In:
Journal of Porphyrins and Phthalocyanines, World Scientific Pub Co Pte Ltd, Vol. 03, No. 06 ( 1999-08), p. 406-416
Abstract:
Coupling of 4,5-diiodophthalonitrile with tert-butyldimethylsilylacetylene and a palladium catalyst gave 4,5-bis(tert-butyldimethylsilylethynyl)phthalonitrile. Cleavage of the silyl moiety with tetrabutylammonium fluoride gave 4,5-diethynylphthalonitrile, while condensation in 2-N,N-dimethylaminoethanol without or with Zn ( OAc ) 2 gave metal-free 2,3,8,9,16,17,23,24-octakis(tert-butyldimethylsilylethynyl)phthalocyanine or its zinc derivative. Cleavage of the silyl groups of the zinc derivative gave an insoluble product whose 1 H NMR spectrum was indicative of 2,3,9,10,16,17,23,24-octaethynylphthalocyaninato zinc(II). Bromination of phthalonitrile with N,N-dibromoisocyanuric acid gave a separable mixture of 3,6-, 3,4- and 4,5-dibromophthalonitrile along with the monobromophthalonitriles. Coupling of 3,4-dibromophalonitrile with tert-butylacetylene gave 3,4-bis(tert-butylethynyl)phthalonitrile, which on condensation with lithium 1-pentanolate gave 1,2,8,9,15,16,22,23-octakis(3,3-dimethyl-1-butynyl)phthalocyanine as a single isomer, the first known 1,2,8,9,15,16,22,23-octasubstituted phthalocyanine.
Type of Medium:
Online Resource
ISSN:
1088-4246
,
1099-1409
DOI:
10.1002/(SICI)1099-1409(199908/10)3:6/7〈406::AID-JPP149〉3.0.CO;2-U
Language:
English
Publisher:
World Scientific Pub Co Pte Ltd
Publication Date:
1999
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