Новый 4-Карбоксифенилзамещенный порфиразин, его эфир и их комплексы с Zn(II)

  • Svetlana S. Ivanova Ivanovo State University of Chemistry and Technology
  • Denis S. Salnikov
  • Ekaterina D. Rychikhina Ivanovo State University of Chemistry and Technology
  • Pavel A. Stuzhin

Аннотация

The porphyrazines bearing eight 4-carboxyphenyl and 4-butoxycarbonylphenyl groups (H2Pz(PhCOOH)8 and H2Pz(PhCOOBu)8), as well as their Zn(II) complexes were obtained and characterized by spectral methods. The conversion of carboxyl derivatives into their anionic forms H2Pz(PhCOO-)8 and ZnPz(PhCOO-)8 in the presence of alkali leads to water-soluble species. ZnPz(PhCOOH)8 and ZnPz(PhCOOBu)8 possess the high ability to generate singlet oxygen in DMF solutions (ФΔ = 80-83%), while their metal free analogues are weak photosensitizers due to their aggregation tendency.

Литература

. Wöhrle D., Schnurpfeil G., Makarov S.G., Kazarin A., Suvorova O.N. Macroheterocycles 2012, 5, 191-202. https://doi.org/10.6060/mhc2012.120990w

Lukyanets E.A. J. Porphyrins Phthalocyanines 1999, 3, 424-432. https://doi.org/10.1002/(SICI)1099-1409(199908/10)3:6/7<424::AID-JPP151>3.3.CO;2-B

Dumoulin F., Durmus M., Ahsen V., Nyokong T. Coord. Chem. Rev. 2010, 254, 2792-2847. https://doi.org/10.1016/j.ccr.2010.05.002

Kuznetsova N.A., Shevchenko E.N., Makarov D.A., Slivka L.K., Solovyova L.I., Kaliya O.L., Lukyanets E.A. J. Porphyrins Phthalocyanines 2012, 16, 1244-1251. https://doi.org/10.1142/S1088424612501301

Kaliya O.L., Kuznetsova N.A., Bulgakov R.A., Solovyova L.I., Shevchenko E.N., Slivka L.K., Lukyanets E.A. Macroheterocycles 2016, 9, 186-192. https://doi.org/10.6060/mhc160646k

Kuznetsova N.A., Bulgakov R.A., Solovyova L.I., Shevchenko E.N., Kaliya O.L., Lukyanets E.A. Macroheterocycles 2015, 8, 143-149. https://doi.org/10.6060/mhc150353k

Kuznetsova N.A., Fedorova T.M., Solovyova L.I., Shevchenko E.N., Bordaev E.B., Bulgakov R.A., Kaliya O.L., Lukyanets E.A. Macroheterocycles 2018, 11, 21-28. https://doi.org/10.6060/mhc171152k

Zhang Y., Tian M., Majeed Z., Xie Y., Zheng K., Luo Z., Li C., Zhao C. Separations 2023, 10, 196. https://doi.org/10.3390/separations10030196

Gorbunova Yu.G., Enakieva Yu.Yu., Volostnykh M.V., Sinelshchikova A.A., et al. Russ. Chem. Rev. 2022, 91(4), RCR5038. https://doi.org/10.1070/RCR5038

Han B., Ding X., Yu B., Wu H., Zhou W., Liu W., Wei Ch., Chen B., Qi D., Wang H., Wang K., Chen Y., Chen B., Jiang J. J. Am. Chem. Soc. 2021, 143, 7104−7113. https://doi.org/10.1021/jacs.1c02145

Opris D.M., Nuesch F., Lowe Ch., Molberg M., Nagel M. Chem. Mater. 2008, 20, 6889-6896. https://doi.org/10.1021/cm801871t

Kudrevich S.V., Galpern M.G., van Lier J.E. Synthesis 1994, 08, 779-781. https://doi.org/10.1055/s-1994-25571

Yagodin A.V., Mikheev I.A., Dolgushin F.M., Martynov A.G., Gorbunova Yu.G., Tsivadze A.Yu. Macroheterocycles 2023, 16, 218-224. https://doi.org/10.6060/mhc235129m

Yagodin A.V., Mikheev I.A., Bunin D.A., Sinelshchikova A.A., Martynov A.G., Gorbunova Yu.G., Tsivadze A.Yu. Dyes Pigm. 2023, 216, 111326. https://doi.org/10.1016/j.dyepig.2023.111326

Sakellariou E.G., Montalman A.G., Beall S.L., Henderson D., Meunier H.G., Phillips D., Suhling K., Barrett A.G.M., Hoffman B.M. Tetrahedron 2003, 59, 9083-9090. https://doi.org/10.1016/j.tet.2003.09.060

Seybold P.G., Gouterman M. J. Mol. Spectrosc. 1969, 31, 1-6. https://doi.org/10.1016/0022-2852(69)90335-X

Spiller W., Kliesch H., Wöhrle D., Hackbarth S., Röder B., Schnurpfeil G. J. Porphyrins Phthalocyanines 1998, 2, 145-158. https://doi.org/10.1002/(SICI)1099-1409(199803/04)2:2<145::AID-JPP60>3.0.CO;2-2

a) Bulgakov R.A., Kuznetsova N.A., Dolotova O.V., Solovieva L.I., Mack J., Chidawanyika Wadzanai J.U., Kaliya O.L., Nyokong T. J. Porphyrins Phthalocyanines 2012, 16, 1217-1224. https://doi.org/10.1142/S1088424612501209

b) Pat. RF 2193563, 2000.

Ivanova S.S., Salnikov D.S., Knorr G., Ledovich O., Sliznev V., Kubat P., Novakova V., Stuzhin P.A. Dalton Trans. 2022, 51, 1364-1377. https://doi.org/10.1039/D1DT02453A

Опубликован
2023-12-19
Как цитировать
Ivanova, S., Salnikov, D., Rychikhina, E., & Stuzhin, P. (2023). Новый 4-Карбоксифенилзамещенный порфиразин, его эфир и их комплексы с Zn(II). Макрогетероциклы/Macroheterocycles, 16(4), 287-290. https://doi.org/10.6060/mhc235568i
Раздел
Порфиразины