{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,15]],"date-time":"2025-12-15T14:21:20Z","timestamp":1765808480875,"version":"build-2065373602"},"reference-count":87,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2025,5,18]],"date-time":"2025-05-18T00:00:00Z","timestamp":1747526400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This paper concerns the in silico studies of the influence of heterocyclic substituents as well as their protonated and deprotonated forms on the spectral characteristics of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) dyes. Computational studies were carried out in order to reveal the most effective method of modeling of the spectral features of fluorescent BODIPY dyes. To perform these studies, the pyrrole and imidazole derivatives of BODIPY dyes were selected, and their spectral features were investigated with DFT and TD-DFT calculations. The calculations showed that the deprotonation of the substituents leads to a bathochromic shift of the calculated absorption wavelength, while the protonation (imidazole derivative) brings about a hypsochromic shift with respect to the neutral form of the dye. The calculated spectral characteristics, considering the influence of the solvent polarity (PCM model), were correlated with the ETN solvatochromic parameter. These correlations show that the increase in the solvent polarity causes a hypsochromic shift of the calculated absorption and emission wavelengths, whereas the bathochromic shift of the wavelengths is observed for the protonated form.<\/jats:p>","DOI":"10.3390\/molecules30102209","type":"journal-article","created":{"date-parts":[[2025,5,19]],"date-time":"2025-05-19T05:37:13Z","timestamp":1747633033000},"page":"2209","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Theoretical Insights into the Impact of Pyrrole and Imidazole Substituents on the BODIPY Chromophore"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3517-568X","authenticated-orcid":false,"given":"Patrycja","family":"Pi\u0119ko\u015b","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4974-7805","authenticated-orcid":false,"given":"Pawe\u0142","family":"Lipkowski","sequence":"additional","affiliation":[{"name":"Department of Physical and Quantum Chemistry, Wroc\u0142aw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9597-0629","authenticated-orcid":false,"given":"Wim","family":"Dehaen","sequence":"additional","affiliation":[{"name":"Department of Chemistry, KU Leuven, Celestijnenlaan 200f-bus 02404, 3001 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3711-8961","authenticated-orcid":false,"given":"Robert","family":"Wieczorek","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1013-4945","authenticated-orcid":false,"given":"Aleksander","family":"Filarowski","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,5,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1184","DOI":"10.1002\/anie.200702070","article-title":"The chemistry of fluorescent bodipy dyes: Versatility unsurpassed","volume":"47","author":"Ulrich","year":"2008","journal-title":"Ang. Chem. Int. Ed."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1130","DOI":"10.1039\/C1CS15132K","article-title":"Fluorescent indicators based on BODIPY","volume":"41","author":"Boens","year":"2012","journal-title":"Chem. Soc. 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