Keywords
fluorescence
molecular switches
phosphorus
porphyrin
protonation.
singlet oxygen
Abstract
Water-soluble phosphorus(v) porphyrin with p-amino- phenoxy groups as axial ligands was obtained, and its photophysical and photochemical properties were investigated and rationalized using quantum chemical calculations. It was demonstrated that at pH ≥ 6.1 this porphyrin did not emit or generate singlet oxygen, whereas at pH ≤ 2.0 it completely converted into the N-protonated form, which exhibited fluorescence and the ability to generate singlet oxygen.
References
.
Sh. Lebedeva N., Yurina E.S., Gubarev Y.A., Semeikin A.S., Syrbu S.A.
Mendeleev Communications,
2022
.
Popov A.S., Efimova A.A., Kazantsev A.V., Erzunov D.A., Lukashev N.V., Grozdova I.D., Melik-Nubarov N.S., Yaroslavov A.A.
Mendeleev Communications,
2021
.
Marenich A.V., Cramer C.J., Truhlar D.G.
Journal of Physical Chemistry B,
2009
.
Martynov A.G., Safonova E.A., Tsivadze A.Y., Gorbunova Y.G.
Coordination Chemistry Reviews,
2019
.
Martynov A.G., Mack J., May A.K., Nyokong T., Gorbunova Y.G., Tsivadze A.Y.
ACS Omega,
2019
.
Safonova E.A., Meshkov I.N., Polovkova M.A., Volostnykh M.V., Tsivadze A.Y., Gorbunova Y.G.
Mendeleev Communications,
2018
.
Meshkov I.N., Bulach V., Gorbunova Y.G., Gostev F.E., Nadtochenko V.A., Tsivadze A.Y., Hosseini M.W.
Chemical Communications,
2017
.
Meshkov I.N., Bulach V., Gorbunova Y.G., Kyritsakas N., Grigoriev M.S., Tsivadze A.Y., Hosseini M.W.
Inorganic Chemistry,
2016
.
Martynov A.G., Polovkova M.A., Berezhnoy G.S., Sinelshchikova A.A., Khrustalev V.N., Birin K.P., Kirakosyan G.A., Gorbunova Y.G., Tsivadze A.Y.
Inorganic Chemistry,
2021
.
Kolomeychuk F.M., Safonova E.A., Polovkova M.A., Sinelshchikova A.A., Martynov A.G., Shokurov A.V., Kirakosyan G.A., Efimov N.N., Tsivadze A.Y., Gorbunova Y.G.
Journal of the American Chemical Society,
2021
.
Gouterman M., Wagnière G.H., Snyder L.C.
Journal of Molecular Spectroscopy,
1963
.
Lochman L., Svec J., Roh J., Kirakci K., Lang K., Zimcik P., Novakova V.
Chemistry - A European Journal,
2016
.
Bannwarth C., Grimme S.
Computational and Theoretical Chemistry,
2014
.
Sauvage J.
Angewandte Chemie - International Edition,
2017
.
Mechanically Interlocked Molecules (MIMs)-Molecular Shuttles, Switches, and Machines (Nobel Lecture)
Stoddart J.F.
Angewandte Chemie - International Edition,
2017
.
Feringa B.L.
Angewandte Chemie - International Edition,
2017
.
Zhang J.L., Zhong J.Q., Lin J.D., Hu W.P., Wu K., Xu G.Q., Wee A.T., Chen W.
Chemical Society Reviews,
2015
.
Hirakawa K., Segawa H.
Journal of Photochemistry and Photobiology A: Chemistry,
1999
.
Fujitsuka M., Cho D.W., Tojo S., Inoue A., Shiragami T., Yasuda M., Majima T.
Journal of Physical Chemistry A,
2007
.
Akiba K., Nadano R., Satoh W., Yamamoto Y., Nagase S., Ou Z., Tan X., Kadish K.M.
Inorganic Chemistry,
2001
.
Canary J.W.
Chemical Society Reviews,
2009
.
Kolesnikov I.E., Kurochkin M.A., Meshkov I.N., Akasov R.A., Kalinichev A.A., Kolesnikov E.Y., Gorbunova Y.G., Lähderanta E.
Materials and Design,
2021
.
Natali M., Giordani S.
Chemical Society Reviews,
2012
.
Wong R.C., Lo P., Ng D.K.
Coordination Chemistry Reviews,
2019
.
Fei Q., Wang C., Wang B., Xu H., Li G., Huan Y., Shan H., Feng G.
Chemical Research in Chinese Universities,
2014
.
Grimme S., Hansen A., Ehlert S., Mewes J.
Journal of Chemical Physics,
2021
.
Kolesnikov I.E., Kalinichev A.A., Solomatina A.I., Kurochkin M.A., Meshkov I.N., Kolesnikov E.Y., Gorbunova Y.G.
Sensors and Actuators, A: Physical,
2022
.
Martynov A.G., Polovkova M.A., Gorbunova Y.G., Tsivadze A.Y.
Molecules,
2022
.
Wellm V., Näther C., Herges R.
Journal of Organic Chemistry,
2021
.
Furuyama T., Okujima T., Muramatsu K., Takahashi Y., Mikami A., Fukumura T., Mori S., Nakae T., Takase M., Uno H., Kobayashi N.
European Journal of Organic Chemistry,
2019
.
Norvaiša K., Kielmann M., Senge M.O.
ChemBioChem,
2020
.
Benny R., Sahoo D., George A., De S.
ChemistryOpen,
2022
.
Zhan Y., Cao K., Wang C., Jia J., Xue P., Liu X., Duan X., Lu R.
Organic and Biomolecular Chemistry,
2012
.
Norel L., Tourbillon C., Warnan J., Audibert J., Pellegrin Y., Miomandre F., Odobel F., Rigaut S.
Dalton Transactions,
2018
.
Zheng B., Huang Z., Lv L., Lan W., Hu J., Li X., Zheng B., Ke M., Huang J.
Journal of Materials Chemistry B,
2021
.
Barbour T., Belcher W.J., Brothers P.J., Rickard C.E., Ware D.C.
Inorganic Chemistry,
1992
.
Cardoso D., Perucha E.
Clinical Science,
2021
.
Fang D., Zhu J.
Cellular and Molecular Life Sciences,
2019
.
Safonova E., Kolomeychuk F., Gvozdev D., Tsivadze A., Gorbunova Y.
Molecules,
2023
.
Hirakawa K., Segawa H.
Journal of Photochemistry and Photobiology A: Chemistry,
2010
.
Guerchais V., Ordronneau L., Le Bozec H.
Coordination Chemistry Reviews,
2010
.
Hirakawa K., Azumi K., Nishimura Y., Arai T., Nosaka Y., Okazaki S.
Journal of Porphyrins and Phthalocyanines,
2012
.
Furuyama T., Takahashi Y., Fukumura T., Bacilla A.C., Kobayashi N.
Journal of Porphyrins and Phthalocyanines,
2019
.
Li D., Cai S., Wang P., Cheng H., Cheng B., Zhang Y., Liu G.
Advanced healthcare materials,
2023
.
Batishchev O.V., Kalutskii M.A., Varlamova E.A., Konstantinova A.N., Makrinsky K.I., Ermakov Y.A., Meshkov I.N., Sokolov V.S., Gorbunova Y.G.
Frontiers in Molecular Biosciences,
2023