NDLI: Hydrosoluble dendritic poly(ethylene oxide)s with zinc tetraphenylporphyrin branching points as photosensitizers

Content Provider	Royal Society of Chemistry (RSC)
Author	Deffieux, Alain Schappacher, Michel Wirotius, Anne-Laure Ibarboure, Emmanuel McClenaghan, Nathan D. Scarpantonio, Luca
Copyright Year	2013
Abstract	Synthesis of dendrimer-like star-branched poly(ethylene oxide)s (PEOs) with two and three generations having Zn(II) tetraphenylporphyrin (ZnTPP) moieties at the core and at each branching point has been successfully achieved through an iterative convergent approach harnessing “click chemistry”. In the first step, a four-armed poly(ethylene oxide) star-shaped polymer was synthesized by the copper(I)-catalyzed azide–alkyne cycloaddition between α-azido poly(ethylene oxide) branches (N3-PEO-OH) and 5,10,15,20-tetra(propargyloxyphenyl) Zn(II) porphyrin as the core. In the second step, a tetra-armed star PEO bearing 5-(4-phenoxy)-10,15,20-tris(propargyloxyphenyl) Zn(II) porphyrin at each branch end was prepared by divergence of the ω-hydroxyl PEO chain-ends through a Williamson-type etherification reaction. The resulting star PEO with 3 propargyl groups at each arm end was then subjected to a new “click chemistry” reaction with N3-PEO-OH affording the dendrimer star-like PEO of second generation carrying 12 new ω-OH-PEO external branches attached to the four ZnTPP branching points. Repetition of the second step afforded the high molar mass third generation dendrimer-like PEO carrying 36 ω-OH PEO terminal branches with a uniform distribution of 17 zinc tetraphenylporphyrin moieties as internal branching points. The photophysical properties of the resulting polymers in organic or aqueous medium and their efficiency in singlet oxygen generation are reported.
Starting Page	1903
Ending Page	1912
Page Count	10
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	4
Issue Number	6
Journal	Polymer Chemistry
DOI	10.1039/c2py20936e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Propargyl Dendrimer Molar mass Polymer Zinc Cycloaddition Singlet oxygen Porphyrin Discrete uniform distribution Tetraphenylporphyrin Ethylene oxide Click chemistry Copper
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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