyright: The authors en
dc.identifier.pmid 29670058 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/OpenAccess en
pubs.subtype research-article en
pubs.subtype Journal Article en
pubs.elements-id 738046 en
pubs.org-id Science en
pubs.org-id Chemistry en
dc.identifier.eissn 2077-0375 en
pubs.record-created-at-source-date 2018-04-20 en
pubs.dimensions-id 29670058 en

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