Two　novel　metal-free　organic　dyes,　namely　the　mono-anchoring　KMT1　and　di-anchoring　KMT2　dyes,　have　been　synthesized　to　function　as　photosensitizers　for　utilizing　in　photocatalytic　hydrogen　production　systems.　They　adopt　the　donor-donor-π-acceptor　and　donor-donor-(−π-acceptor)2　configurations,　respectively,　featuring　triphenylamine　and　fluorene　moieties　as　electron　donors,　thiophene　as　the　π-bridges　and　cyanoacrylic　acid　as　the　acceptors/anchoring　groups.　It　was　found　that　the　photocatalytic　performance　of　the　di-anchoring　dye　significantly　outperforms　that　of　its　mono-anchoring　counterpart.　KMT2-based　photocatalytic　system　demonstrated　remarkable　performance,　producing　3520　μmol　(84.9　mL)　of　hydrogen　over　a　span　of　257　hours　under　blue　light　irradiation,　with　a　turnover　number　(TON)　of　56300,　a　turnover　frequency　(TOFi)　of　1862.7　h−1,　an　initial　hydrogen　production　activity　(activityi)　of　1164180　and　an　apparent　quantum　yield　(AQYi　%)　of　19.9.　This　performance　is　among　the　top-tier　when　compared　to　other　dyes　used　in　similar　photocatalytic　systems.　The　results　clearly　illustrate　that　the　di-anchoring　dye　possesses　several　advantages,　including　a　broad　absorption　spectrum,　higher　absorptivity,　and　a　relatively　slower　charge　recombination　rate.　These　attributes　collectively　contribute　to　its　superior　overall　performance　in　photocatalysis.　©　2024　Wiley-VCH　GmbH.