＂Smar＂　targeted　photosensitizer　conjugated　with　small　molecule　target-based　anticancer　drug　which　has　a　simple　chemical　structure　and　high　stability,　is　a　new　promising　targeted　therapeutic　strategy.　We　herein　extended　this　strategy　and　reported　a　novel　series　of　zinc(II)　phthalocyanine-erlotinib　analogue　conjugates　with　different　peripheral　substituted　positions　and　lengths　of　the　linker.　Having　erlotinib　analogue　as　the　targeting　moiety,　all　conjugates　exhibited　high　specificity　and　potent　affinity　to　HepG2　cancer　cells　and　kept　high　photodynamic　activity　(IC50=3.7–16.7　nmol/L).　Structure-activity　relationships　of　these　conjugates　were　assessed　by　investigating　their　photophysical/photochemical　properties,　targeting　intracellular　uptake　and　in　vitro　phototoxicity.　The　results　suggested　that　α-substituted　conjugates　showed　slightly　higher　photodynamic　activity　than　β-substituted　ones.　In　conclusion,　we　have　developed　a　series　of　promising　anticancer　agents　with　high　tumor　selectivity　and　anticancer　activity　for　targeted　photodynamic　therapy.　Copyright　©　2016　SIOC,　CAS,　Shanghai　&　WILEY-VCH　Verlag　GmbH　&　Co.　KGaA,　Weinheim