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To investigate alkyl chain effects, we synthesized 1\u2010pyrene substituted with <jats:italic>N,N<\/jats:italic>\u2010dialkylanilines (<jats:bold>C2<\/jats:bold>, <jats:bold>C6<\/jats:bold>, <jats:bold>C10<\/jats:bold>) via Suzuki coupling. Solvatofluorochromic studies revealed a red\u2010shifted fluorescence with increasing solvent polarity, except in chloroform and methanol, attributed to solute\u2013solvent interaction between solvent proton and the nitrogen atom of <jats:italic>N,N<\/jats:italic>\u2010dialkylamine. In chloroform, blue LED irradiation induced light\u2010sensitive transformation, characterized by decreased longer wavelength absorption and emergence of shorter wavelength bands. The resulting photoproduct was identified as a protonated <jats:italic>N,N<\/jats:italic>\u2010dialkylaniline, with chloroform serving as a proton source. This process is exclusive to chloroform among the tested chlorinated solvents. Mechanistically, photoexcitation induces single\u2010electron transfer from <jats:italic>N,N<\/jats:italic>\u2010dialkylaniline to pyrene, generating radical ions that abstract hydrogen from chloroform. Nanosecond transient absorption spectroscopy confirmed the presence of <jats:italic>N,N<\/jats:italic>\u2010dialkylaniline cation and pyrene anion radicals in chloroform but not in THF, highlighting the solvent role in charge separation and stabilizing radical intermediates. The reaction kinetics vary with alkyl chain length, with <jats:bold>C6<\/jats:bold> being the optimal chain length.<\/jats:p>","DOI":"10.1002\/asia.202500553","type":"journal-article","created":{"date-parts":[[2025,8,13]],"date-time":"2025-08-13T19:05:57Z","timestamp":1755111957000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Chloroform\u2010Driven Excited\u2010State Protonation of Pyrene\u2013Dialkylaniline Derivatives Under Visible Light"],"prefix":"10.1002","volume":"20","author":[{"given":"Kumar","family":"Dineshkumar","sequence":"first","affiliation":[{"name":"Centre for Advanced Organic Materials (Sona\u2010AROMA) Department of Chemistry Sona College of Technology  Salem Tamil Nadu 636\u2009012 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Muniappan","family":"Kalipriyadharshini","sequence":"additional","affiliation":[{"name":"Inorganic &amp; Physical Chemistry Laboratory CSIR\u2010Central Leather Research Institute Adyar Chennai Tamil Nadu 600\u2009020 India"},{"name":"Academy of Scientific and Innovative Research (AcSIR)  Ghaziabad Uttar Pradesh 201\u2009002 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masiyappan","family":"Karuppusamy","sequence":"additional","affiliation":[{"name":"Inorganic &amp; 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