Asymmetric phthalocyanine synthesis by ROMP-capture-release.
Statistical condensation of norbornenyl-tagged phthalonitrile 3 (Pn A) and 4,5-di-4-methoxyphenoxyphthalonitrile 4 (Pn B) followed by ring-opening metathesis polymerization (ROMP) of Pcs AB(3) and B(4) produced asymmetric Pc-appended polymers. Acidic cleavage of the resulting polymers afforded 2,3,9,10,16,17-hexa-(4-methoxyphenoxy)-23-hydroxy Pc 9. A more soluble 2,3,9,10,16,17-hexa-4-pentylphenoxy-23-hydroxy Pc 13 was synthesized by the same strategy and modified with sebacoyl chloride demonstrating that the unmasked hydroxyl site is reactive as a nucleophile.
Chen
Xiaochun
X
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Salmon
Thaddeus R
TR
McGrath
Dominic V
DV
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D054833:Isoindoles; D015394:Molecular Structure; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D007211:Indoles; D054833:Isoindoles; C013647:phthalocyanine