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A non-planar, hexadeca-substituted, metal-free phthalocyanine

McKeown, Neil B., Li, Hong and Helliwell, Madeleine 2005. A non-planar, hexadeca-substituted, metal-free phthalocyanine. Journal of Porphyrins and Phthalocyanines 09 (12) , pp. 841-845. 10.1142/S1088424605000964

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The readily prepared 2,3,9,10,16,17,23,24-octamethyl-1,4,8,11,15,18,22,25-octaoctyloxyphthalocyanine (Pc 1) adopts a non-planar conformation in the crystalline state as indicated by a dihedral angle of 27.2° formed between isoindole subunits on opposite sides of the core. The ring distortion can be attributed to a combination of steric congestion of the side-chains and the stabilization of the saddle-shaped conformation via pairing of molecules to give the so-called 'overlap effect'. The ring distortion is compared to that found in other metal-free phthalocyanines. Pc 1 adsorbs strongly in the near-IR region, is highly soluble and gives robust spin-coated films of excellent optical clarity.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: phthalocyanine; non-planar; crystal structure
Publisher: WorldSciNet
ISSN: 1088-4246
Last Modified: 19 Mar 2016 23:12

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