Keywords
5-hydroxyisoquinolones
fluorescence
isoquinolones
photoacidity
Stokes shift
TD-DFT
vibrational relaxation
Abstract
Fluorescent properties of 5-hydroxyisoquinolone-3,4,6,7,8- pentacarboxylates and their 4,6,7,8-tetracarboxylate analogs lacking a 3-positioned electron-withdrawing ester group differ substantially. The presence of an electron-withdrawing group at position 3 in the 5-hydroxyisoquinolone system was found crucial for their vibrational relaxation in the anionic forms, which highlights the importance of substitution pattern providing valuable insights for future research in this area.
Funders
Russian Science Foundation
23--23--00624
References
1.
Le Bahers T., Adamo C., Ciofini I.
Journal of Chemical Theory and Computation,
2011
2.
Tolbert L.M., Solntsev K.M.
Accounts of Chemical Research,
2001
3.
Chen Y., Zhao J., Guo H., Xie L.
Journal of Organic Chemistry,
2012
4.
Adamo C., Jacquemin D.
Chemical Society Reviews,
2013
5.
Belyy A.Y., Platonov D.N., Salikov R.F., Trainov K.P., Medvedev M.G., Luponosov Y.N., Svidchenko E.A., Tomilov Y.V.
Dyes and Pigments,
2021
6.
Wu X., Sun X., Guo Z., Tang J., Shen Y., James T.D., Tian H., Zhu W.
Journal of the American Chemical Society,
2014
7.
Liu X., Xu Z., Cole J.M.
Journal of Physical Chemistry C,
2013
8.
Salikov R.F., Belyy A.Y., Trainov K.P., Velmiskina J.A., Medvedev M.G., Korshunov V.M., Taydakov I.V., Platonov D.N., Tomilov Y.V.
Journal of Photochemistry and Photobiology A: Chemistry,
2022
9.
Siano D.B., Metzler D.E.
Journal of Chemical Physics,
1969
10.
Ireland J.F., Wyatt P.A.
Advances in Physical Organic Chemistry,
1976
11.
Martin C.J., Rapenne G., Nakashima T., Kawai T.
Journal of Photochemistry and Photobiology C: Photochemistry Reviews,
2018
12.
Prémont-Schwarz M., Barak T., Pines D., Nibbering E.T., Pines E.
Journal of Physical Chemistry B,
2013
13.
Nandi R., Amdursky N.
Accounts of Chemical Research,
2022
14.
Sülzner N., Hättig C.
Journal of Physical Chemistry A,
2022
15.
Wendler F., Sittig M., Tom J.C., Dietzek B., Schacher F.H.
Chemistry - A European Journal,
2020
16.
Liao S., Zhang X., Liu H., Chen Y., An D.
Synlett,
2022
17.
Cheng Y., Ma X., Zhai J., Xie X.
Chemical Communications,
2023
18.
Pode R.
Renewable and Sustainable Energy Reviews,
2020
19.
Badillo J.J., Saway J., Salem Z.M.
Synthesis,
2020
20.
Fakayode S.O., Lisse C., Medawala W., Brady P.N., Bwambok D.K., Anum D., Alonge T., Taylor M.E., Baker G.A., Mehari T.F., Rodriguez J.D., Elzey B., Siraj N., Macchi S., Le T., et. al.
Applied Spectroscopy Reviews,
2023
21.
Berton C., Pezzato C.
European Journal of Organic Chemistry,
2023
22.
Naumova A.O., Melnikov P.V., Kuzmin V.A., Zaitsev N.K.
Mendeleev Communications,
2023
23.
Ilyushchenko M.K., Salikov R.F., Sokolova A.D., Litvinenko V.V., Belyy A.Y., Platonov D.N., Tomilov Y.V.
Journal of Organic Chemistry,
2023
24.
Zhang J., Zhou M., Li X., Fan Y., Li J., Lu K., Wen H., Ren J.
Talanta,
2023
25.
Xu Q., Xiao F., Xu H.
TrAC - Trends in Analytical Chemistry,
2023
26.
Excited‐State Proton Transfer in Luminescent Dyes: From Theoretical Insight to Experimental Evidence
Fontes L.F., Rocha J., Silva A.M., Guieu S.
Chemistry - A European Journal,
2023
27.
Yang G., Li J., Deng X., Song X., Lu M., Zhu Y., Yu Z., Xu B., Li M., Dang L.
Journal of Physical Chemistry Letters,
2023
28.
Han G.R., Lim E., Kang J., Hwang D., Heo J., Kim S.K., Lee J.W.
Journal of Physical Chemistry A,
2023
29.
Xie J., Nealon R.E., Egan Z.T., Takematsu K.
Physical Chemistry Chemical Physics,
2023
30.
Sun T., Kang L., Zhao H., Zhao Y., Gu Y.
Advanced Science,
2023
31.
Pei H., Ye K., Shao Y., Chen D., Sun Z., Gong T., Liu D., Sun K.
Polymer Chemistry,
2024
32.
Sun P., Li Z., Zhang X., Liao Y., Liao S.
Macromolecular Rapid Communications,
2024
33.
Salikov R.F., Belyy A.Y., Ilyushchenko M.K., Platonov D.N., Sokolova A.D., Tomilov Y.V.
Chemistry - A European Journal,
2024
34.
Belyy A.Y., Sokolova A.D., Salikov R.F., Litvinenko V.V., Platonov D.N., Tomilov Y.V.
Mendeleev Communications,
2025