We　design　and　synthesize　a　series　of　novel　silicon(IV)　phthalocyanines　(SiPcs,　1a,　2a,　1b,　and　2b)　axially　conjugated　with　arginine　or　arginine-containing　oligopeptides　(Arg-Arg,　Cys-Arg,　Cys-Arg-Arg)　through　ester　or　ether　linkers　to　demonstrate　the　effects　of　substituents　and　coupling　ways　on　the　spectral　behaviors　and　photodynamic　activities.　The　ester-linked　SiPcs　(1a　and　2a)　show　slight　red-shift,　higher　fluorescence　emission　and　singlet　oxygen　generation　compared　to　the　ether-linked　analogues　(1b　and　2b)　due　to　the　stronger　electron-withdrawing　ability　of　the　ester　group,　suggesting　that　electronic　effect　of　the　linkers　plays　an　important　role　in　their　spectral　properties.　The　introduction　of　arginine　could　effectively　reduce　the　aggregation　of　phthalocyanine　in　aqueous　solutions.　With　higher　cellular　uptake　and　plasma　membrane　localization　ability,　1b　and　2b　exhibit　significantly　higher　photocytotoxicity　against　both　HepG2　and　Hela　cells.　Moreover,　the　in　vivo　fluorescence　imaging　suggests　that　2b　is　the　most　specific　toward　H22　tumor-bearing　ICR　mice,　and　it　shows　efficient　tumor　growth　inhibition　with　the　tumor　inhibition　rate　up　to　93%.　Thus,　this　work　would　provide　a　new　reference　for　the　development　of　phthalocyanine-based　photosensitizers.　©　2020　Fujian　Institute　of　Research　of　the　Structure　of　Matter.　All　rights　reserved.