In　order　to　reduce　the　intramolecular　charge-transfer　(ICT)　effect　of　amine　groups　on　the　photophysical　properties　of　zinc　(II)　phthalocyanine　(ZnPc),　tertiary　amines　were　covalently　connected　with　ZnPc　ring　via　ethyl　p-hydroxybenzoate　or　diethyl　5-hydroxyisophthalate.　Six　new　tertiary　amine-modified　ZnPcs　were　therefore　synthesized　and　characterized.　Meanwhile,　the　corresponding　quaternary　ammonium　ZnPcs　were　also　synthesized.　The　effects　of　different　substitution　ways　(mono-substitutions,　symmetrical　tetra-substitutions,　or　asymmetric　tetra-substitutions)　and　the　numbers　of　different　substitutions　on　the　photophysical　and　physicochemical　properties　of　these　ZnPcs　were　studied.　All　twelve　ZnPcs　had　relatively　high　singlet　oxygen　quantum　yields　(ΦΔ　=　0.32–0.68)　and　fluorescence　quantum　yields　(ΦF　=　0.23–0.40),　where　the　amine-containing　substituents　did　not　show　obvious　ICT　effect.　All　ZnPcs　showed　effective　phototoxicity　towards　breast　cancer　cells　(IC50　=　63–366　nmol/L).　Among　them,　three　tetra-substituted　ZnPcs　containing　quaternary　ammonium　groups　(4aN,　4bN　and　4cN)　showed　the　best　in　vitro　anticancer　photodynamic　activities　with　IC50　=　64–76　nmol/L,　which　owned　to　their　relatively　high　cellular　uptake.　The　tumor　inhibition　rate　of　4aN　on　H22　tumor-bearing　mice　reached　87%　(4aN　dose:　3　nmol/g;　light　dose:　685　nm,　135　J/cm2).　©　2023　Elsevier　Ltd