Electrochemical Characterization of β-Alkyl Substituted Porphyrins and Mn(III) Complexes in Alkaline Solution

Nadezhda M. Berezina,^a^@ Maria E. Klueva,^b and Mikhail I. Bazanov^a

^aIvanovo State University of Chemistry and Technology, Research Institute of Macroheterocyclic Compounds,
153000 Ivanovo, Russia

^bIvanovo State Medical Academy of the Ministry of Healthcare of the Russian Federation, 153000 Ivanovo, Russia

^@Corresponding author E-mail: sky_berezina@rambler.ru

DOI: 10.6060/mhc170507b

Macroheterocycles 2017 10(3) 308-312

A comparative study of electrochemical and electrocatalytic properties of 3,7,12,18-tetramethyl-2,8,13,17-tetraethylporphine (H₂TMeTEtP, Etio IV), 2,3,7,8,12,13,17,18-octaethylporphyrin (H₂OEtP) and their complexes ((Cl)MTMeTEtP, (Cl)MOEtP, M=Mn(III)) was conducted by cyclic voltammetry in 0.1 M KOH. The sequence and areas of electrochemical processes were established. Values of the half-wave potentials of the first and second electroreduction processes of the π-electron macrocycle system as a whole were correlated with the increase in the length of alkyl substituents. The positive effect of increasing length of a functional substituent at β-positions in a porphine molecule on the electrocatalytic activity of the compounds in the oxygen reduction reaction (ORR) was established.

References:

Click here to expand or collapse this section

1. Shaposhnikov G.P., Kulinich V.P., Maizlish V.E. Modified Phthalocyanines and their Structural Analogues (Koifman O.I., Ed.), M.: Krasand, 2012. 480 p. (In Russ.). [Шапошников Г.П., Кулинич В.П., Майзлиш В.Е. Модифицированные фталоцианины и их структурные аналоги (Койфман О.И., ред.) М.: Красанд, 2012. 480 с.]

2. Felton R.H. The Porphyrins. (Dolphin D., Ed.) New York: Academic Press, 1978. Chapter 3.

3. Fuhrhop J.-H. Porphyrins and Metalloporphyrins. (Smith K., Ed.) New York: Elsevier, 1975. Chapter 14.

4. Kadish K.M., Cornillon J.-L., Yao C.-L., Malinski T., Gritzner G. J. Electroanal. Chem. 1987, 235, 189–207.
https://doi.org/10.1016/0022-0728(87)85207-5

5. Van Caemelbecke E., Kutner W., Kadish K.M. Inorg. Chem. 1993, 23, 438–444.
https://doi.org/10.1021/ic00056a016

6. Autret M., Ou Z.P., Antonini A., Boschi T., Tagliatesta P., Kadish K.M. J. Chem. Soc., Dalton Trans. 1996, 2793–2797.
https://doi.org/10.1039/dt9960002793

7. Mu X.H., Schultsz F.A. Inorg. Chem. 1995, 34, 3835–3837.
https://doi.org/10.1021/ic00118a038

8. Meunier B. Chem. Rev. 1992, 92, 1411.
https://doi.org/10.1021/cr00014a008

9. Lee J., Hunt J.A., Groves J.T. J. Am. Chem. Soc. 1998, 120, 6053–6061.
https://doi.org/10.1021/ja9801036

10. Rodgers K.R., Goff H.M. J. Am. Chem. Soc. 1988, 110, 7049–7060.
https://doi.org/10.1021/ja00229a018

11. Kadish, K.M., Caemelbecke E.V., Royal G. Electrochemistry of Metalloporpyrins in Nonaqueous Media. In: The Porphyrin Handbook (Kadish K.M. et al., Eds.) San Diego: Academic Press, 2000. V. 8. Chapter 55. p. 1–114.

12. Arasassingham R.D., He G.-X., Bruice T.C. J. Am. Chem. Soc. 1993, 115, 7985–7991.
https://doi.org/10.1021/ja00071a008

13. Collins T.J., Powell R.D., Slebodnick C., Uffelman E.S. J. Am. Chem. Soc. 1990, 112, 899–901.
https://doi.org/10.1021/ja00158a077

14. Arasassingham R.D., Bruice T.C. Formation and Alkene Epoxidation by Higher-Valent Oxo-Metalloporphyrins. (Barton D.H.R., Ed.) New York: Plenum Press, 1993.
https://doi.org/10.1007/978-1-4615-3000-8_12

15. Groves J.T., Stern M.K. J. Am. Chem. Soc. 1988, 110, 8628–8638.
https://doi.org/10.1021/ja00234a009

16. Camenzind M.J., Hollander F.J., Hill C.L. Inorg. Chem. 1982, 21, 4301–4308.
https://doi.org/10.1021/ic00142a036

17. Hill C.L., Hollander F.J. J. Am. Chem. Soc. 1982, 104, 7318–7319.
https://doi.org/10.1021/ja00389a072

18. Schardt B.C., Hollander F., Hill C.L. J. Chem. Soc., Chem. Commun. 1982, 104, 3964–3972.
https://doi.org/10.1021/ja00378a032

19. Buchler J.W., Dreher C., Lay K.-L., Lee Y.J.A., Scheidt W.R. Inorg. Chem. 1983, 22, 888–891.
https://doi.org/10.1021/ic00148a010

20. Bottomly L.A., Neely F.L. J. Am. Chem. Soc. 1989, 111, 5955–5957.
https://doi.org/10.1021/ja00197a074

21. Klueva M.E., Lomova T.N. Mendeleev Commun. 2002, 2(8), 238–239.
https://doi.org/10.1070/MC2002v012n06ABEH001656

22. Do Ngoc Minh, Berezina N.M., Bazanov M.I., Semeikin A.S., Glazunov A.V. Macroheterocycles 2015, 8, 56–64.
https://doi.org/10.6060/mhc140714b

23. Antipin I.S., Antina E.V., Bazanov M.I. etc. In: Advances in Porphyrin Chemistry (Golubchikov O.A., Ed.) StPSU: NII Khimii, 2007, Vol. 5, pp. 273–291 (in Russ.) [Антипин И.С., Антина Е.В., Базанов М.И. и др. В кн.: Успехи химии порфиринов (Голубчиков О.А., ред.), СПбГУ: НИИ Химии, 2007. Т. 5. c. 273–291].

24. Koca A., Dincer H.A., Kocak M.B., Gui A. Russ. J. Electrochem. 2006, 42(1), 31–37.
https://doi.org/10.1134/S102319350601006X

25. Kuzmin S.M., Chulovskaya S.A., Parfenyuk V.I. J. Porphyrins Phthalocyanines 2015, 19, 1053–1062.

https://doi.org/10.1142/S1088424615500807

Attachment	Size
mhc170507b.pdf	854.59 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Electrochemical Characterization of β-Alkyl Substituted Porphyrins and Mn(III) Complexes in Alkaline Solution

References: