Traditional　fluorescent　probes　typically　display　blueshifted　emission　in　rigidifying　media;　however,　a　newly　developed　class　of　rigidochromic　fluorophores　derived　from　phenanthridine　demonstrates　remarkable　redshifted　emission　under　similar　conditions.　Pyridine,　with　similar　N-heterostructure　to　those　of　phenanthridine　group,　is　considered　a　promising　candidate　for　achieving　comparable　rigidity-induced　redshift　behavior.　In　this　work,　we　synthesized　eight　organic　fluorophores　featuring　diverse　functional　units　and　substitutes　by　systematically　combining　pyridine　with　carbazole,　triazatruxene　(TAT),　and　tetraphenylethylene　(TPE),　respectively.　These　molecules　exhibit　significant　emission　redshifts　(up　to　225　nm,　a　record　high　value　ever　reported)　or　notable　emission　intensity　changes　as　the　rigidity　of　the　polymer　matrix　increases,　along　with　unique　acid　responsiveness.　The　differences　in　polar-π　interactions　between　fluorophores　and　polymers　diversify　the　emission　behavior,　advancing　the　development　of　secure　printing　and　intelligent　optical　materials.　By　embedding　these　fluorophores　into　polymer　films　with　helical　phase　structures,　redshifted　emission　with　tunable　chirality　was　achieved.　Notably,　leveraging　the　acid-responsive　properties　of　these　fluorophores,　a　time-dependent　light-controlled　dynamic　encryption　system　was　constructed,　successfully　enabling　multi-level　information　encryption.　This　research　greatly　expands　the　scope　of　rigidochromic　fluorophores,　and　their　applications　in　anti-counterfeiting　and　information　storage.　©　2025　SIOC,　CAS,　Shanghai,　&　WILEY-VCH　GmbH.