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The calculated \u0394<jats:italic>G<\/jats:italic><jats:sub>p<\/jats:sub> energies for amino SBFs in the S<jats:sub>1<\/jats:sub> state range from 985 to 1100\u2009kJ\u2009mol<jats:sup>\u22121<\/jats:sup> which are below the values for guanidines. The protonation of the guanidine\u2010SBFs induces a hypsochromic shift of the absorption and the emission maxima with the Stokes shift of &gt;\u2009100\u2009nm in both cases. Isomerization through the ESIPT process is less probable than in amino\u2010SBFs due to the unfavorable thermodynamics. Still, if it occurs, it leads to a strong red shift of the emission by &gt;\u2009150\u2009nm. Aromaticity indices point to strong antiaromatic character of the examined guanidino\u2010SBFs in the FC region which decreases upon geometrical relaxation and ESIPT. The excited state proton transfer occurs in guanidine\u2010SBF\/phenol complexes in the S<jats:sub>1<\/jats:sub> state, stabilizing CT states and fluorescence quenching.<\/jats:p>","DOI":"10.1002\/jcc.70054","type":"journal-article","created":{"date-parts":[[2025,2,4]],"date-time":"2025-02-04T05:35:26Z","timestamp":1738647326000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Molecular and Electronic Structure and Properties of\u00a0the Single Benzene\u2010Based Fluorophores Containing\u00a0Guanidine Subunit"],"prefix":"10.1002","volume":"46","author":[{"given":"Zoran","family":"Glasovac","sequence":"first","affiliation":[{"name":"Division of Organic Chemistry and Biochemistry Ru\u0111er Bo\u0161kovi\u0107 Institute  Zagreb Croatia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Davor","family":"Margeti\u0107","sequence":"additional","affiliation":[{"name":"Division of Organic Chemistry and Biochemistry Ru\u0111er Bo\u0161kovi\u0107 Institute  Zagreb Croatia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6876-0845","authenticated-orcid":false,"given":"Ivana","family":"Antol","sequence":"additional","affiliation":[{"name":"Division of Organic Chemistry and Biochemistry Ru\u0111er Bo\u0161kovi\u0107 Institute  Zagreb Croatia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,2,3]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.biochem.77.061906.092014"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/smtd.201700191"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.3c00605"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002712"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202100641"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201200027"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2023.111811"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB02387F"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/adom.201900927"},{"key":"e_1_2_7_11_1","first-page":"1","article-title":"Precision Molecular Engineering of Miniaturized Near\u2010Infrared Fluorophores","author":"Huang R.","year":"2024","journal-title":"ChemRxiv"},{"key":"e_1_2_7_12_1","first-page":"59","volume-title":"Progress in Molecular Biology and Translational Science: Chapter\u00a03","author":"Ptaszek M.","year":"2013"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2024.102458"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19123930102"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202403954"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300471v"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-25677-2"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202203748"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.27304"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssensors.1c00876"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.201800247"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.6b05180"},{"key":"e_1_2_7_23_1","volume-title":"Gaussian 16, Revision C.02","author":"Frisch M. 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