Порфирины p-Металлов: от Специфичности Свойств к Применению в Медицине, Катализе и Оптоэлектронике
Аннотация
Статья представляет собой краткий обзор последних работ в области физической и прикладной химии порфириновых комплексов элементов главных подгрупп. В обсуждение включены несколько классических статей по этой теме. Особое внимание уделяется специфике методов получения, с демонстрацией конкретных оригинальных синтезов, а также оптических свойств, реакционной способности и новых применений. Кратко представлены перспективы использования порфириновых комплексов элементов главных подгрупп в медицине, катализе и оптоэлектронике.
Литература
Lomova T.N., Tyulyaeva E.Y. New Trends in the Direct Synthesis of Phthalocyanine/Porphyrin Complexes. In: Direct Synthesis of Metal Complexes. (Kharisov B., Ed.) Amsterdam: Elsevier Science BV, 2018. p. 239-278.
https://doi.org/10.1016/B978-0-12-811061-4.00006-2
Sanders J.K.M., Bampos N., Clyde-Watson Z., Darling S.L., Hawley J.C., Kim H.-J., Mak C.C., Webb S.J. Axial Coordination Chemistry of Metalloporphyrins. In: The Porphyrin Handbook. Vol. 3 (Kadish K.M., Smith K.M., Guilard R., Eds.) Acad. Press, 2000. p. 1-48.
Lomova T.N., Berezin B.D. Koord. Khim. 1993, 19, 171-184.
Lomova T.N., Volkova N.I., Berezin B.D. Zh. Neorg. Khim. 1985, 30, 935-938.
Lomova T.N., Volkova N.I., Berezin B.D. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1988, 31, 75-81.
Ivanova S.S., Stuzhin P.A. J. Porphyrins Phthalocyanines 2011, 15, 1299-1309.
https://doi.org/10.1142/S108842461100421X
Lomova T. N., Klyueva M.E., Koifman O.I. Macroheterocycles 2015, 8, 32-46.
https://doi.org/10.6060/mhc140599l
Lomova T.N. Axially Coordinated Metal Porphyrins in Science and Practice. Moscow: KRASAND, 2018. 704 p.
Lomova T., Tsaplev Yu., Klyueva M., Ovchenkova E. J. Organomet. Chem. 2021, 945, 121880.
https://doi.org/10.1016/j.jorganchem.2021.121880
Subbotin N.B., Tomilova L.G., Kostromina N.A., Lukyanets E.A. Zh. Obshch. Khim. 1986, 56, 397-400.
Arnold J.J. Chem. Soc. Chem. Commun. 1990, 976-978.
https://doi.org/10.1039/c39900000976
Arnold J., Dawson D.Y., Hoffman C.G. J. Am. Chem. Soc. 1993, 115, 2707-2713.
https://doi.org/10.1021/ja00060a020
Arnold J. In: The Porphyrin Handbook, Vol. 3 (Kadish K.M., Smith K.M., Guilard R., Eds.) San Diego: Academic Press, 1999. p. 113-128.
Berezin B.D. Coordination Compounds of Porphyrins and Phthalocyanine. New-York, Toronto: Wiley, 1981. 280 p.
Molodkina O.V., Lomova T.N., Mozhzhukhina E.G. Russ. J. Gen. Chem. 2002, 72, 968-973.
https://doi.org/10.1023/A:1020407029048
Berezin B.D, Lomova T.N. Russ. J. Coord. Chem. 2001, 27, 85-104.
https://doi.org/10.1023/A:1009523115380
Brothers P.J. Adv. Organomet. Chem. 2001, 48, 289-432.
https://doi.org/10.1016/S0065-3055(01)48003-8
Lomova T.N., Zaitseva S.V., Molodkina O.V., Ageeva T.A. Russ. J. Coord. Chem. 1999, 25, 397-401.
Lomova T.N., Molodkina O.V., Pilipets O.V. Molecules 2000, 5, 1500-1501
https://doi.org/10.3390/51201461
Marrese C.A., Carrano C. J. Inorg. Chem. 1983, 22, 1858-1862.
https://doi.org/10.1021/ic00155a007
Stuzhin P.A., Goryachev M.Yu., Ivanova S.S., Nazarova A., Pimkov I., Koifman O.I. J. Porphyrins Phthalocyanines 2013, 17, 905-912.
https://doi.org/10.1142/S1088424613500892
Munro O.Q., Coutsolelos A.G., Chengc B., Scheidt W.R. J. Porphyrins Phthalocyanines 2019, 23, 969-989.
https://doi.org/10.1142/S1088424619500834
Eisner U., Harding M.J.C. J. Chem. Soc. 1964, 4089-4101.
https://doi.org/10.1039/jr9640004089
Fuhrhop J.-H., Lumbantobing T. Tetrahedron Lett. 1970, 2815.
https://doi.org/10.1016/S0040-4039(01)98348-0
Buchler J.W., Puppe L., Schneehage H.H. Liebigs Ann. Chem. 1971, 749, 134-145.
https://doi.org/10.1002/jlac.19717490115
Abdo S., Cruz M.I., Fripiat J.J. Clay Clay Miner. 1980, 28, 125-129.
https://doi.org/10.1346/CCMN.1980.0280208
Arnold D., Blok J. Coord. Chem. Rev. 2004, 248, 299-319.
https://doi.org/10.1016/j.ccr.2004.01.004
Belcher W.J., Hodgson M.C., Sumida K., Torvisco A., Ruhlandt-Senge K., Ware D.C., Boyd P.D.W., Brothers P.J. Dalton Trans. 2008, 1602-1614.
https://doi.org/10.1039/b716189a
Novikova N., Brothers P.J., Simpson M.C. Int. J. Nanotech. 2014, 11, 713-723.
https://doi.org/10.1504/IJNT.2014.060594
Novikova N.I., Lo A.S.V., Gordon K.C., Brothers P.J., Simpson M.C. J. Phys. Chem. A 2018, 122, 5121-5131.
https://doi.org/10.1021/acs.jpca.8b01925
Stuzhin P.A., Skvortsov I.A., Zhabanov Yu.A., Somov N.V., Razgonyaev O.V., Nikitin I.A., Koifman O.I. Dyes Pigm. 2019, 162, 888-897.
https://doi.org/10.1016/j.dyepig.2018.11.006
Ivanova S.S., Lebedeva I.A., Somov N.V., Marova A.A., Popov A., Stuzhin P.A. Macroheterocycles 2019, 12, 276-281.
https://doi.org/10.6060/mhc190126s
Lomova T.N., Klyueva M.E., Tyulyaeva E.Yu., Mozhzhukhina E.G., Molodkina О.V. J. Phys. Org. Chem. 1997, 10, 144.
Molodkina О.V., Lomova T.N., Mozhzhukhina E.G. Russ. Chem. Bull. 1998, 47, 1996-1999.
https://doi.org/10.1007/BF02494515
Boitrel B., Breede M., Brothers P.J., Hodgson M., Michaudet L., Rickard C.E.F., Salim N. L. Dalton Trans. 2003, 1803-1807.
https://doi.org/10.1039/b210318d
Lemon C.M., Brothers P.J., Boitrel B. Dalton Trans. 2011, 40, 6591-6609.
https://doi.org/10.1039/c0dt01711f
Girichev G.V., Giricheva N.I., Koifman O.I., Minenkov Yu.V., Pogonin A.E., Semeikin A.S., Shlykov S.A. Dalton Trans. 2012, 41, 7550-7558.
https://doi.org/10.1039/c2dt12499h
Grinberg A.A. Introduction to the Сhemistry of Сomplex Сompounds. 4th ed. Leningrad: Khimiya, 1971. 632 p.
Cotton F.A., Wilkinson G., Gaus P.L. Basic Inorganic Chemistry, 3rd Edition. John Wiley & Sons, 1995. 856 p.
Batsanov S.S. Structural Chemistry: Facts and Dependencies. Moscow: Dialog-MGU, 2000. 292 p.
Sayer P., Gouterman M., Connel C.R. J. Am. Chem. Soc. 1977, 99, 1082-1087.
https://doi.org/10.1021/ja00446a018
Carrano C.J., Tsutsui M. J. Coord. Chem. 1977, 7, 79-83.
https://doi.org/10.1080/00958977708073043
Yamamoto Y., Nadano R., Itagaki M., Akiba, K.-Y. J. Am. Chem. Soc. 1995, 117, 8287-8288.
https://doi.org/10.1021/ja00136a034
Yamamoto Y., Akiba K.-Y. J. Organomet. Chem. 2000, 611, 200-209.
https://doi.org/10.1016/S0022-328X(00)00447-2
Yamamoto A., Satoh W., Yamamoto Y., Akiba K.-Y. Chem. Commun. 1999, 147-148.
https://doi.org/10.1039/a809601e
Grubisha D.S., Guzei I.A., Al-Salim N., Boyd P.D.W., Brothers P.J., Woo L.K. Angewandte Chemie Int. Ed. 2001, 40, 4743-4745.
https://doi.org/10.1002/1521-3773(20011217)40:24<4743::AID-ANIE4743>3.0.CO;2-H
Davydov D.R., Ponomarev G.V., Bobrovnikova-Marjon E., Haines D.C., Peterson J.A. Biotechnol. Appl. Biochem. 2013, 60, 41-51.
https://doi.org/10.1002/bab.1085
Brothers P.J. J. Porphyrins Phthalocyanines 2002, 6, 259-267.
https://doi.org/10.1142/S1088424602000294
Meerovich G., Zherdeva V.V., Lukyanets E.A., Derkacheva V.M., Vorozhtsov G.N., Meerovich G.A., Kogan E.A., Savitsky A.P. Clinical Lasers and Diagnostics 2001, 4156, 96-102.
Pankratov A.A, Andreeva T.N., Yakubovskaya R.I., Kogan B. Ya., Butenin A.V., Feizulova R K.-G., PuchnovaV.A., Novoseletsky N.V., KhromovA.V., Lukyanets E.A., Vorozhtsov G.N. Bull. Exp. Biol. Med. 2014, 157, 798-803.
https://doi.org/10.1007/s10517-014-2670-2
Makarova E.A., Dudkin S.V., Lukyanets E.A. J. Porphyrins Phthalocyanines 2013, 17, 785-790.
https://doi.org/10.1142/S1088424613500338
Meerovich I.G., Jerdeva V.V., Derkacheva V.M., Meerovich G.A. Lukyanets E.A., Kogan E.A., Savitsky A.P. J. Photochem. Photobiol. B 2005, 80, 57-64.
https://doi.org/10.1016/j.jphotobiol.2004.12.008
Meerovich I.G., Jerdeva V.V., Derkacheva V.M. Laser Applications in Medicine, Biology, and Environmental Science 2003, 5149, 128-134.
Ríos M.-C., Bravo N.-F., Sánchez C.-C., Portilla J. RSC Adv. 2021, 11, 34206-34234.
https://doi.org/10.1039/D1RA06567J
Safonova E.A., Kolomeuchuk F.M., Meshkov I.N., Gorbunova Yu.G., Tsivadze A.Yu. 11th International Conference on Porphyrins and Phthalocyanines (ICPP-11). Buffalo, New York, USA. 2020. Book of Abstracts. 299.
Ahmetali E., Atmaca G.Y., Karaoğlu H.P., Erdoğmuş A., Koçak M.B. J. Porphyrins Phthalocyanines 2019, 23, 960-968.
https://doi.org/10.1142/S108842461950055X
Cooper Sh.A.L., Graepel K.W., Steffens R.S., Dennis D.G., Cambroneo G.A., Wiggins R.Q., Ruppel J.V., Snyder N.L. J. Porphyrins Phthalocyanines 2019, 23, 850-855.
https://doi.org/10.1142/S1088424619500597
D'Andrea A., Pomarico G., Nardis S., Paolesse R., Natale C. D., Lvova L. J. Porphyrins Phthalocyanines 2019, 23, 117-124
https://doi.org/10.1142/S1088424619500159
Soy R.C., Babu B., Oluwole D.O., Nwaji N., Oyim J., Amuhay E, Prinsloo E., Mack J., Nyokong T. J. Porphyrins Phthalocyanines 2019, 23, 34-45.
https://doi.org/10.1142/S1088424618501146
Hamdoush M., Somov N.V., Ivanova S.S., Stuzhin P.A. Macroheterocycles 2020, 13, 19-22.
https://doi.org/10.6060/mhc190970s
Hojniak-Thyssen S., Szczepaniak M., Latos-Graz˙yn'ski L., Pacholska-Dudziak E. J. Porphyrins Phthalocyanines 2019, 23, 1470-1477.
https://doi.org/10.1142/S1088424619501621
Molupe N., Babu B., Prinsloo E., Kaassis A.Y.A., Edkins K., Mack J., Nyokong T. J. Porphyrins Phthalocyanines 2019, 23, 1486-1494.
https://doi.org/10.1142/S1088424619501633
Atmaca G.Y., Erdoğmuş A. J. Porphyrins Phthalocyanines 2019, 23, 1398-1405.
https://doi.org/10.1142/S1088424619501487
Zarrabi N., Holzer N., Bayard B.J., Seetharaman S., Boe B.G., D'Souza F., Poddutoori P.K. J. Porphyrins Phthalocyanines 2021, 25, 456-468.
https://doi.org/10.1142/S1088424621500267
Izawa M., Nakai A., Suito T., Tanaka T., Osuka A. J. Porphyrins Phthalocyanines 2020, 25, 400-406.
https://doi.org/10.1142/S1088424621500103
Brothers P. Organoelement Chemistry of Main-Group Porphyrin Complexes. In: Advances in Organometallic Chemistry, V. 48 Academic Press, 2001. p. 289-342.
https://doi.org/10.1016/S0065-3055(01)48003-8
Novakova V., Donzello M.P., Ercolani C., Zimcik P., Stuzhin P.A. Coord. Chem. Rev. 2018, 361, 1-73.
https://doi.org/10.1016/j.ccr.2018.01.015
Guilard R., Pichon-Pesme V., Lachekar H., Lecomte C., Aukauloo A.M., Boulas E.L., Kadish K.M. J. Porphyrins Phthalocyanines 1997, 1, 109-119.
https://doi.org/10.1002/(SICI)1099-1409(199704)1:2<109::AID-JPP13>3.3.CO;2-W
Guilard R., Zrineh A., Tabard A., Endo A., Han B.C., Lecomte C., Souhassou M., Habbou A., Ferhat M., Kadish K.M. Inorg. Chem. 1990, 29, 4476-4482.
https://doi.org/10.1021/ic00347a029
Kadish K.M., Dubois D., Koeller S., Barbe J.M., Guilard R. Inorg. Chem. 1992, 31, 3292-3294.
https://doi.org/10.1021/ic00041a024
Flitsch W. Adv. Heterocycl. Chem. 1988, 43, 73-126.
https://doi.org/10.1016/S0065-2725(08)60253-6
Hopf F., Whitten D.G. Chemical Transformations Involving Photoexcited Porphyrins and Metalloporphyrins. In: The Porphyrins, Vol. 2 (Dolphin D., Ed) New York: Academic Press., 1978. p. 161-195.
https://doi.org/10.1016/B978-0-12-220102-8.50013-0
Lurie Yu.Yu. Analytical Chemistry Handbook. Moscow: Chemistry, 1967. 390 p.
The Porphyrins, Vol. 5 (Dolphin D., Ed) New York: Academic Press, 1978. p. 53 .
Peychal-Heiling G., Wilson G. Anal. Chem. 1971, 43. 550-556.
https://doi.org/10.1021/ac60299a002
Ferguson J.A., Meyer T.J., Whitten D.G. Inorg. Сhem. 1972, 11, 2767.
https://doi.org/10.1021/ic50117a038
Blinova I.A., Vasiliev V.V. In: I Int. Conf. on Biocoord. Chemistry. Ivanovo. 1994. Book of Abstracts. p. 111.
Kadish K.M., Ou Z., Adamian V.A., Guilard R., Gros C.P., Erben C., Will S., Vogel E. Inorg. Chem. 2000, 39, 5675-5682.
https://doi.org/10.1021/ic0010196
Boucher L.J. Coord. Chem. Rev. 1972. 7, 289-329.
https://doi.org/10.1016/S0010-8545(00)80024-7
Lomova T.N., Berezin B.D. Russ. J. Coord. Chem. 2001, 27, 85-104.
https://doi.org/10.1023/A:1009523115380
Kuz'mitskii V.A., Solov'ev K.N., Tsvirko M.P. Porphyrins: Spectroscopy, Electrochemistry, Application (Enikolopyan N.S., Ed.) Moscow: Nauka, 1987. 384 p.
Barbe J.M., Ratti C., Richard P., Lecomte C., Gerardin R., Guilard R. Inorg. Chem. 1990, 29, 4126-4130.
https://doi.org/10.1021/ic00345a043
Kadish K.M., Dubois D., Barbe J. M., Guilard, R. Inorg. Chem. 1991, 30, 4498-4501.
https://doi.org/10.1021/ic00024a007
Schaffer A.M., Gouterman M. Theor. Chim. Acta 1970, 18, 1-13.
https://doi.org/10.1007/BF00533692
Balch A.L., Latos-Grazynski L., Noll, B.C., Phillips S.L. Inorg. Chem. 1993, 32, 1124-1129.
https://doi.org/10.1021/ic00059a017
Yamamoto Y., Nadano R., Itagaki M., Akiba K.-Y. J. Am. Chem. Soc. 1995, 117, 8287-8288.
https://doi.org/10.1021/ja00136a034
Satoh W., Nadano R. Yamamoto G., Yamamoto Y., Akiba K.-Y. Organometallics 1997, 16, 3664-3671.
https://doi.org/10.1021/om970231n
Lomova T.N., Mozhzhukhina E.G., Shormanova L.P., Berezin B.D. J. Gen. Chem. USSR (Engl. Transl.) 1989, 59, 2077-2086
Lomova T.N., Zaitseva S.V., Zdanovich S.A. XIII Symposium on Intermolecular Interactions and Conformations of Molecules. St. Petersburg 2006. 162.
Lomova T.N., Klyueva M.E., Mozhzhukhina E.G., Tyulyaeva E.Yu., Bichan N.G., Zaitseva S.V., Zdanovich S.A. Russ. J. Struct. Chem. 2014, 55, 180-190.
https://doi.org/10.1134/S0022476614010314
Mack J., Stillman M.J. J. Porphyrins Phthalocyanines 2001, 5, 67-76.
https://doi.org/10.1002/1099-1409(200101)5:1<67::AID-JPP300>3.0.CO;2-3
Lomova T.N. Reactivity of metal porphyrins during dissociation in solutions. In: The solution chemistry and the technology of liquid phase materials. Achievements and prospects. (Zakharov A.G., Ed.) Ivanovo: Institute of solution chemistry RAS, 2006. p. 206-226.
Bhat I.A., Soman S., Chandra B., Sahoo S., Thaltiri V., Panda P.K. J. Porphyrins Phthalocyanines 2021, 25, 1015-1021.
https://doi.org/10.1142/S1088424621501005
Cheng M.H.Y., Cevallos A., Rajora M.A., Zheng G. J. Porphyrins Phthalocyanines 2021, 25, 703-713.
https://doi.org/10.1142/S1088424621500656
Al-Khaza'leh K.A., Omar K., Jaafar M.S. African Journal of Biotechnology 2011, 10, 9137-9147.
Ravikumar M., Kathiravan A., Neels A., Mothi E.M. Eur. J. Inorg. Chem. 2018, 2018, 3868-3877.
https://doi.org/10.1002/ejic.201800645
Kadish K.M., Tabard A.,Van Caemelbecke E., Aukauloo A.M., Richard P,. Guilard R. Inorg. Chem. 1998, 37, 6168-6175.
https://doi.org/10.1021/ic971534c
Ravikumar M., Raghav D., Rathinasamy K., Kathiravan A., Mothi E.M. ACS Appl. Bio Mater. 2018, 1, 1705−1716.
https://doi.org/10.1021/acsabm.8b00507
Khisaa J., Derese S., Mack J., Amuhaya E., Nyokong T. J. Porphyrins Phthalocyanines 2021, 25, 794-799.
https://doi.org/10.1142/S1088424621500462
Igarashi T., Konishi K., Aida T. Chem. Lett. 1998, 1039-1040.
https://doi.org/10.1246/cl.1998.1039
Shiragami T., Kubomura K., Ishibashi D., Inoue H. J. Am. Chem. Soc. 1996. 118, 6311-6312.
https://doi.org/10.1021/ja960020u
Handman J., Harriman A., Porter G. Nature 1984, 307, 534-535.
https://doi.org/10.1038/307534a0
Szulbinski W., Strojek J.W. Inorg. Chim. Acta 1986, 118, 91-97.
https://doi.org/10.1016/S0020-1693(00)81367-5
Duan M.-Y., Li J., Mele G., Wang C., Lu X.-F., Vasapollo G., Zhang F.-X. J. Phys. Chem. C 2010, 114, 7857-7862.
https://doi.org/10.1021/jp911744a
Song Y., Yang Y., Medforth C.J., Pereira E., Singh A.K., Xu H., Jiang Y., Brinker J., Van Swol F., Shelnutt JA. J. Am. Chem. Soc. 2004, 126, 635-645.
https://doi.org/10.1021/ja037474t
Wang Z.C., Medforth C.J., Shelnutt J.A. J. Am. Chem. Soc. 2004, 126: 16720-16721.
https://doi.org/10.1021/ja044148k
Olijvea L.L.C., How E.N.W., Bhadbhade M., Prasad S., Colbran S.B., Zhao C., Thordarson P. J. Porphyrins Phthalocyanines 2011, 15, 1345-1353
https://doi.org/10.1142/S1088424611004312
Miao Q., Liu Q., Sun E., Ren T., J. Photochem. Photobiol. A Chem. 2016, 316, 19-23.
https://doi.org/10.1016/j.jphotochem.2015.10.006
Dubinina T.V., Osipova M.M., Zasedatelev A.V., Krasovskii V.I. , Borisova N.E., Trashin S.A., Tomilova L.G., Zefirov N.S. Dyes Pigm. 2016, 128, 141-148.
https://doi.org/10.1016/j.dyepig.2016.01.023
McEwan K., Lewis K., Yang Y.-V., Chng L.-L., Lee Y.-W., Lau W.-P., Lai K.-S. Advanced Functional Materials 2003, 13, 863-867.
https://doi.org/10.1002/adfm.200304288
Senge M.O., Fazekas M., Notaras E.G.A., Blau V.J., Zawadzka M., Locos O.B., Ni Mhuircheartaigh E.M. Advanced Materials 2007, 19, 2737-2774.
https://doi.org/10.1002/adma.200601850
Borges-Martínez M., Montenegro-Pohlhammer N., Zhang X., Galvez-Aranda D.E., Ponce V., Seminario J.M., Cárdenas-Jirón G. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2022, 269, 120740.
https://doi.org/10.1016/j.saa.2021.120740
Hamdoush M., Ivanova S.S., Pakhomov G.L., Stuzhin P.A. Macroheterocycles 2016, 9, 230-233.
https://doi.org/10.6060/mhc160424s
Hamdoush M., Skvortsov I.A., Mikhailov M.S., Pakhomov G.L., Stuzhin P.A. J. Fluorine Chem. 2017, 204, 31-36.
https://doi.org/10.1016/j.jfluchem.2017.10.007
Pakhomov G.L., Travkin V.V., Hamdoush M., Zhabanov Yu.A., Stuzhin P.A. Macroheterocycles 2017, 10, 548-551.
https://doi.org/10.6060/mhc171038s
Lomova T.N., Malov M.E., Klyuev M.V., Troshin P.A. Macroheterocycles 2009, 2, 57-59.
https://doi.org/10.6060/mhc2009.2.164
Ovchenkova E.N., Bichan N.G., Lomova T.N. Russ. J. Inorg. Chem. 2018, 63, 391-399.
https://doi.org/10.1134/S0036023618030178
Lomova T.N., Malov M.E., Klyuev M.V., Troshin P.A. Advances in Materials Science Research. V. 2, (Wythers M.C.N.Y.) New York: Nova Science Publ., 2016. pp. 143-154.
Lomova T.N., Motorina E.V., Klyuev M.V. Macroheterocycles 2013, 6, 327-333.
https://doi.org/10.6060/mhc130644l
Motorina E.V., Lomova T.N., Troshin P.A., Klyuev M.V. Russ. J. Gen. Chem. 2014, 84, 946-952.
https://doi.org/10.1134/s1070363214050272
Lapshin A.N. Dis. cand. chem. Scie., Chernogolovka: IPCP RAS. 2006. 120 p.
Koeppe R., Troshin P., Luybovskaya R., Sariciftci N. Appl. Phys. Lett. 2005, 87, 244102.
https://doi.org/10.1063/1.2146070
Koeppe R., Troshin P., Fuchsbauer A., Luybovskaya R., Sariciftci N. Fuller. Nanotub. Carb. Nanosruct. 2006, 14, 441-446.
https://doi.org/10.1080/15363830600666118
Lomova T. Appl. Organomet. Chem. 2021, 35(8), e6254
https://doi.org/10.1002/aoc.6254
Shorin V.A., Maslennikov S., Fedorov M.I., Lomova T.N., Molodkina O.V. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1999, 42, 89-93.
Troshin P.A., Troyanov S.I., Boiko G.N., Lyubovskaya R.N., Lapshin A.N., Goldshleger N.F. Full. Nanotub. Carb. Nanostr. 2004, 12, 413-419.