Effects of phosphorus(V)-substituted 1,3,4-thiadiazoles on the electronic properties of BODIPY fluorophores

Effects of phosphorus(V)-substituted 1,3,4-thiadiazoles on the electronic properties of BODIPY fluorophores Full article

Journal

New Journal of Chemistry
ISSN: 1369-9261 , E-ISSN: 1144-0546

Output data

Year: 2025, Volume: 49, Number: 36, Pages: 15885-15894 Pages count : 10 DOI: 10.1039/d5nj01910a

Authors

Uvarov Denis Y. ¹ , Lesnikov Vladislav K. ¹ , Golovanov Ivan S. ¹ , Burikov Sergey A. ² , Salnikova Diana I. ³ , Scherbakov Alexander M. ^4,3 , Zavarzin Igor V. ¹ , Volkova Yulia A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia
2	Faculty of Physics, M. V. Lomonosov Moscow State University, Leninskie Gory, Moscow 119991, Russia
3	N. N. Blokhin National Medical Research Center of Oncology, 24 Kashirskoe shosse, 115522 Moscow, Russia
4	Gause Institute of New Antibiotics, 11 ul. Bol'shaya Pirogovskaya, 119021 Moscow, Russia

Phosphoryl-substituted fluorophores are of particular importance due to their outstanding photophysical properties, enabling the design of advanced fluorogenic materials for various applications. This study reports the synthesis and characterization of novel BODIPY derivatives functionalized with phosphorus(V)-substituted thiadiazole moieties at the 2- or 2,6-positions of the fluorophore core. Derivatives bearing phosphine oxide and phosphoramide groups were synthesized by the oxidative cyclization of corresponding formyl-BODIPYs with phosphorylthioformic acid hydrazides. The photophysical properties of the dyes were found to be tuned by changing a phosphoryl substituent and the number of heterocyclic moieties. All the dyes are highly fluorescent with quantum yields of up to 99%, along with bathochromic shifts in the absorption and emission maxima, which are most pronounced for 2,6-bis-substituted BODIPYs. Phosphine oxide-substituted BODIPYs were found to be electrochemically active and nontoxic. To sum up, the presence of phosphorus(V)-substituted 1,3,4-thiadiazoles significantly alters the electronic properties of BODIPY fluorophores, as reflected in their spectral, photophysical, and electrochemical properties.

Uvarov D.Y. , Lesnikov V.K. , Golovanov I.S. , Burikov S.A. , Salnikova D.I. , Scherbakov A.M. , Zavarzin I.V. , Volkova Y.A.
Effects of phosphorus(V)-substituted 1,3,4-thiadiazoles on the electronic properties of BODIPY fluorophores
New Journal of Chemistry. 2025. V.49. N36. P.15885-15894. DOI: 10.1039/d5nj01910a WOS Scopus OpenAlex

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