The synthesis and characterisation of carbohydrate-functionalised porphyrazines

Williams, DBG; Mbatha, GB

The synthesis and characterisation of carbohydrate-functionalised porphyrazines

Williams, DBG

Mbatha, GB

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Publication Type:: Journal Article
Citation:: Dyes and Pigments, 2011, 88 (1), pp. 65 - 74
Issue Date:: 2011-01-01

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Field	Value	Language
dc.contributor.author	Williams, DBG https://orcid.org/0000-0002-3703-6301	en_US
dc.contributor.author	Mbatha, GB	en_US
dc.date.issued	2011-01-01	en_US
dc.identifier.citation	Dyes and Pigments, 2011, 88 (1), pp. 65 - 74	en_US
dc.identifier.issn	0143-7208	en_US
dc.identifier.uri	http://hdl.handle.net/10453/116075
dc.description.abstract	A synthetic pathway to the incorporation of mono- and disaccharide carbohydrate moieties into porphyrazine systems was demonstrated. A range of selectively protected monosaccharide precursors was coupled to a small variety of phthalonitriles; the intermediates were co-macrocyclised to form hybrid porphyrazines in Linstead macrocyclisation reactions. Demetallisation of Mg-porphyrazine products was readily effected to afford the free-base pigments, which were subsequently converted into their zinc or nickel complexes. Some porphyrazines were deprotected of their isopropylidene groups (on the carbohydrate moieties) under acidic conditions to reveal polar OH groups. The extraction coefficients of the porphyrazines between 2-octanol and phosphate buffered saline solution were measured. Comparison of the partition coefficients of the carbohydrate-substituted porphyrazines and their deprotected counterparts revealed that structural alteration offers a way to significantly increase the hydrophilicity of substituted porphyrazines. © 2010 Elsevier Ltd. All rights reserved.	en_US
dc.relation.ispartof	Dyes and Pigments	en_US
dc.relation.isbasedon	10.1016/j.dyepig.2010.05.002	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	The synthesis and characterisation of carbohydrate-functionalised porphyrazines	en_US
dc.type	Journal Article
utslib.citation.volume	1	en_US
utslib.citation.volume	88	en_US
utslib.for	0904 Chemical Engineering	en_US
utslib.for	0306 Physical Chemistry (incl. Structural)	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
utslib.copyright.status	closed_access
pubs.issue	1	en_US
pubs.publication-status	Published	en_US
pubs.volume	88	en_US

Abstract:

A synthetic pathway to the incorporation of mono- and disaccharide carbohydrate moieties into porphyrazine systems was demonstrated. A range of selectively protected monosaccharide precursors was coupled to a small variety of phthalonitriles; the intermediates were co-macrocyclised to form hybrid porphyrazines in Linstead macrocyclisation reactions. Demetallisation of Mg-porphyrazine products was readily effected to afford the free-base pigments, which were subsequently converted into their zinc or nickel complexes. Some porphyrazines were deprotected of their isopropylidene groups (on the carbohydrate moieties) under acidic conditions to reveal polar OH groups. The extraction coefficients of the porphyrazines between 2-octanol and phosphate buffered saline solution were measured. Comparison of the partition coefficients of the carbohydrate-substituted porphyrazines and their deprotected counterparts revealed that structural alteration offers a way to significantly increase the hydrophilicity of substituted porphyrazines. © 2010 Elsevier Ltd. All rights reserved.

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http://hdl.handle.net/10453/116075