Каталитические системы на основе комплексов кобальта с водо-растворимыми фталоцианинами

A. Вашурин,^a^,c^@ И. Кузьмин,^a M. Разумов,^a O. Голубчиков,^b O. Койфман^b

Посвящается профессору Олегу Александровичу Голубчикову по случаю его 70-летия

^aКафедра неорганической химии, Ивановский государственный химико-технологический университет, 153000 Иваново, Россия

^bИнститут химии макрогетероциклов, Ивановский государственный химико-технологический университет, 153000 Иваново, Россия

^cКазанский Федеральный Университет, 420008 Казань, Россия

^@E-mail: asvashurin@mail.ru

DOI: 10.6060/mhc180168v

Макрогетероциклы 2018 11(1) 11-20

В работе приводится краткое обобщение каталитических свойств для ряда сульфированных производных фталоцианината кобальта, имеющих закономерно изменяющиеся по структуре периферические заместители. Приводятся сведения о гетерогенизации фталоцианинатов кобальта в органические и неорганические полимеры. Проводится сравнение каталитической активности макроциклов в зависимости от структуры их периферического заместителя и типа полимерного носителя. Показана перспектива применения сульфокислот фталоцианината кобальта в тонком органическом синтезе тиурама Е, как в гомогенном, так и гетерогенном катализе.

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References:

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1. Kadish K.,‎ Guilard R.,‎ Smith K. Phthalocyanines: Synthesis. In: The Porphyrin Handbook, V.15 Academic Press, 2002. 369 p.

2. Lukyanets E.A., Nemykin V.N. J. Porphyrins Phthalocyanines 2010, 14, 1–40.
https://doi.org/10.1142/S1088424610001799

3. Tuncer S., Kaya K., Özçeşmeci İ., Burat A. J. Organomet. Chem. 2017, 827, 78–85.
https://doi.org/10.1016/j.jorganchem.2016.11.008

4. Çakır V., Göksel M., Durmuş M., Biyiklioglu Z. Dyes Pigm. 2016, 125, 414–425.
https://doi.org/10.1016/j.dyepig.2015.10.035

5. Bekaroğlu Ö. J. Porphyrins Phthalocyanines 2000, 4, 465–473.
https://doi.org/10.1002/1099-1409(200008)4:5<465::AID-JPP263>3.0.CO;2-3

6. Furuyama T., Satoh K., Kushiya T., Kobayashi N. J. Am. Chem. Soc. 2014, 136, 765–776.
https://doi.org/10.1021/ja411016f

7. Hanack M., Iqbal Z., Lyubimtsev A., Özcesmeci I., Özcesmeci M., Ziegler T. J. Porphyrins Phthalocyanines 2009, 13, 312–321.
https://doi.org/10.1142/S1088424609000395

8. Kulinich V., Shaposhnikov G., Badaukaite R. Macroheterocycles 2010, 3, 23–29.
https://doi.org/10.6060/mhc2010.1.23

9. Ali H., Lier J. Tetrahedron Lett. 2014, 55, 4163–4167.
https://doi.org/10.1016/j.tetlet.2014.05.053

10. Toriumi N., Muranaka A., Hashizume D., Uchiyama M. Tetrahedron Lett. 2017, 58, 2267–2271.
https://doi.org/10.1016/j.tetlet.2017.04.089

11. Karaoğlan G., Gümrükçü G., Gördük S., Can N., Gül A. Synth. Met. 2017, 230, 7–11.
https://doi.org/10.1016/j.synthmet.2017.04.019

12. Martynov A., Zubareva O., Gorbunova Y., Sakharov S., Tsivadze A. Inorg. Chim. Acta 2009, 362, 11–18.
https://doi.org/10.1016/j.ica.2008.01.008

13. Ikeue T., Sonoda M., Kurahashi S., Tachibana H., Teraoka D., Sugimori T., Kasuga K., Handa M. Inorg. Chem. Commun. 2010, 13, 1170–1172.
https://doi.org/10.1016/j.inoche.2010.06.041

14. Ikeue T., Sawada N., Matsumoto N., Miyazaki A., Sugimori T., Koikawa M., Hiromitsu I., Yoshino K., Mikuriya M., Kataoka Y., Handa M. J. Porphyrins Phthalocyanines 2014, 18, 708–714.
https://doi.org/10.1142/S1088424614500485

15. Quartarolo A., Pérusse D., Dumoulin F., Russo N., Sicilia E. J. Porphyrins Phthalocyanines 2017, 17, 980–988.
https://doi.org/10.1142/S1088424613500569

16. Makarov S., Suvorova O., Wöhrle D. J. Porphyrins Phthalocyanines 2011, 15, 791–808.
https://doi.org/10.1142/S1088424611003835

17. Ali H., Baillargeon P., Lier J. Tetrahedron Lett. 2008, 49, 7253–7255.
https://doi.org/10.1016/j.tetlet.2008.09.160

18. Bizet F., Ipuy M., Bernhard Y., Lioret V., Winckler P., Goze C., Perrier-Cornet J., Decréau R. Bioorg. Med. Chem. 2018, 26, 413–420.
https://doi.org/10.1016/j.bmc.2017.11.050

19. Yanık H., Göksel M., Yeşilot S., Durmuş M. Tetrahedron Lett. 2016, 57, 2922–2926.
https://doi.org/10.1016/j.tetlet.2016.05.080

20. Li K., Qiu L., Liu Q., Lv G., Zhao X., Wang S., Lin J. J. Photochem. Photobiol., B 2017, 174, 243–250.
https://doi.org/10.1016/j.jphotobiol.2017.08.003

21. Birin K., Chugunov V., Krapivenko A., Gorbunova Y., Tsivadze A. Macroheterocycles 2014, 7, 153–161.
https://doi.org/10.6060/mhc140508b

22. Geis C., Schneider S., Schlettwein D. J. Porphyrins Phthalocyanines 2016, 20, 1166–1172.
https://doi.org/10.1142/S1088424616500826

23. Sawada K., Duan W., Sekitani K., Satoh K. J. Mol. Liq. 2005, 119, 171–176.
https://doi.org/10.1016/j.molliq.2004.10.029

24. Bilgin A., Yağcı Ç. Eur. Polymer J. 2014, 61, 240–252.
https://doi.org/10.1016/j.eurpolymj.2014.10.009

25. Torre G., Torres T. J. Porphyrins Phthalocyanines 2002, 6, 274–284.
https://doi.org/10.1142/S1088424602000324

26. Chakraborty J. Fundamentals and practices in colouration of textiles. WPI Publishing, 2014. р. 169.

27. Dao Q., Hori T., Fukumura K., Masuda T., Kamikado T., Fujii A., Shimizu Y., Ozaki M. Org. Electron. 2013, 14, 2628–2634.
https://doi.org/10.1016/j.orgel.2013.05.041

28. Huang H., Cao Z., Li X., Zhang L., Liu X., Zhao H., Tan S. Synth. Met. 2012, 162, 2316–2321.
https://doi.org/10.1016/j.synthmet.2012.11.007

29. Wang K., Qi D., Li Y., Wang T., Liu H., Jiang J. Coord. Chem. Rev. 2017, doi: 10.1016/j.ccr.2017.08.023.
https://doi.org/10.1016/j.ccr.2017.08.023

30. Zvyagina A., Shiryaev A., Baranchikov A., Chernyshev V., Enakieva Y., Raitman O., Ezhov A., Meshkov I., Grishanov D., Ivanova O., Gorbunova Y., Arslanova V., Kalinina M. New J. Chem. 2017, 41, 948–957.
https://doi.org/10.1039/C6NJ03202H

31. Kobayashi N. Coord. Chem. Rev. 2001, 219-221, 99–123.
https://doi.org/10.1016/S0010-8545(01)00323-X

32. Safonova E., Martynov A., Nefedov S., Kirakosyan G., Gorbunova Y., Tsivadze A. Inorg. Chem. 2016, 55, 2450–2459.
https://doi.org/10.1021/acs.inorgchem.5b02831

33. Oluwole D., Yagodin A., Mkhize N., Sekhosana K., Martynov A., Gorbunova Y., Tsivadze A., Nyokong T. Chem. Eur. J. 2017, 23, 2820–2830.
https://doi.org/10.1002/chem.201604401

34. Li Z., Gao F., Xiao Z., Wu X., Zuo J., Song Y. Optics Laser Technol. 2018, 103, 42–47.
https://doi.org/10.1016/j.optlastec.2018.01.011

35. Zhao P., Wang Z., Chen J., Zhou Y., Zhang F. Opt. Mater. 2017, 66, 98–105.
https://doi.org/10.1016/j.optmat.2017.01.029

36. Tamura R., Kawata T., Hattori Y., Kobayashi N., Kimura M. Macromol. 2017, 50, 7978–7983.
https://doi.org/10.1021/acs.macromol.7b01713

37. Sorokin A. Chem. Rev. 2013, 113, 8152–8191.
https://doi.org/10.1021/cr4000072

38. Zhou W., Zhou J., Chen Y., Cui A., Sun F., He M., Xu Z., Chen Q. Appl. Catal., A 2017, 542, 191–200.
https://doi.org/10.1016/j.apcata.2017.05.029

39. Gao Y., Chen L., Quan M., Zhang G., Zheng Y., Zhao J. J. Electroanal. Chem. 2018, 808, 8–13.
https://doi.org/10.1016/j.jelechem.2017.11.062

40. Luo R., Lin X., Lu J., Zhou X., Ji H. Chin. J. Catal. 2017, 38, 1382–1389.
https://doi.org/10.1016/S1872-2067(17)62877-8

41. Chauhan D., Kumar P., Painuly R., Kumar S., Jain S., Ganguly S. Fuel Process. Technol. 2017, 162, 135–146.
https://doi.org/10.1016/j.fuproc.2017.04.003

42. Bricker J., Laricchia L. Top. Catal. 2012, 55, 1315–1323.
https://doi.org/10.1007/s11244-012-9913-0

43. Nemykin V., Polshyna A., Borisenkova S., Strelko V. J. Mol. Catal. A: Chem. 2007, 264, 103–109.
https://doi.org/10.1016/j.molcata.2006.08.093

44. Goifman A., Guna J., Gitisa V., Kamyshny A., Leva J. Appl. Catal., B 2004, 54, 225–235.
https://doi.org/10.1016/j.apcatb.2004.07.003

45. Hassanein M., Gerges S., Abdo M., El-Khalafy S. J. Mol. Catal. A: Chem. 2005, 240, 22–26.
https://doi.org/10.1016/j.molcata.2005.05.043

46. Ochoa G., Gutierrez C., Ponce I., Paez M., Pavez J., Zagal J., Silva J.F. J. Electroanal. Chem. 2010, 639, 88–94.
https://doi.org/10.1016/j.jelechem.2009.11.027

47. Kimura M., Yamaguchi Y., Koyama T. J. Porphyrins Phthalocyanines 1997, 1, 309–313.
https://doi.org/10.1002/(SICI)1099-1409(199710)1:4<309::AID-JPP36>3.0.CO;2-R

48. Weissberger A., Proskauer E., Riddick J., Toops E. Organic solvent: physical properties and methods of purification. New York: Publishers Inc., 1955. 447 p.

49. Karyakin Yu., Angelov I. Pure chemicals reagents. Moscow: Chemistry, 1974. 408 p. (in Russ.)

50. Weber J., Busch D. Inorg. Chem. 1965, 4, 472–475.
https://doi.org/10.1021/ic50026a008

51. Voronina A., Kuzmin I., Vashurin A., Shaposhnikov G., Pukhovskaya S., Golubchikov O. Russ. J. Gen. Chem. 2014, 84, 1777–1781.
https://doi.org/10.1134/S1070363214090230

52. Vashurin A., Filippova A., Znoyko S., Voronina A., Lefedova O., Kuzmin I., Maizlish V. J. Porphyrins Phthalocyanines 2015, 19, 983–996.
https://doi.org/10.1142/S1088424615500753

53. Vashurin A., Kuzmin I., Razumov M., Pukhovskaya S., Golubchikov O., Voronina A., Shaposhnikov G., Koifman O. J. Porphyrins Phthalocyanines 2015, 19, 1–9.
https://doi.org/10.1142/S1088424614501016

54. Filippova A., Vashurin A., Znoyko S., Kuzmin I., Razumov M., Chernova A., Shaposhnikov G., Koifman O. J. Mol. Struct. 2017, 1149, 17–26.
https://doi.org/10.1016/j.molstruc.2017.07.086

55. Snow A. Phthalocyanines: Properties and Materials. In: The Porphyrin Handbook, V. 17, Academic Press, 2003. p. 129–176.

56. Vashurin A., Kuzmin I., Litova N., Petrov O., Pukhovskaya S., Golubchikov O. Russ. J. Phys. Chem. 2014, 88, 2064–2067.
https://doi.org/10.1134/S0036024414120395

57. Vashurin A., Maizlish V., Kuzmin I., Petrov O., Razumov M., Pukhovskaya S., Golubchikov O., Koifman O. J. Incl. Phenom. Macrocycl. Chem. 2016, 87, 37–43.
https://doi.org/10.1007/s10847-016-0674-4

58. Vashurin A. Russ. Chem. Bull. 2016, 65, 2220–2228.
https://doi.org/10.1007/s11172-016-1572-z

59. Vashurin A., Pukhovskaya S., Semeikin A., Golubchikov O. Macroheterocycles 2012, 5, 72–75.
https://doi.org/10.6060/mhc2012.111251v

60. Chandra B.KC, D'Souza F. Coord. Chem. Rev. 2016, 322, 104–141.
https://doi.org/10.1016/j.ccr.2016.05.012

61. Vashurin A., Voronina-Chernova A., Maizlish V., Koifman O. Mendeleev Commun. 2017, 27, 16–18.
https://doi.org/10.1016/j.mencom.2017.01.004

62. Tyapochkin E., Kozliak E. J. Mol. Catal. 2005, 242, 1–17.
https://doi.org/10.1016/j.molcata.2005.07.008

63. Vashurin A., Maizlish V., Pukhovskaya S., Voronina A., Kuzmin I., Futerman A., Golubchikov O., Koifman O. J. Porphyrins Phthalocyanines 2015, 19, 573–581.
https://doi.org/10.1142/S1088424614501028

64. Vashurin A., Kuzmin I., Mayzlish V., Razumov M., Golubchikov O., Koifman O. J. Serb. Chem. Soc. 2016, 81, 1025–1036.
https://doi.org/10.2298/JSC160105048V

65. Kaliya O.L., Lukyanets E.A., Vorozhtsov G.N. J. Porphyrins Phthalocyanines 1999, 3, 592–610.
https://doi.org/10.1002/(SICI)1099-1409(199908/10)3:6/7<592::AID-JPP180>3.0.CO;2-G

66. Anisimov A.V., Mohammed R.A., Borisenkova S.A., Tarakanova A.V., Barkanova S.V., Derkacheva V.M., Negrimovskii V.M., Kaliya O.L., Lukyanets E.A. Petrol. Chem. 1994, 34, 347–352.

67. Costa A., Ghesti G., de Macedo J., Braga V., Santos M., Dias J., Dias S. J. Mol. Catal. 2008, 282, 149–157.
https://doi.org/10.1016/j.molcata.2007.12.024

68. Altın İ., Sökmen M., Bıyıklıoğlu Z. Mater. Sci. Semicond. Process. 2016, 45, 36–44.
https://doi.org/10.1016/j.mssp.2016.01.016

69. Li P., Ding Y., Wang A., Zhou L., Wei S., Zhou Y., Tang Y., Chen Y., Cai C., Lu T. ACS Appl. Mater. Interfaces 2013, 5, 2255–2260.
https://doi.org/10.1021/am400152k

70. Bazarnik M., Brede J., Decker R., Wiesendanger R. ACS Nano 2013, 7, 11341–11349.
https://doi.org/10.1021/nn405172q

71. Gol'dshleger N., Baulin V., Tsivadze A. Prot. Metals Phys. Chem. Surf. 2014, 50, 135–172.
https://doi.org/10.1134/S2070205114020087

72. Hongbing Zh., Wenzhe Ch., Jianchun Ch., Minquan W. Mater. Sci. Eng., B 2003, 100, 119–123.
https://doi.org/10.1016/S0921-5107(03)00085-0

73. Hongbing Zh., Wenzhe Ch., Minquan W. Mater. Lett. 2003, 57, 1108–1112.
https://doi.org/10.1016/S0167-577X(02)00939-4

74. Kuznetsova N., Kaliya O. Macroheterocycles 2015, 8, 8–19.
https://doi.org/10.6060/mhc141243k

75. Morandeira A., López-Duarte I., Martínez-Díaz M., O'Regan B., Shuttle C., Haji-Zainulabidin N., Torres T., Palomares E., Durrant J. J. Am. Chem. Soc. 2007, 129, 9250–9251.
https://doi.org/10.1021/ja0722980

76. Fashina A., Antunes E., Nyokong T. Polyhedron 2013, 53, 278–285.
https://doi.org/10.1016/j.poly.2013.01.037

77. Zuev K., Perevalov V., Vinokurov E., Zhigunov F., Koldaeva T. Macroheterocycles 2016, 9, 250–256.
https://doi.org/10.6060/mhc160212z

78. Ezhov A., Zhdanova K., Bragina N., Mironov A. Macroheterocycles 2016, 9, 337–352.
https://doi.org/10.6060/mhc160752e

79. Makhseed S., Al-Kharafi F., Samuel J., Ateya B. Catal. Commun. 2009, 10, 1284–1287.
https://doi.org/10.1016/j.catcom.2009.01.034

80. Akopyants Y.G., Borisenkova S.A. J. Mol. Catal. 1993, 83, 1–16.
https://doi.org/10.1016/0304-5102(93)87003-Q

81. Synak A., Gil M., Organero J., Sánchez F., Iglesias M., Douhal A. J. Phys. Chem. C 2009, 113, 19199–19207.
https://doi.org/10.1021/jp9021129

82. Zhao Z., Fan J., Wang Z. J. Cleaner Product. 2007, 15, 1894–1897.
https://doi.org/10.1016/j.jclepro.2006.05.003

83. Marfin Y., Vashurin A., Rumyantsev E., Puhovskaya S. J. Sol-Gel Sci. Technol. 2013, 66, 306–311.
https://doi.org/10.1007/s10971-013-3009-6

84. Voronina A., Tarasyuk I., Marfin Y., Vashurin A., Rumyantsev E., Pukhovskaya S. J. Non-Cryst. Solids 2014, 406, 5–10.
https://doi.org/10.1016/j.jnoncrysol.2014.09.009

85. Tarasyuk I., Kuzmin I., Marfin Y., Vashurin A., Voronina A., Rumyantsev E. Synth. Met. 2016, 217, 189–196.
https://doi.org/10.1016/j.synthmet.2016.03.037

86. Fisher H., Schulz-Ekloff G., Wöhrle D. Chem. Eng. Technol. 1997, 20, 624–632.
https://doi.org/10.1002/ceat.270200909

87. Hoffmann M., Hong A. Sci. Total Environ. 1987, 64, 99–115.
https://doi.org/10.1016/0048-9697(87)90125-2

88. Borisenkova S. Petrol. Chem. 1991, 31, 391–408.

89. Schutten J., Beelen T. J. Mol. Catal. 1981, 10, 85.
https://doi.org/10.1016/0304-5102(80)80052-6

90. Wohrle D., Buck T., Schneider G., Schulz-Ekloff G., Fischer H. J. Inorg. Organomet. Polym. 1991б 1б 115-130.
https://doi.org/10.1007/BF00701033

91. van Welzen J., van Herk A., German A. Macromol. Chem. Phys. 1987, 188, 1923.
https://doi.org/10.1002/macp.1987.021880815

92. Surdhar P., Armstrong D. J. Phys. Chem. 1986, 90, 5915.
https://doi.org/10.1021/j100280a091

93. Surdhar P., Armstrong D. J. Phys. Chem. 1987, 91, 6532.
https://doi.org/10.1021/j100310a022

94. Berezin B., Koifman O. Russ. Chem. Rev. 1980, 49, 2389–2417.
https://doi.org/10.1070/RC1980v049n12ABEH002537

95. Vashurin A., Marfin Yu., Kuzmin I. Znoyko S., Rumyantsev E. J. Sol-Gel Sci. Technol. 2018.

96. Makino M., Aihara J. J. Phys. Chem. A. 2012, 116, 8074–8084.
https://doi.org/10.1021/jp304681h

97. Chatti I., Chorbel A., Grange P., Colin J. Catal. Today 2002, 75, 113–117.
https://doi.org/10.1016/S0920-5861(02)00051-2

98. Liu H., Min E. Green Chem. 2006, 8, 6572.

99. Rayati S., Chegini E. Macroheterocycles 2016, 9, 151–155.
https://doi.org/10.6060/mhc151101r

100. Rashidi A., Mirzaeian M., Khodabakhshi S. J. Nat. Gas Sci. Eng. 2015, 25, 103–109.
https://doi.org/10.1016/j.jngse.2015.04.037

101. Vashurin A., Kuzmin I., Titov V., Pukhovskaya S., Razumov M., Golubchikov O., Koifman O. Macroheterocycles 2015, 8, 351–357.
https://doi.org/10.6060/mhc150248v

102. Joseph J., Jain S., Sain B. Ind. Eng. Chem. Res. 2010, 49, 6674–6677.
https://doi.org/10.1021/ie100351s

103. Felix T., Trigueiro J., Bundaleski N., Teodoro O.M.N.D., Sério S., Debachera N. Appl. Surf. Sci. 2018, 428, 730–738.
https://doi.org/10.1016/j.apsusc.2017.09.147

104. Zaitsev A., Lacoste A., Poncin-Epaillard F., Bès A., Debarnot D. Surf. Coat. Technol. 2017, 330, 196–203.
https://doi.org/10.1016/j.surfcoat.2017.10.010

105. Vashurin A.S., Badaukaite R.A., Futerman N.A., Pukhovskaya S.G., Shaposhnikov G.P., Golubchikov O.A. Petrol. Chem. 2013, 53, 197–200.
https://doi.org/10.1134/S0965544113030122

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Каталитические системы на основе комплексов кобальта с водо-растворимыми фталоцианинами

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