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Boron Dipirrins: Mechanism of Formation, Spectral and Photophysical Properties, and Directions of Functionalization

  • Selected articles originally published in Russian in Rossiiskii Khimicheskii Zhurnal (Russian Chemistry Journal)
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Abstract

Boron dipyrrins (Bodipy) are unique complexes occupying an intermediate position between classical coordination and organometallic compounds. The enormous interest of researchers from all over the world to the compounds of this class has by now provided an endless stream of publications that requires generalization. Existing reviews and original publications do not fully cover the structural diversity of Bodipy and their possible applications in engineering, medicine, analytical chemistry, optics, photonics, etc. In this paper, w e present the results, mainly of our own research, which for the first time allowed us to establish the physicochemical principles of the formation of Bodipy (the reasons for the low rates of complexation of ligands with boron trifluoride), changes in the spectral and photophysical properties of alkylated Bodipy complexes with the separation of contributions from universal and specific solvation, and examples of functionalization of inorganic and organic polymer materials based on Bodipy of different structures. Examples of the current team’s Bodipy research in different practical areas are presented.

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References

  1. Akchurin, I.O., Bochkov, A.Yu., and Traven’, V.F., Usp. Khim. Khim. Tekhnol., 2011, vol. 25, no.11, issue 127, pp. 36–40.

    Google Scholar 

  2. Efimov, V.A., Fedyunin, S.V., and Chakhmakhcheva, O.G., Bioorg. Khim., 2011, vol. 37, no. 2, pp. 278–283.

    CAS  PubMed  Google Scholar 

  3. Pakhomov, A.A., Martynov, V.I., Kononevich, Y.N., Korlyukov, A.A., and Muzafarov, A.M., Mendeleev Commun., 2016, vol. 26, no. 3, pp. 196–198.

    CAS  Google Scholar 

  4. Jiang, X.-D., Li, S., Guan, J., Fang, T., Liu, X., and Xiao, L.-J., Curr. Org. Chem., 2016, vol. 20, no. 16, pp. 1736–1744.

    CAS  Google Scholar 

  5. Boens, N., Verbelen, B., and Dehaen, W., Eur. J. Org. Chem., 2015, vol. 2015, no. 30, pp. 6577–6595.

    CAS  Google Scholar 

  6. Schmitt, A., Hinkeldey, B., Wild, M., and Jung, G., J. Fluoresc., 2009, vol. 19, no. 4, pp. 755–759.

    CAS  PubMed  Google Scholar 

  7. Tram, K., Yan, H., Jenkins, H.A., Vassiliev, S., and Bruce, D., Dyes Pigments, 2009, vol. 82, no. 3, pp. 392–395.

    CAS  Google Scholar 

  8. Descalzo, A.B., Xu, H.-J., Xue, Z.-L., Hoffmann, K., Shen, Z., et al., Org. Lett., 2008, vol. 10, pp. 1581–1584.

    CAS  PubMed  Google Scholar 

  9. Haugland, R.P., Handbook of Fluorescent Probes and Research Chemicals, 6th ed, Molecular Probes: Eugene. OR. 1996.

    Google Scholar 

  10. Awuah, S.G., Polreis, J., and Biradar, V., J. Org. Lett., 2011, vol. 13, pp. 3884–3887.

    CAS  Google Scholar 

  11. Boyer, J.H., Haag, A.M., Sathyamoorthi, G., Soong, M.L., Thangaraj, K., and Pavlopouloset, T.G., Heteroat. Chem., 1993, vol. 4, pp. 39–49.

    CAS  Google Scholar 

  12. Yogo, T., Urano, Y., Mizushima, A., Sunahara, H., Inoue, T., Hirose, K., Iino, M., Kikuchi, K., and Nagano, T., PNAS, 2008, vol. 105, no. 1, pp. 28–32.

    CAS  PubMed  Google Scholar 

  13. Pang, W., Zhang, X.-F., Zhou, J., Yu, C., Hao, E., and Jiao, L., Chem. Commun., 2012, vol. 48, pp. 5437–5439.

    CAS  Google Scholar 

  14. Ran, S., Xu, X., Scott, B.R., Ferrara, B.J., Neal, K., Bacskai, B.J., Medarova, Z., and Moore, A., J. Am. Chem. Soc., 2009, vol. 131, pp. 15257–15261.

    CAS  PubMed  PubMed Central  Google Scholar 

  15. Yutanova, S.L., Kuznetsova, R.T., Aksenova, Yu.V., Tel’-minov, Ye.N., and Berezin, M.B., Izv. Vyssh. Uchebn. Zaved. Fiz., 2013, vol. 56, no. 3, pp. 23–27.

    Google Scholar 

  16. Driessen, O. and Lugtenberg, J., J. High Resolution Chromatogr. Chromatogr. Commun., 1980, vol. 3, pp. 405.

    CAS  Google Scholar 

  17. Goze, C., Ulrich, G., Charbonniere, L., Cesario, M., and Prange, T., Chem. Eur. J., 2003, vol. 9, pp. 3748–3752.

    CAS  PubMed  Google Scholar 

  18. Coskun, A., Baytekin, B.T., and Akkaya, E.U., Tetrahedron Lett., 2003, vol. 44, pp. 5649–5653.

    CAS  Google Scholar 

  19. Cha, N.R., Moon, S.Y., and Chang, S.-K., Tetrahedron Lett., 2003, vol. 44, pp. 8265–8270.

    CAS  Google Scholar 

  20. Kollmannsberger, M., Rurack, K., Resch-Genger, U., Rettig, W., and Daub, J., Chem. Phys. Lett., 2000, vol. 329, pp. 363–367.

    CAS  Google Scholar 

  21. Rurack, K., Sczepan, M., Spieles, M., Resch-Genger, U., and Rettig, W., Chem. Phys. Lett., 2000, vol. 320, pp. 87–95.

    CAS  Google Scholar 

  22. Gabe, Y., Urano, Y., Kikuchi, K., Kojima, H., and Nagano, T., J. Am. Chem. Soc., 2004, vol. 126, pp. 3357–3363.

    CAS  PubMed  Google Scholar 

  23. Rurack, K., Kollmannsberger, M., and Daub, J., New J. Chem., 2001, vol. 25, pp. 289–295.

    CAS  Google Scholar 

  24. Gareis, T., Huber, C., and Wolfbeis, O.S., J. Chem. Commun., 1997, pp. 1717–1719.

    Google Scholar 

  25. Baki, C.N. and Akkaya, E.U., J. Org. Chem., 2001, vol. 66, pp. 1512–1513.

    CAS  PubMed  Google Scholar 

  26. Soper, S.A., Owens, C., Lassiter, S., Xu, Y., and Waddell, E., Topics in Fluorescence Spectroscopy, Lakowicz, J.R., Ed., New York: Kluwer, 2003, vol. 7, pp. 1–68.

    CAS  Google Scholar 

  27. Ulrich, G., Goze, C., Guardigli, M., Roda, A., and Ziessel, R., Ang. Chem. Int. Ed., 2005, vol. 44, pp. 3694–3698.

    CAS  Google Scholar 

  28. Levitt, J.A., Kuimova, M.K., Yahioglu, G., Chung, P., and Suhling, K., J. Phys. Chem. C., 2009, vol. 113, pp. 11634–11642.

    CAS  Google Scholar 

  29. Erten-Ela, S., Yilmaz, M.D., Icli, B., Dede, Y., Icli, S., and Akkaya, E.U., Org. Lett., 2008, vol. 10, pp. 3299–3302.

    CAS  PubMed  Google Scholar 

  30. Sabatini R.P., McCormick T., Lazarides T., Wilson K.C., Eisenberg, R., and McCamant, D. W., J. Phys. Chem. Lett., 2011, no. 3, pp. 223–227. doi: 10.1021/jz101697y

    Google Scholar 

  31. Sazanovich, I.V., Kirmaier, Ch., Hindin, E., Yu, L., Bocian, D.F., Lindsey, J.S., and Holten, D., J. Am. Chem. Soc., 2004, vol. 126, pp. 2664.

    CAS  PubMed  Google Scholar 

  32. Surya, P. and Gayathri, T., EurJOC, 2014, vol. 2014, no. 22, pp. 4689–4707.

    Google Scholar 

  33. Yang, L., Liu, J.H., Liang, H., and Jianrong, G., J. Photo-chem. Photobiol. A: Chem., 2017, vol. 332, pp. 283.

    CAS  Google Scholar 

  34. Yamazawa, S., Nakashima, M., Suda, Y., Nishiiabu, R., and Kubo, Y., J. Org. Chem., 2016, vol. 81, no. 3, pp. 1310–1315.

    CAS  PubMed  Google Scholar 

  35. Yakubovskyi, V., Didukh, N., Zatsikha, Yu., and Kovtun, Yu., Chem. Select, 2016, vol. 1, no. 7, p. 1462

    CAS  Google Scholar 

  36. Pang, W., Zhang, X.-F., Zhou, J., Yu, C., and Hao, E., Chemical communications (Cambridge, England). 2012, vol. 48, pp. 5437–5439.

    CAS  Google Scholar 

  37. Rumyantsev, E.V., Aleshin, S.N., Desoki, A., Marfin, Yu.S., and Antina, E.V., Russ. J. InOrg. Chem., 2013, vol. 58, no. 5, p. 506. 10.1134/S0036023613050197

    Google Scholar 

  38. Rumyantsev, E.V., Desoki, A., Marfin, Yu.S., and Antina, E.V., Russ. J. Gen. Chem., 2010, vol. 80, no. 9, p. 1871. https://doi.org/10.1134/S1070363210090264

    CAS  Google Scholar 

  39. Rumyantsev, E.V., Marfin, Yu.S., and Antina E.V., Izv. Akad. Nauk, Ser. Khim., 2010, no. 10, pp. 1840–1845.

    Google Scholar 

  40. Gonzalez-Valls, Mirloup, A., Bahers, T.Le, Keller, N., Cottineau, T., Sautet, P., and Keller, V., RSC Adv., 2016, vol. 6, no. 94, pp. 91529–91540.

    CAS  Google Scholar 

  41. Bol’shakov, G.F., Infrakrasnye spektry i rentgeno-grammy geteroorganicheskikh soedinenii (Infrared Spactra and X-Day Patterns of Hetero-Organic Compounds), Leningrad: Khimiia, 1967.

    Google Scholar 

  42. Goze, C., Ulrich, G., and Ziessel, R., Org. Lett., 2006, vol. 8, no. 20, pp. 4445–4448.

    CAS  PubMed  Google Scholar 

  43. Gur’yanova, E.N., Donorno-aktseptornaya svyaz’ (Donor-Acceptor Bond), Moscow: Khimiia, 1973.

    Google Scholar 

  44. Andrews, L.J. and Keefer, R.M., Molecular Complexes in Organic Chemistry, San Francisco: Holden-Day, 1964.

    Google Scholar 

  45. Graham, W.A.G. and Stone, F.G.A., J. Inorg. Nucl. Chem., 1956, vol. 3, pp. 165–177.

    Google Scholar 

  46. Volkov, A.F., Romm, I.P., Gur’yanova, Ye.N., and Kocheshkov, K.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1976, no. 6, pp. 1365–1367.

    Google Scholar 

  47. Grabowski, S., Hydrogen Bonding - New Insights, Dordrecht: Springer, 2006. 519 p.

    Google Scholar 

  48. Shmidt, F.K., Koordinatsionno-khimicheskie osnovy metal-lokompleksnogo kataliza (Coordination Chemical Principles of Metallocomplex Catalysis), Irkutsk: Irkutsk. Gos, Univ., 1981.

    Google Scholar 

  49. Marfin, Yu.S., Rumyantsev, E.V., Fadeev, Ya.S., and Antina, E.V., Russ J. Phys. Chem. A, 2012, vol. 86, no. 7, p. 1068. https://doi.org/10.1134/S0036024412070163

    CAS  Google Scholar 

  50. Aleksakhina, E.L., Marfin, Yu.S., Merkushev, D.A., Tomilova, I.K., and Rumyantsev, E.V., Kazan. Med. Zh., 2015, vol. 96, no. 5, pp. 792–798.

    Google Scholar 

  51. Marfin, Yu.S., Merkushev, D.A., Rumyantsev, E.V., Aleksakhina, E.L., and Tomilova, I.K., J. Fluoresc., 2016, vol. 26, no. 1, pp. 255–261.

    CAS  PubMed  Google Scholar 

  52. Marfin, Yu.S., Shipalova, M.V., Kurzin, V.O., Ksenofon-tova, K.V., Solomonov, A.V., and Rumyantsev, E.V., J. Fluoresc., 2016, vol. 26, no. 6, pp. 2105–2112.

    CAS  PubMed  Google Scholar 

  53. Marfin, Yu.S., Vodyanova, O.S., Merkushev, D.A., Usoltsev, S.D., Kurzin, V.O., and Rumyantsev, E.V., J. Fluoresc., 2016, vol. 26, no. 6, pp. 1975–1985.

    CAS  PubMed  Google Scholar 

  54. Bobrov, A.V., Marfin, Yu.S., Kuznetsov, V.V., and Rumyantsev, E.V., Mater. Technol., 2016, pp. 1–8. https://doi.org/10.1080/10667857.2016.1154261.

    Google Scholar 

  55. Duman, S., Cakmak, Y., Kolemen, S., Akkaya, E., and Dede, Y., Org. Chem., 2012, vol. 77, pp. 4516–4527

    CAS  Google Scholar 

  56. Buyuktemiz, M., Duman, S., and Dede, Y., J. Phys. Chem. A, 2013, vol. 117, pp. 1665–1669.

    CAS  PubMed  Google Scholar 

  57. Antina, E.V., Khimiya bilirubina i еgo analogov (Chemistry of Bilirubin and Its Analogs), Moscow: KRASAND, 2009.

    Google Scholar 

  58. Pardoen, J.A., Lugtenburg, J., and Canters, G.W., J. Phys. Chem., 1985, vol. 89, pp. 4272–4277.

    CAS  Google Scholar 

  59. Lee, J-S., Kim, H.K., Feng, S., Vendrell, M., and Chang, Y.-T., Chem. Commun., 2011, vol. 47, pp. 2339–2341.

    CAS  Google Scholar 

  60. López Arbeloa, F., Bañuelos, J., Martínez, V., Arbeloa, T., and López Arbeloa, I., Int. Rev. Phys. Chem., 2005, vol. 24, pp. 339–374.

    Google Scholar 

  61. Werner, T., Huber, C., Heinl, S., Kollmannsberger, M., Daub, J., and Wolfbeis, O.S., Fresenius J. Anal. Chem., 1997, vol. 359, pp. 150–154.

    CAS  Google Scholar 

  62. Thoresen, L.H., Kim, H., Welch, M.B., Burghart, A., and Burgess, K., ChemInfo, 1998, vol. 30, pp. 1276–1281.

    Google Scholar 

  63. Burghart, A., Kim, H., Welch, M.B., Thoresen, L.H., Reibenspies, J., Burgess, K., Bergström, F., and Johansson, L.B.-A., J. Org. Chem., 1999, vol. 64, pp. 7813–7819.

    CAS  Google Scholar 

  64. Rurack, K. and Kollmannsberger, M., New J. Chem., 2001, vol. 25, pp. 289–292.

    CAS  Google Scholar 

  65. Coskun, A. and Akkaya, E.U., Tetrahedron Lett., 2004, vol. 45, pp. 4947–4949.

    CAS  Google Scholar 

  66. Kang, H.C. and Haugland, R.P., US Patent 5. 433. 896, 1995.

    Google Scholar 

  67. Qin, W., Rohand, T., Baruah, M., and Stefan, A., Chem. Phys. Lett., 2006, vol. 420, pp. 562–568.

    CAS  Google Scholar 

  68. Rumyantsev, E.V., Marfin, Yu.S., Solomonov, A.V., and Timin, A.S., XX Mendeleevskii s”yezd po obshchei i prikladnoi khimii (XX Mendeleev Congress on General and Applied Chemistry), Yekaterinburg, 2016, vol. 1, p. 96.

    Google Scholar 

  69. Menges, N., Comput. Theor. Chem., 2015, vol. 1068, pp. 117–122.

    CAS  Google Scholar 

  70. Uzhinov, B.M., Ivanov, V.L., and Mel’nikov, M.Ya., Usp. Khim., 2011, vol. 80, no. 12, pp. 1231–1242.

    Google Scholar 

  71. Hattori, S., Ohkubo, K., Urano, Y., Sunahara, H., Nagano, T., Wada, Yu., Tkachenko, N.V., Lemmetyinen, H., and Fukuzumi, S., J. Phys. Chem. B, 2005, vol. 2005, no. 109, pp. 32–15368.

    Google Scholar 

  72. Hu, R., Lager, E., Aguilar-Aguilar, A., Liu, J., Lam, J.W.Y., Sung, H.H.Y., Williams, I.D., Zhong, Y., Wong, K.S., Peña-Cabrera, E., and Tang, B.Z., J. Phys. Chem. C, 2009, vol. 113, no. 36, pp. 15845–15853.

    CAS  Google Scholar 

  73. Scalise, R.E., Caradonna, P.A., Tracy, H.J., Mullin, J.L., and Keirstead, A.E., J. Inorg. Organomet. Polym. Mater., 2014, vol. 24, no. 2, pp. 431–441.

    CAS  Google Scholar 

  74. Rumyantsev, E.V., Aleshin, S.N., and Marfin, Yu.S., Russ. J. Phys. Chem. A, 2013, vol. 87, no. 2, p. 326–323. https://doi.org/10.1134/S003602441302026X

    Google Scholar 

  75. Marfin, Yu.S., Merkushev, D.A., Levshanov, G.A., and Rumyantsev, E.V., J. Fluoresc, 2014, vol. 24, no. 6, pp. 1613–1619.

    CAS  PubMed  Google Scholar 

  76. Usol’tsev, S.D., Marfin, Yu.S., and Rumyantsev, E.V, X Konkurs proektov molodykh uchenykh v ramkakh vystavki “Khimiya, khimicheskaya promyshlennost’ i nauka” (X Competition of projects of young scientists in the framework of the exhibition “Chemistry, Chemical Industry, and Science”), Moscow, 2016, pp. 26–27.

    Google Scholar 

  77. Kazak, A., Marfin, Yu, Usoltsev, S., Smirnova, A., Rumyantsev, E., Soldatenko, E., Chumakov, A., Glukhovskoi, E., and Usoltseva, N., Abstract Book AEM2016, Univ. Surrey, 2016, p. 42.

    Google Scholar 

  78. Vodyanova, O.S., Kochergin, B.A., Marfin, Yu.S., and Rumyantsev, E.V, Abstracts of Papers, XIII Mezhdunarodnaya konferentsiya “Spektroskopiya koordinatsionnykh soedinenii” (XIII Int. Conf. “Spectroscopy of Coordination Compounds”), pos. Shepsi, Kuban. Gos. Univ., 2016, pp. 177–178.

    Google Scholar 

  79. Marfin, Yu.S., Rumyantsev, E.V., Usol’tsev, S.D., Molchanov, EYe., Kurzin, VO. et al., Abstracts of Papers, Klaster konferentsii po organicheskoi khimii “OrgKhim-2016” (Cluster Conf. on Organic Chemistry “OrgChem-2016”), St. Petersburg, 2016, p. 389.

    Google Scholar 

  80. Sunahara, H., Urano, Y., Kojima, H., and Nagano, T., J. Am. Chem. Soc, 2007, vol. 129, no. 17, pp. 5597–5604.

    CAS  PubMed  Google Scholar 

  81. Qin, W., Rohand, T., Baruah, M., and Stefan, A., Chem. Phys. Lett., 2006, vol. 420, pp. 562–568.

    CAS  Google Scholar 

  82. Practical Protein Chemistry: A Handbook, Darbre, A. and Waterfield, M.D., Eds., Chichester: Wiley-Blackwell, 1986.

    Google Scholar 

  83. Panteleev, M.A. and Ataullakhanov, F.I., Klin. Onkogematol. Fund. Issled. Klin. Prakt., 2008, vol. 1, pp. 174–181.

    Google Scholar 

  84. Butenas, S. and Mann, K.G, Biokhimiya, 2002, vol. 67, no. 1, pp. 5–15.

    Google Scholar 

  85. Aleksakhina, E.L., Marfin, Yu.S., Merkushev, D.A., Tomilova, I.K., and Rumyantsev, E.V., Kazan. Med. Zh., 2015, vol. 96, no. 5, pp. 792–798.

    Google Scholar 

  86. Bobrov, A.V., Marfin, Yu.S., Kuznetsov, V.V., and Rumyantsev, E.V, Mater. Technol., 2016, pp. 1–8. https://doi.org/10.1080/10667857.2016.1154261.

    Google Scholar 

  87. Bobrov, A.V., Marfin, Yu.S., and Rumyantsev, E.V., Abstracts of Papers, Mezhdunarodnyi molodezhnyi nauchnyi forum “LOMONOSOV-2015” (Int. Youth Scientific Forum “LOMONOSOV-2015”, Moscow, 2015, p. 167.

    Google Scholar 

  88. Merkushev, D.A., Marfin, Yu.S., and Rumyantsev, E.V., Abstracts of papers, XIV Konferentsiia molodykh uchenykh “Aktual’ nye problemy neorganicheskoi khimii” (XIV Conf. of Young Scientists “Actual Problems of Inorganic Chemistry”), Zvenigorod, 2015, p. 164.

    Google Scholar 

  89. Merkushev, D.A., Pushkarev, A.P., Marfin, Yu.S., and Rumyantsev, E.V., Abstracts of Papers, X Vserossiiskaya shkola-konferentsiya molodykh uchenykh “Teoretiches-kaya i eksperimental’ naya khimiya zhidkofaznykh sistem” (Krestovskie chteniya) [X All-Russian School-Conference of Young Scientists “Theoretical and Experimental Chemistry of Liquid-Phase Systems” (Krestov Radings)], Ivanovo, 2015, p. 186.

    Google Scholar 

  90. Merkushev, D.A., Bobrov, A.V., Marfin, Yu.S., and Rumyantsev, E.V., Abstracts of Papers, Mezhdunarodnaya nauchno-tekhnicheskaya konferentsiya “Polimernyye kompozity i tribologiia (Plikomtrib-2015) [Int. Scientific and Technical Conf. “Polymer Composites and Tribology (Pliktribrib-2015)”, Gomel, 2015, p. 54.

    Google Scholar 

  91. Shipalova, M.V., Marfin, Yu.S., and Rumyantsev, E.V., Abstracts of Papers, X Vserossiiskaya shkola-konferen-tsiya molodykh uchenykh “Teoreticheskaya i eksperi-mental’ naya khimiya zhidkofaznykh sistem” (Krestovskie chteniya) [X All-Russian School-Conference of Young Scientists “Theoretical and Experimental Chemistry of Liquid-Phase Systems” (Krestov Radings)], Ivanovo, 2015, p. 68.

    Google Scholar 

  92. Rumyantsev, E.V. and Marfin, Yu.S., Abstracts of Papers, XII Mezhdunarodnaya konferentsiya “Spektroskopiya koordinatsionnykh soedinenii” (XII Int. Conf. “Spe-ktroscopy of Coordination Compounds”, Tuapse, 2015, pp. 86–87.

    Google Scholar 

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Funding

The work was financially supported in part by the Grant of the President of the Russian Federation for support of young Russian candidates of sciences (MK-8835.2016.3) and grants of the Russian Foundation for Basic Research (project nos. 15-33-20002, 15-43-03214, 16-03-01028) and performed using resources of the Center for Collective Use, Ivanovo State University of Chemical Technology.

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Russian Text © The Author(s), 2017, published in Rossiiskii Khimicheskii Zhurnal, 2017, Vol. 61, No. 3, pp. 143–162.

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Rumyantsev, E.V., Marfin, Y.S. Boron Dipirrins: Mechanism of Formation, Spectral and Photophysical Properties, and Directions of Functionalization. Russ J Gen Chem 89, 2682–2699 (2019). https://doi.org/10.1134/S1070363219120454

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