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CFAP540 and CFAP700, with high selectivity and sensitivity to FA, are, respectively, suitable in cell and in vivo. Experimentalists have confirmed that both probes utilize a general 2\u2010aza\u2010Cope FA\u2010reactive trigger and a chemiluminogenic phenoxydioxetane scaffold. The mechanism and detailed process of CFAP chemiluminescence (CL) remain largely unknown. In the present paper, (time\u2010dependent) density functional theory calculations are performed on the entire reaction process of CFAP540 with FA to produce CL. The calculations elucidated the CL\u2010producing process: FA initiates the decomposition of CFAP540 by dehydration condensation, and a phenoxy 1,2\u2010dioxetane is formed through a series of reactions of aza\u2010Cope rearrangement, hydrolysis of imine, and \u03b2\u2010elimination of alkoxyl group. Afterwards, the produced phenoxy 1,2\u2010dioxetane decomposes to produce the <jats:italic>m<\/jats:italic>\u2010oxybenzoate derivative in the first singlet state (S<jats:sub>1<\/jats:sub>) via two crossings between potential energy surfaces of the ground state (S<jats:sub>0<\/jats:sub>) and S<jats:sub>1<\/jats:sub> state. This <jats:italic>m<\/jats:italic>\u2010oxybenzoate derivative was assigned as the light emitter of the CFAP540 CL. The CL\u2010producing process and assignment of the light emitter of CFAP700 CL are similar with the corresponding ones of CFAP540. By analyzing the D\u2010\u03c0\u2010A architecture of the light emitters of CFAP540 and CFAP700, a series of CFAPs is theoretically designed and a scheme to modulate their CL from visible to near\u2010infrared region is proposed by adjusting the length and structure of the \u03c0\u2010bridge.<\/jats:p>","DOI":"10.1002\/chem.202004556","type":"journal-article","created":{"date-parts":[[2020,12,3]],"date-time":"2020-12-03T10:02:26Z","timestamp":1606989746000},"page":"5712-5720","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Mechanistic Investigation on Chemiluminescent Formaldehyde Probes"],"prefix":"10.1002","volume":"27","author":[{"given":"Shuangqi","family":"Pi","sequence":"first","affiliation":[{"name":"Key Laboratory of Theoretical and Computational Photochemistry Ministry of Education College of Chemistry Beijing Normal University  Beijing 100875 P. R. China), E-mail: yajun"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Quansong","family":"Li","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Beijing Institute of Technology  Beijing 100081 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ling","family":"Yue","sequence":"additional","affiliation":[{"name":"Key Laboratory for Non-Equilibrium Synthesis and Modulation of, Condensed Matter Ministry of Education School of Chemistry Xi'an Jiaotong University  Xi'an, Shaanxi 710049 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8761-5339","authenticated-orcid":false,"given":"Ya\u2010Jun","family":"Liu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Theoretical and Computational Photochemistry Ministry of Education College of Chemistry Beijing Normal University  Beijing 100875 P. R. 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