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Luciferin is a derivative of oxyluciferin with very similar fluorescence and photoacidic properties. This similarity indicates that luciferin is also expected to be able to form \u03c0\u2013\u03c0 stacking complexes, but no pH\u2010sensitive fluorescence is found for this compound. Here, a theoretical approach is used to rationalize this finding. We have found that luciferin only forms \u03c0\u2013\u03c0 stacking complexes in the ground state at acidic pH. At basic pH and in the excited state, luciferin is present as a dianion. This species is not able to self\u2010aggregate, owing to repulsive electrostatic interactions. Thus, this emissive species is not subject to \u03c0\u2013\u03c0 stacking interactions; this explains its pH\u2010insensitive fluorescence.<\/jats:p>","DOI":"10.1002\/cphc.201402558","type":"journal-article","created":{"date-parts":[[2014,9,18]],"date-time":"2014-09-18T16:04:56Z","timestamp":1411056296000},"page":"3761-3767","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["A Theoretical Analysis of the Potential Role of \u03c0\u2013\u03c0 Stacking Interactions in the Photoprotolytic Cycle of Firefly Luciferin"],"prefix":"10.1002","volume":"15","author":[{"given":"Lu\u00eds","family":"Pinto da Silva","sequence":"first","affiliation":[]},{"given":"Joaquim C. 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