Fluorescent properties of sulfamethoxazole with an emphasis on photobasicity and dual emission of its deprotonated (anionic) form

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Fluorescent properties of sulfamethoxazole with an emphasis on photobasicity and dual emission of its deprotonated (anionic) form. / Tsay, Ivan E.; Novikov, Mikhail V.; Pozdnyakov, Ivan P.

In: Journal of Luminescence, Vol. 294, 121888, 06.2026.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{bee3e9ca7fd643a5849a2d42a5a02ec2,

title = "Fluorescent properties of sulfamethoxazole with an emphasis on photobasicity and dual emission of its deprotonated (anionic) form",

abstract = "Fluorescence properties of popular antibiotic sulfamethoxazole (SMX) and its anionic form were studied in a wide set of solvents. The anionic form has demonstrated photobasicity, i.e. increase of basicity in the excited state, and dual fluorescence emission with large Stokes shift in the aqueous solution. The excited state pKa∗ of SMX was determined as 13.2 when the ground state pKa is 5.7 only. The anionic form of sulfanilamide (unsubstituted analogue of SMX) demonstrates dual emission as well. Based on TD-DFT calculations of the anionic form of sulfanilamide, we have proposed and discussed possible causes of dual fluorescence of SMX. These findings can be useful to explain photophysics of other sulfanilamide anions in solution.",

keywords = "Dual fluorescence, Large Stokes shift, Photobasicity, Sulfa drugs, Sulfamethoxazole, Sulfanilamide, Двойная флуоресценция, Фотоосновность, Сульфаметоксазол, Сульфаниламид, Сульфаниламидные препараты, Большой стоксов сдвиг",

author = "Tsay, {Ivan E.} and Novikov, {Mikhail V.} and Pozdnyakov, {Ivan P.}",

note = "Ivan E. Tsay, Mikhail V. Novikov, Ivan P. Pozdnyakov, Fluorescent properties of sulfamethoxazole with an emphasis on photobasicity and dual emission of its deprotonated (anionic) form, Journal of Luminescence, Volume 294, 2026, 121888, ISSN 0022-2313, https://doi.org/10.1016/j.jlumin.2026.121888. – EDN GFBNCZ. I.E.T., M.V.N. and I.P.P. (Voevodsky Institute of Chemical Kinetics and Combustion SB RAS) acknowledge the core funding from the Russian Federal Ministry of Science and Higher Education (FWGF-2026- 0011). Authors acknowledge Laboratory of Nitrogen Compounds of N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry for kindly provided sulfanilamide for the fluorescence experiments. Computational resources for DFT calculations were provided by the Computational Center of Novosibirsk State University.",

year = "2026",

month = jun,

doi = "10.1016/j.jlumin.2026.121888",

language = "English",

volume = "294",

journal = "Journal of Luminescence",

issn = "0022-2313",

publisher = "Elsevier Science Publishing Company, Inc.",

}

RIS

TY - JOUR

T1 - Fluorescent properties of sulfamethoxazole with an emphasis on photobasicity and dual emission of its deprotonated (anionic) form

AU - Tsay, Ivan E.

AU - Novikov, Mikhail V.

AU - Pozdnyakov, Ivan P.

N1 - Ivan E. Tsay, Mikhail V. Novikov, Ivan P. Pozdnyakov, Fluorescent properties of sulfamethoxazole with an emphasis on photobasicity and dual emission of its deprotonated (anionic) form, Journal of Luminescence, Volume 294, 2026, 121888, ISSN 0022-2313, https://doi.org/10.1016/j.jlumin.2026.121888. – EDN GFBNCZ. I.E.T., M.V.N. and I.P.P. (Voevodsky Institute of Chemical Kinetics and Combustion SB RAS) acknowledge the core funding from the Russian Federal Ministry of Science and Higher Education (FWGF-2026- 0011). Authors acknowledge Laboratory of Nitrogen Compounds of N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry for kindly provided sulfanilamide for the fluorescence experiments. Computational resources for DFT calculations were provided by the Computational Center of Novosibirsk State University.

PY - 2026/6

Y1 - 2026/6

N2 - Fluorescence properties of popular antibiotic sulfamethoxazole (SMX) and its anionic form were studied in a wide set of solvents. The anionic form has demonstrated photobasicity, i.e. increase of basicity in the excited state, and dual fluorescence emission with large Stokes shift in the aqueous solution. The excited state pKa∗ of SMX was determined as 13.2 when the ground state pKa is 5.7 only. The anionic form of sulfanilamide (unsubstituted analogue of SMX) demonstrates dual emission as well. Based on TD-DFT calculations of the anionic form of sulfanilamide, we have proposed and discussed possible causes of dual fluorescence of SMX. These findings can be useful to explain photophysics of other sulfanilamide anions in solution.

AB - Fluorescence properties of popular antibiotic sulfamethoxazole (SMX) and its anionic form were studied in a wide set of solvents. The anionic form has demonstrated photobasicity, i.e. increase of basicity in the excited state, and dual fluorescence emission with large Stokes shift in the aqueous solution. The excited state pKa∗ of SMX was determined as 13.2 when the ground state pKa is 5.7 only. The anionic form of sulfanilamide (unsubstituted analogue of SMX) demonstrates dual emission as well. Based on TD-DFT calculations of the anionic form of sulfanilamide, we have proposed and discussed possible causes of dual fluorescence of SMX. These findings can be useful to explain photophysics of other sulfanilamide anions in solution.

KW - Dual fluorescence

KW - Large Stokes shift

KW - Photobasicity

KW - Sulfa drugs

KW - Sulfamethoxazole

KW - Sulfanilamide

KW - Двойная флуоресценция

KW - Фотоосновность

KW - Сульфаметоксазол

KW - Сульфаниламид

KW - Сульфаниламидные препараты

KW - Большой стоксов сдвиг

UR - https://www.mendeley.com/catalogue/92fd08f5-5607-3f5a-bcad-8eee60aefa52/

UR - https://www.scopus.com/pages/publications/105034621798

UR - https://elibrary.ru/item.asp?id=90965812

U2 - 10.1016/j.jlumin.2026.121888

DO - 10.1016/j.jlumin.2026.121888

M3 - Article

VL - 294

JO - Journal of Luminescence

JF - Journal of Luminescence

SN - 0022-2313

M1 - 121888

ER -

ID: 85025942