{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Lapesova J"],"funding":["European Research Council","Ministerstvo ?kolstv?, Ml?de?e a Telov?chovy","Grantov? Agentura, Univerzita Karlova"],"pagination":["25077-25088"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC12754792"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["64(51)"],"pubmed_abstract":["Azaphthalocyanines are fluorescent dyes and photosensitizers with promising applications in photodynamic therapy (PDT) and fluorescence sensing. However, achieving precise control over their photophysical behavior remains a major challenge. Here, we report a supramolecular approach to enhance fluorescence quenching via charge-transfer complex formation. An electron-deficient azaphthalocyanine derivative incorporating a naphthalene-2,6-diol moiety as a charge-transfer donor was synthesized, and its fluorescence response toward a tailored quencher was evaluated. A ferrocene-methylviologen conjugate that simultaneously functions as a quencher and an acceptor in charge-transfer complexes was designed and synthesized for this purpose. Compared to ferrocenemethanol and methylviologen alone, the conjugate quencher exhibited an enhanced quenching efficiency in acetonitrile. The quenching followed a nonlinear Stern-Volmer dependence, indicating both static and dynamic quenching mechanisms, with the former one being more efficient with <i>K</i><sub>S</sub> = 241 M<sup>-1</sup> due to directed charge-transfer complex formation between methylviologen and the naphthalene-2,6-diol moiety serving as a staple. These findings demonstrate that complexation can enhance the fluorescence quenching of AzaPc derivatives and suggest a general approach for designing responsive photosensitizers in smart PDT systems or molecular sensing."],"journal":["Inorganic chemistry"],"pubmed_title":["Enhanced Quenching in an Azaphthalocyanine-Ferrocene Supramolecular Dyad upon Charge-Transfer Complex Formation."],"pmcid":["PMC12754792"],"funding_grant_id":["170223","101041554","LL2318","CZ.02.01.01/00/22_008/0004607"],"pubmed_authors":["Slanina T","Ludvikova L","Demuth J","Zimcik P","Novakova V","Lapesova J"],"additional_accession":[]},"is_claimable":false,"name":"Enhanced Quenching in an Azaphthalocyanine-Ferrocene Supramolecular Dyad upon Charge-Transfer Complex Formation.","description":"Azaphthalocyanines are fluorescent dyes and photosensitizers with promising applications in photodynamic therapy (PDT) and fluorescence sensing. However, achieving precise control over their photophysical behavior remains a major challenge. Here, we report a supramolecular approach to enhance fluorescence quenching via charge-transfer complex formation. An electron-deficient azaphthalocyanine derivative incorporating a naphthalene-2,6-diol moiety as a charge-transfer donor was synthesized, and its fluorescence response toward a tailored quencher was evaluated. A ferrocene-methylviologen conjugate that simultaneously functions as a quencher and an acceptor in charge-transfer complexes was designed and synthesized for this purpose. Compared to ferrocenemethanol and methylviologen alone, the conjugate quencher exhibited an enhanced quenching efficiency in acetonitrile. The quenching followed a nonlinear Stern-Volmer dependence, indicating both static and dynamic quenching mechanisms, with the former one being more efficient with <i>K</i><sub>S</sub> = 241 M<sup>-1</sup> due to directed charge-transfer complex formation between methylviologen and the naphthalene-2,6-diol moiety serving as a staple. These findings demonstrate that complexation can enhance the fluorescence quenching of AzaPc derivatives and suggest a general approach for designing responsive photosensitizers in smart PDT systems or molecular sensing.","dates":{"release":"2025-01-01T00:00:00Z","publication":"2025 Dec","modification":"2026-06-06T08:25:25.11Z","creation":"2026-05-27T03:11:51.973Z"},"accession":"S-EPMC12754792","cross_references":{"pubmed":["41392693"],"doi":["10.1021/acs.inorgchem.5c03733"]}}