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- Title
Revisiting the Ullman's Radical Chemistry for Phthalocyanine Derivatives.
- Authors
Fidan, Ismail; Luneau, Dominique; Ahsen, Vefa; Hirel, Catherine
- Abstract
Abstract: Phthalocyanine derivatives do not cease to gain attention due to their numerous properties and applications (e.g., sensor, PDT). This makes them a unique scaffold for the design of new material. In this context, we were interested to develop the synthesis of an imino nitroxide‐substituted phthalocyanine by Ullman's procedure; a challenge due to the intrinsic low solubility of most phthalocyanine derivative in much solvents. To overcome this solubility problem, we designed a phthalocyanine with bulky neopentyl substituents in peripheral positions as counterpart to the imino nitroxide moieties. The imino nitroxide‐substituted phthalocyanine was obtained by condensation of a monoformyl‐substituted phthalocyanine with 2,3‐bis(hydroxylamino)‐2,3‐dimethylbutane in refluxing THF–MeOH (2:1) mixture in the presence of <italic>p</italic>‐toluenesulfonic acid monohydrate, follow by oxidation with PbO2. Characterization was performed by electrochemistry, UV/Vis and EPR spectroscopy in solution as well as SQUID in solid state.
- Subjects
PHTHALOCYANINE derivatives; ORGANIC compound derivatives; IMINO group; NITROXIDE derivatives; MOIETIES (Chemistry)
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 20, p5359
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201704903