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Synthesis of water soluble PEGylated (copper) phthalocyanines via Mitsunobu reaction and Cu(i)-catalysed azide–alkyne cycloaddition (CuAAC) “click” chemistry
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Li, Muxiu, Khoshdel, Ezat and Haddleton, David M. (2013) Synthesis of water soluble PEGylated (copper) phthalocyanines via Mitsunobu reaction and Cu(i)-catalysed azide–alkyne cycloaddition (CuAAC) “click” chemistry. Polymer Chemistry, Volume 4 (Number 16). pp. 4405-4411. doi:10.1039/c3py00609c ISSN 1759-9954.
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Official URL: http://dx.doi.org/10.1039/c3py00609c
Abstract
Octa-substituted phthalocyanine (Pc) and copper phthalocyanine (CuPc) with different chain lengths of monomethyl ether polyethylene glycol (mPEG) with molecular weights of 350, 550, 750, and up to 2000 g mol-1 were synthesised through combining a phenolic Mitsunobu reaction with Cu(i)-catalysed azide-alkyne cycloaddition (CuAAC) click chemistry. Analysis by GPC shows that narrow polydispersities (PDI ≤ 1.2) of the resultant polymeric derivatives can be achieved; photodiode array (PDA) detection confirms the formation of the desired products. The metal-free Pc polymers are clearly distinguished from polymers functionalised with CuPcs. All PEGylated (Cu)Pc polymers are highly soluble in a range of solvents and show no evidence of aggregation in common organic solvents such as chloroform, DCM, THF, etc. with a split intense Q band between 670 and 690 nm for the mPEG-Pc polymers, and a single Q band at 682 nm for the mPEG-CuPc complexes. The UV-Vis spectra of these polymers in water demonstrate that dimeric complexes are formed in all cases with a minor contribution of monomeric also found in octa-substituted mPEG-CuPc products. More remarkably, the PEGylated (Cu)Pcs with different PEG chain lengths exhibit interesting tunable thermal properties as evidenced by differential scanning calorimetry (DSC).
Item Type: | Journal Article | ||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Polymer Chemistry | ||||
Publisher: | Royal Society of Chemistry | ||||
ISSN: | 1759-9954 | ||||
Official Date: | 21 August 2013 | ||||
Dates: |
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Volume: | Volume 4 | ||||
Number: | Number 16 | ||||
Page Range: | pp. 4405-4411 | ||||
DOI: | 10.1039/c3py00609c | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
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