A　series　of　alpha-tetra-substituted　phthalocyanines　(M　=　2H,　Cu,　Co,　Ni)　with　morpholinyl　moieties　and　their　corresponding　quaternized　derivatives　have　been　synthesized.　The　spectroscopic　and　photosensitizing　properties,　photothermal　effects,　aggregation　trend,　and　partition　coefficients　of　these　phthalocyanines　are　evaluated.　Besides,　we　appraised　their　photothermal　and　photodynamic　activities　against　C.　albicans　and　E.　coli　under　nearinfrared　(NIR)　light　irradiation　(680　nm).　The　results　show　that　cationic　phthalocyanines　are　more　efficacies　in　killing　bacteria　and　fungi　than　their　neutral　analogues.　For　copper　(II)　phthalocyanine　4b　and　metal-free　phthalocyanine　7b,　their　photodynamic　activities　play　a　key　role　in　antimicrobial　treatment,　while　for　other　phthalocyanines,　their　photothermal　effects　play　a　major　role.　Moreover,　metal-free　phthalocyanine　7b　exhibits　an　ideal　synergistic　photothermal/photodynamic　antimicrobial　activity　and　shows　the　highest　photocytotoxicity　among　all　the　compounds.　The　IC90　values　of　7b　towards　C.　albicans　and　E.　coli　are　as　low　as　1.12　mu　M　and　0.47　mu　M,　respectively,　while　others　have　IC90　values　ranging　from　3.31　mu　M　to　50　mu　M,　implying　that　7b　would　be　a　good　candidate　for　future　antimicrobial　applications.