168299-95-4Relevant articles and documents
Phthalocyanines with phosphonate moiety via C-nucleophilic substitution in phthalonitriles
Negrimovsky, Vladimir,Komissarov, Aleksey,Perepukhov, Alexandr,Suponitsky, Kyrill,Perevalov, Valery,Lukyanets, Evgeny
, p. 587 - 595 (2013/09/02)
Interaction of isomeric 4-nitro- or 3-nitrophthalonitrile with triethyl phosphonoacetate, diethyl cyanomethylphosphonate or tetraethyl methylenediphosphonate in basic conditions resulted in regioselective C-nucleophilic oxidative substitution of hydrogen ortho-located to nitro group, new phthalonitriles with diethoxyphosphorylmethyl or bis(diethoxyphosphoryl) methyl group were isolated in modest yields. In the same conditions one chlorine atom of tetrachlorophthalonitrile was regioselectively substituted with triethyl phosphonoacetate. In basic conditions, both parent phthalonitriles and corresponding zinc phthalocyanines with ortho-located nitro and diethoxyphosphoryl substituted methyl groups are involved in reversible acid-base interaction accompanied with large bathochromic shift of their long wavelength absorption maxima in visible or NIR region, correspondingly. Formation of tetraazachlorin- and tetraaza(iso)bacteriochlorin-like anions is proposed for explanation of this unprecedent bathochromic shift for phthalocyanines.
Multisubstituted phthalonitriles, naphthalenecicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanide syntheses
Leznoff, Clifford C.,Terekhov, Dmitri S.,McArtur, Colin R.,Vigh, Steven,Li, Jing
, p. 435 - 443 (2007/10/02)
Electrophilic aromatic nitration under mild conditions of 4-hydroxyphthalonitrile gave 4-hydroxy-3-nitrophthalonitrile and 4-hydroxy-5-nitrophthalonitrile, while bromination yielded 3-bromo-4-hydroxyphthalonitrile, 4-bromo-5-hydroxyphthalonitrile, and 3,5-dibromo-4-hydroxyphthalonitrile.Iodination gave 4-hydroxy-5-iodophthalonitrile and 4-hydroxy-3,5-diiodophthalonitrile.Coupling of 4-iodophthalonitrile, 3-iodophthalonitrile, and 5-iodo-2,3-dicyanonaphthalene with trans-1,2-bis(tri-n-butylstannyl)ethene gave trans-1,2-bis(3,4-dicyanophenyl)ethene, trans-1,2-bis(2,3-dicyanophenyl) ethene, and trans-1,2-bis(6,7-dicyanonaphthyl)ethene.Photocyclization of a dilute solution of cis-or trans-1,2bis(3,4-dicyanophenyl)ethene in dioxane gave a 1:1 mixture of 2,3,6,7- and 2,3,5,6,-tetracyanophenanthrenes separable by chromatography.Key words: phthalonitriles, naphthalenedicarbonitriles, phenanthrenetetracarbonitriles, electrophilic substitution.