Terekhov, DmitriD'Ascanio, Anna M.ISAGO, HiroakiLi, ZhaopengLeznoff, Clifford C.2011-01-142011-01-141999J. Porphyrins and Phthalocyanines, 1999, 3, 406-416http://hdl.handle.net/10315/6605Coupling of 4,5-diiodophthalonitrile with tert-butyldimethylsilylacetylene and a palladium catalyst gave 4,5-bis(tert-butyldimethylsilylethynyl)phthalonitrile. Cleavage of the silyl moiety with tetftibutylammonium 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-wtakis(tert-butyldimethylsilylethynyl)phthalocyanine or its zinc derivative. Cleavage of the silyl groups of the zinc derivative gave an insoluble product whose tH NMR spectrum was indicative of 2,3,9,10,16,17,23,?A.-octaettrynylphthalocyaninato zinc(Il). Bromination of phthalonitrile withN,lV{ibromoisocyanuric acid gave a separable mixture of 3,6-,3,21- and 4,S-dibromophthalonitrile along with the monobromophthalonitrites. Coupling of 3,4dibromophalonitrile with ren-butylacetylene gave 3,4-bis(ren-butylethynyl)phthalonitrile, which on condensation with lithium lpentanolate gave 1,2,8,9,15,16,22,23-octzkjs(3,3-dimethyl-l-butynyl)phthalocyanins as a single isomer, the first known 1,2,8,9,15.16,22,23-octasubstituted phthalocyanine.enArticlehttp://onlinelibrary.wiley.com/doi/10.1002/(SICI)1099-1409(199908/10)3:6/7%3C406