Features of F2-BODIPY synthesis

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Аннотация

BODIPY derivatives (4,4-difluoro-4-boron-3a,4a-diaza-S-indacene) due to their high molar extinction coefficients and fluorescence quantum yields and photochemical stability have gained popularity as optical sensors in the field of bioimaging and detection of various analytes. BODIPY molecules differ in substituents not only at the meso-carbon atom, but also at the boron atom. The review article provides information on various approaches to the synthesis of BODIPY derivatives and methods for obtaining “classical” BODIPY, in which the boron atom has 2 fluorine atoms as substituents (F2-BODIPY). The advantages and limitations of synthesis methods are considered, the use of reagents and the frequency of their use are analyzed. Based on literature data, reaction mechanisms for the synthesis of BODIPY derivatives are proposed, attention is paid to the reasons affecting the yield of BODIPY derivatives, including low stability of reagents, the formation of by-products, and the influence of water.

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Авторлар туралы

A. Krasnopyorov

MIREA – Russian Technological University, Institute of fine chemical technologies named after M.V. Lomonosov

Хат алмасуға жауапты Автор.
Email: krasnopyorov13@bk.ru
ORCID iD: 0009-0001-5912-1785
Ресей, 119571, Moscow, prosp. Vernadsky, 86

E. Larkina

MIREA – Russian Technological University, Institute of fine chemical technologies named after M.V. Lomonosov

Email: krasnopyorov13@bk.ru
ORCID iD: 0000-0001-8823-3156
Ресей, 119571, Moscow, prosp. Vernadsky, 86

Әдебиет тізімі

  1. Treibs A., Kreuzer F.-H. Lieb. Ann. 1968, 718 (3), 208–223. doi: 10.1002/jlac.19687180119
  2. Loudet A., Burgess K. Chem. Rev. 2007, 107 (11), 4891–4932. doi: 10.1021/cr078381n
  3. Liu Z., Jiang Z., Yan M., Wang X. Front. Chem. 2019, 7, 712–728. doi: 10.3389/fchem.2019.00712
  4. Arroyo I.J., Hu R., Merino G., Tang B.Z., Pena-Cabrera E. J. Org. Chem. 2009, 74 (15), 5719–5722. doi: 10.1021/jo901014w
  5. Tram K., Yan H., Jenkins H.A., Vassiliev S., Bruce D. Dyes Pigm. 2009, 82 (3), 392–395. doi: 10.1016/j.dyepig.2009.03.001
  6. Uppal T., Bhupathiraju N.V.S.D.K., Vincente M.G.H. Tetrahedron. 2013, 69 (23), 4687–4693. doi: 10.1016/j.tet.2013.03.082
  7. Zhang W., Ahmed A., Cong H., Wang S., Shen Y., Yu B. Dyes Pigm. 2021, 185, 108937–108970. doi: 10.1016/j.dyepig.2020.108937
  8. Kamkaew A., Lim S.H., Lee H.B., Kiew L.V., Chung L.Y., Burgess K. Chem. Soc. Rev. 2013, 42 (1), 77–88. doi: 10.1039/C2CS35216H
  9. Wang L., Ding H., Ran X., Tang H., Cao D. Dyes Pigm. 2020, 172, 107857–107870. doi: 10.1016/j.dyepig.2019.107857
  10. Мартынов В.И., Пахомов А.А. Усп. хим. 2021, 90 (10), 1213–1262 [Martynov V.I., Pakhomov A.A. Russ. Chem. Rev. 2021, 90 (10), 1213–1262] doi: 10.1070/RCR4985
  11. Rezende L. C. D., Emery F. S. Orbital. 2013, 5 (1), 62–83. doi: 10.17807/orbital.v5i1.482
  12. Poddar M., Misra R. Coord. Chem. Rev. 2020, 421, 213462-213484. doi: 10.1016/j.ccr.2020.213462
  13. Boens N., Verbelen B., Dehaen W. Eur. J. Org. Chem. 2015, 2015 (30), 6577-6595. doi: 10.1002/ejoc.201500682
  14. Boens N., Verbelen B., Ortiz M.J., Jiao L., Dehaen W. Coord. Chem. Rev. 2019, 399, 213024–213108. doi: 10.1016/j.ccr.2019.213024
  15. Clarke R.G., Hall M.J. Adv. Heterocycl. Chem. 2019, 128, 181–261. doi: 10.1016/BS.AIHCH.2018.12.001
  16. Loudet A., Burgess K. Handb. Por. Sci. 2010, 8, 1–164. doi: 10.1142/9789814307246_0009
  17. Wories H., Koek J.H., Lodder G., Lugtenburg J. Rec. Trav. Chim. 1985, 104(11), 288–291. doi: 10.1002/recl.19851041104
  18. Wagner R.W., Lindsey J.S. J. Am. Chem. Soc. 1994, 116 (21), 9759–9760. doi: 10.1021/ja00100a055
  19. Wagner R.W., Lindsey J.S. Pure Appl. Chem. 1996, 68 (7), 1373–1380. doi: 10.1351/pac199668071373
  20. Chen J., Burghart A., Derecskei-Kovacs A., Burgess K. J. Org. Chem. 2000, 65 (10), 2900–2906. doi: 10.1021/jo991927o
  21. Li Z., Mintzer E., Bittman R. J. Org. Chem. 2006, 71 (4), 1718–1721. doi: 10.1021/jo052029x
  22. Rothemund P. J. Am. Chem. Soc. 1936, 58 (4), 625–627. doi: 10.1021/ja01295a027
  23. Adler A.D., Longo F.R., Finarelli J.D., Goldmacher J., Assour J., Korsakoff L. J. Org. Chem. 1967, 32 (2), 476. doi: 10.1021/jo01288a053
  24. Lindsey J.S. Metalloporphyrins Catalyzed Oxidations. 1994, 49–86. doi: 10.1007/978-94-017-2247-6_2
  25. Lindsey J.S. Acc. Chem. Res. 2010, 43 (2), 300–311. doi: 10.1021/ar900212t
  26. Arsenault G.P., Bullock E., MacDonald S.F. J. Am. Chem. Soc. 1960, 82 (16), 4384–4389. doi: 10.1021/ja01501a066
  27. Mironov A.F., Evstigneeva R.P. Chem. Heterocycl. Compd. 1976, 12, 249–260. doi: 10.1007/BF00479558
  28. Gossauer A. Reaktivität der Pyrrole. In: Die Chemie der Pyrrole. Berlin: Springer. 1974, 105–167. doi: 10.1007/978-3-642-51118-9_3
  29. Румянцев Е.В., Марфин Ю.С. Росc. хим. ж. 2017, 61 (3), 143-162 [Rumyantsev E.V., Marfin Y.S. Russ. J. Gen. Chem. 2019, 89, 2682–2699] doi: 10.1134/S1070363219120454
  30. Yamada K., Toyota T., Takakura K., Ishimaru M., Sugawara T. New J. Chem. 2001, 25 (5), 667–669. doi: 10.1039/B100757M
  31. Prusty D.K., Kwak M., Wildeman J., Heemann A. Angew. Chem., Int. Ed. 2012, 51 (47), 11894–11898. doi: 10.1002/anie.201206006
  32. Hecht M., Kraus W., Rurack K. Analyst. 2013, 138 (1), 325–332. doi: 10.1039/C2AN35860C
  33. Huang C., Quian Y. Optical Materials. 2019, 92, 53–59. doi: 10.1016/j.optmat.2019.04.012
  34. Chen J., Cui Y., Song K., Liu T., Zhou L., Bao B., Wang R., Wang L. Biomater. Sci. 2021, 9 (6), 2115–2123. doi: 10.1039/D0BM01863E
  35. Porcu P., Vonlanthen M., González-Méndez I., Ruiu A., Rivera E. Molecules. 2018, 23 (9), 2298–2230. doi: 10.3390/molecules23092289
  36. Tekdaş D.A., Viswanathan G., Topal S.Z., Looi C.Y., Wong W.F., Tan G.M.Y., Zorlu Y., Gürek A.G., Lee Y.B., Dumoulin F. Org. Biomol. Chem. 2016, 14 (9), 2665–2670. doi: 10.1039/C5OB02477C
  37. Kubheka G., Mack J., Kobayashi N., Kimura M., Nyokong T. J. Porphyr. Phthalocyanin. 2017, 21, 523–531. doi: 10.1142/S1088424617500511
  38. Molupe N., Babu B., Oluwole D.O., Prinsloo E., Gai L., Shen Z., Mack J., Nyokong T. J. Porphyr. Phthalocyanin. 2020, 24, 973–984. doi: 10.1142/S1088424619501773
  39. Murale D.P., Haque M.M., Hong K.T., Lee J.-S. Bull. Korean Chem. Soc. 2021, 42 (1), 111–114. doi: 10.1002/bkcs.12166
  40. Zou J., Li L., Zhu J., Li X., Yang Z., Huang W., Chen X. Adv. Mater. 2021, 33 (44), 2103627–2103636. doi: 10.1002/adma.202103627
  41. Wang L., Fang G., Cao D. Sens. Actuators B Chem. 2015, 207, 849–857. doi: 10.1016/j.snb.2014.10.110
  42. Pereira N.A.M., Pinho e Melo T.M.V.D. J. Org. Chem. 2014, 46 (3), 183–213. doi: 10.1080/00304948.2014.903140
  43. Dudicˇ M., Lhota´k P., Kra´l V., Lang K., Stibor I. Tetrahedron Lett. 1999, 40 (32), 5949–5952. doi: 10.1016/S0040-4039(99)01181-8
  44. Laha J.K., Dhanalekshmi S., Taniguchi M., Ambroise A., Lindsey J.S. Org. Process Res. Dev. 2003, 7 (6), 799–812. doi: 10.1021/op034083q
  45. Jameson L.P., Dzyuba S.V. Beilstein J. Org. Chem. 2013, 9, 786–790. doi: 10.3762/bjoc.9.89
  46. Amorim V.G., Melo S.M.G., Leite R.F., Coutinho P.A. Dyes Pigm. 2020, 182, 108646–108671. doi: 10.1016/j.dyepig.2020.108646
  47. Hu W., Zhang X.-F., Lu X., Lan S., Tian D., Li T., Wang K., Zhao S., Feng M., Zhang J. J. Lumin. 2018, 194, 185–192. doi: 10.1016/j.jlumin.2017.10.018
  48. Caruso E., Malacarne M. C., Marras E., Papa E., Bertato L., Banfi S., Gariboldi M.B. Bioorg. Med. Chem. 2020, 28 (21), 115737–115746. doi: 10.1016/j.bmc.2020.115737
  49. Agazzi M.L., Ballatore M.B., Durantini A.M., Durantini E.N., Tome A.C. J. Photochem. Photobiol. C 2019, 40, 21–48. doi: 10.1016/j.jphotochemrev.2019.04.001
  50. Gibbs J.H., Robins L.T., Zhou Z., Bobadova-Parvanova P., Cottam M., McCandless G.T., Fronczek F.R., Vicente M.G.H. Bioorg. Med. Chem. 2013, 21 (18), 5770–5781. doi: 10.1016/j.bmc.2013.07.017
  51. Caruso E., Gariboldi M., Sangion A., Gramatica P., Banfi S. J. Photochem. Photobiol. B, Biol. 2017, 167, 269–281. doi: 10.1016/j.jphotobiol.2017.01.012
  52. Gibbs J.H., Zhou Z., Kessel D., Fronczel F.R., Pakhomova S., Vicente M.G.H. J. Photochem. Photobiol. B. Biol. 2015, 145, 35–47. doi: 10.1016/j.jphotobiol.2015.02.006
  53. Caruso E., Banfi S., Barbieri P., Leva B., Orlandi V.T. J. Photochem. Photobiol. B, Biol. 2012, 114, 44–51. doi: 10.1016/j.jphotobiol.2012.05.007
  54. Prasannan D., Raghav D., Sujatha S., Hareendrakrishna Kumar H., Rathinasamy K., Arunkumar C. RSC Adv. 2016, 6(84), 80808–80824. doi: 10.1039/C6RA12258B
  55. Lincoln R., Durantini A.M., Greene L.E., Martinez S.R., Knox R., Becerra M.C., Cosa G. Photochem. Photobiol. Sci. 2017, 16 (2), 178–184. doi: 10.1039/C6PP00166A
  56. Wu W., Guo H., Wu W., Ji S., Zhao J. J. Org. Chem. 2011, 76 (17), 7056–7064. doi: 10.1021/jo200990y
  57. Gao J., Luan T., Lv J., Yang M., Li H., Yuan Z. J. Photochem. Photobiol. B, Biol. 2023, 241, 112666. doi: 10.1016/j.jphotobiol.2023.112666
  58. Ashokkumar P., Weißhoff H., Kraus W., Rurack K. Angew. Chem., Int. Ed. 2014, 53 (8), 2225–229. doi: 10.1002/anie.201307848
  59. Wang J., Hou Y., Li C., Zhang B., Wang X. Sens. Actuators B Chem. 2011, 157 (2), 586–593. doi: 10.1016/j.snb.2011.05.027
  60. Li Q., Guo Y., Chen Y. Indian J. Chem. 2018, 57, 186–191. http://nopr.niscpr.res.in/handle/123456789/43625
  61. Dixit S., Agarwal N. J. Photochem. Photobiol. A 2017, 345, 66–71. doi: 10.1016/j.jphotochem.2017.04.018
  62. Yu Y., Shu T., Yu B., Deng Y., Fu C., Gao Y., Dong C., Ruan Y. Sens. Actuators B Chem. 2018, 255, 3170–3178. doi: 10.1016/j.snb.2017.09.142
  63. Wang L., Li L., Cao D. Sens. Actuators B Chem. 2017, 239, 1307–1317. doi: 10.1016/j.snb.2016.09.112
  64. Fu C., Wang Z., Rao C., Li Z., Chen L., Zhu T., Yi F., Yao Z.-J., Liu C. Dyes Pigm. 2019, 170, 107598–107604. doi: 10.1016/j.dyepig.2019.107598
  65. Soni D., Duvva N., Badgurjar D., Roy T.K., Nimesh S., Arya G., Giribabu L., Chitta R. Chem. Asian. J. 2018, 13, 1594–1608. doi: 10.1002/asia.201800349
  66. Wang C., Qian Y. J. Lumin. 2019, 210, 261–268. doi: 10.1016/j.jlumin.2019.02.044
  67. Kang J., Huo F., Zhang Y., Chao J. Sens. Actuators B Chem. 2018, 273, 1532–1538. doi: 10.1016/j.snb.2018.07.072
  68. Kumar B., Saraf P., Sarkar M., Kumar D. Tetrahedron. 2023, 137, 133380. doi: 10.1016/j.tet.2023.133380
  69. Treibs A., Reitsam F. Lieb. Ann. 1958, 611 (1), 194–205. doi: 10.1002/jlac.19586110118
  70. Treibs A., Reitsam F. Lieb. Ann. 1958. 611 (1), 205–223. doi: 10.1002/jlac.19586110119
  71. Strandheim K.O. In: Synthesis and Characterization of BODIPY Dyes for Optoelectronic Application. NTNU. 2019. https://ntnuopen.ntnu.no/ntnu-xmlui/handle/11250/2634477
  72. Badon I.W., Lee J., Vales T.P., Cho B.K., Kim H.-J. J. Photochem. Photobiol. A 2019, 377, 214–219. doi: 10.1016/j.jphotochem.2019.03.050
  73. Pakhomov A.A., Kononevich Y.N., Stukalova M.V., Svidchenko E.A., Surin N.M., Cherkaev G.V., Shchegolikhina O.I., Martynov V.I., Muzafarov A.M. Tetrahedron Lett. 2016, 57 (9), 979–982. doi: 10.1016/j.tetlet.2016.01.059
  74. Pakhomov A.A., Deyev I.E., Ratnikova N.M., Chumakov S.P., Mironiuk V.B., Kononevich Y.N., Muzafarov A.M., Martynov V.I. Biotechniques. 2017, 63 (2), 77–80. doi: 10.2144/000114577
  75. Lin H.-Y., Huang W.-C., Chen Y.-C., Chou H.-H., Hsu C.-Y., Lin J.T., Lin H.-W. Chem. Commun. 2012, 48 (71), 8913–9815. doi: 10.1039/C2CC34286C
  76. Kaplan N., Taşcı E., Emrullahoğlu M., Gökce H., Tuğluoğlu N., Eymur S. J. Mater. Sci. Mater. Electron. 2021, 32 (12), 16739–16747. doi: 10.1007/s10854-021-06231-8
  77. Wu L., Burgess K. Chem. Commun. 2008, 40, 4933–4935. doi: 10.1039/b810503k
  78. Jiao L., Yu C., Liu M., Wu Y., Cong K., Meng K., Wang Y., Hao E. J. Org. Chem. 2010, 75 (17), 6035–6038. doi: 10.1021/jo101164a
  79. Netz N., Diez-Poza C., Barbero A., Opatz T. Eur. J. Org. Chem. 2017, 31, 4580–4599. doi: 10.1002/ejoc.201700773
  80. Kim K., Kwon H., Choi D., Lim T., Min L., Son S.-H., Byun Y. Bioorg. Chem. 2019, 89, 102990–102999. doi: 10.1016/j.bioorg.2019.102990
  81. Zhang X.-F., Zhang G.O., Zhu J. J. Fluoresc. 2019, 29 (2), 407–416. doi: 10.1007/s10895-019-02349-5
  82. Arellano-Reyes R.A., Prabhakaran A., Sia R.C.E., Guthmuller J., Jha K.K., Yang T., Dietzek-Ivanšić B., McKee V., Keyes T.E. Chem. Eur. J. Chem. 2023, 29 (24). doi: 10.1002/chem.202300239
  83. Srinivasan Y., Guzikowski A.P., Haugland R.P., Angelides K.J. J. Neurosci. 1990, 10 (3), 985–995. doi: 10.1523/JNEUROSCI.10-03-00985.1990
  84. Barton A.C., Kang H.C., Rinaudo M.S., Monsma F.J. Jr., Stewart-Fram R.M., Macinko J.A. Jr., Haugland R.P., Ariano M.A., Siblley D.R. Brain Res. 1991, 547 (2), 199–207. doi: 10.1016/0006-8993(91)90963-V
  85. Ariano M.A., Kang H.C., Haugland R.P., Sibley D.R. Brain Res. 1991, 547 (2), 208–222. doi: 10.1016/0006-8993(91)90964-w
  86. Freindorf M., Kraka E. Catalysts. 2022, 12 (4), 415–446. doi: 10.3390/catal12040415
  87. Cornel V., Lovely C.J. EROS, 2007, 1–16. doi: 10.1002/9780470842898.rb249.pub2
  88. Thivierge C., Han J., Jenkins R.M. Burgess K. J. Org. Chem. 2011, 76 (13), 5219–5228. doi: 10.1021/jo2005654
  89. Белобрицкая Е.Е, Неунылова М.В., Василисков В.А., Румянцева В.Д., Чудинов А.В., Заседателев А.С. Биоорг. хим. 2007, 33 (6), 664-666 [Belobritskaya E.E, Neunylova M.V., Vasiliskov V.A., Rumiantseva V.D., Chudinov A.V., Zasedatelev A.S. Russ. J. Bioorg. Chem. 2007, 33 (6), 617–619] doi: 10.1134/S1068162007060155
  90. Gupta R.R., Kumar M., Gupta V. Heterocyclic Chemistry. Berlin: Springer, 1999, 3–179. doi: 10.1007/978-3-662-07757-3_2
  91. Kanazawa K.K., Diaz A.F., Geiss R.H., Gill W.D., Kwak J.F., Logan J.A., Rabolt J.F., Street G.B. J. Chem. Soc., Chem. Commun. 1979, 19, 854–855. doi: 10.1039/C39790000854
  92. Lee C.-H., Lindsey J.S. Tetrahedron. 1994, 50 (39), 11427–11440. doi: 10.1016/S0040-4020(01)89282-6
  93. Littler B.J., Miller M.A., Hung C.-H., Wagner R.W., O'Shea D.F., Boyle P.D., Lindsey J.S. J. Org. Chem. 1999, 64 (4), 1391–1396. doi: 10.1021/jo982015+
  94. Cadby A.J., Yang C., Holdcoft S., Bradley D.D.C., Lane P.A. Adv. Mater. 2002, 14 (1), 57–60. doi: 10.1002/1521-4095(20020104)14:1<57::AID-ADMA57>3.0.CO;2-0
  95. Thomas R., Durix S., Sinturel C., Omonov T., Goossens S., Groeninckx G., Moldenaers P., Thomas S. Polymer. 2007, 48 (6), 1695–1710. doi: 10.1016/j.polymer.2007.01.018
  96. Tan Y., Ghandi K. Synth. Met. 2013, 175, 183–191. doi: 10.1016/j.synthmet.2013.05.014
  97. Singh R.S., Paitandi R.P., Gupta R.K., Pandey D.S. Coord. Chem. Rev. 2020, 414, 213269–213321. doi: 10.1016/j.ccr.2020.213269
  98. Maruthapandi M., Gedanken A. Polymers. 2019, 11 (8), 1240–1255. doi: 10.3390/polym11081240
  99. Chen J., Burghart A., Wan C.-W., Thai L., Ortiz C., Reibenspies J., Burgess K. Tetrahedron Lett. 2000, 41 (14), 2303–2307. doi: 10.1016/S0040-4039(00)00166-0
  100. Bröring M., Krüger R., Kleeberg C. Z. Anorg. Allg. Chem. 2008, 634 (9), 1555–1559. doi: 10.1002/zaac.200800112
  101. Benniston A.C., Sirbu D., Turta C., Probert M.R., Clegg W. Eur. J. Inorg. Chem. 2014, 2014 (36), 6212–6219. doi: 10.1002/ejic.201402752
  102. Li T., Gu W., Yu C., Lv X., Wang H., Hao E., Jiao L. Chinese J. Chem. 2016, 34 (10), 989–996. doi: 10.1002/cjoc.201600500
  103. Banerjee A.K., Maldonado A., Arrieche D.A., Bedoya L., Vera W.J., Cabrea E.V., Poon P.S. Bioorg. Org. Chem. 2019, 3 (1), 1–9. doi: 10.15406/mojboc.2019.03.00090
  104. Wamser C.A. J. Am. Chem. Soc. 1951, 73 (1), 409–416. doi: 10.1021/ja01145a134
  105. Lundrigan T., Cameron T.S., Thompson A. Chem. Commun. 2014, 50 (53), 7028–7031. doi: 10.1039/C4CC02706J
  106. Beh M.H.R., Douglas K.I.B., House K.T.E., Murphy A.C., Sinclair J.S.T., Thompson A. Org. Biomol. Chem. 2016, 14, 11473–11479. doi: 10.1039/C6OB02238C

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2. Fig. 1. Structure of BODIPY derivatives. Substituents (R) can be the same or different.

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3. Fig. 2. Structures of different BODIPY subclasses. Substituents around the indacene core (R) may be the same or different.

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4. Fig. 3. Structure of fully unsubstituted BODIPY

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5. Fig. 4. Polypyrroles. a) Main polymerization product; b) Structures of bonds inside polypyrroles: (1) α,α'-bonds, (2) α,β'-bonds, (3) β,β'-bonds; * – place of attachment of bonds to the polypyrrole chain

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6. Fig. 5. Structures of various pyrrole products. Substituents (R) may be the same or different.

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7. Fig. 6. Structure of pyrroloindolizines. Substituents (R1–R4) can be the same or different.

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8. Fig. 7. Structures of dipyrrolylmethenes: (1) αα'-dipyrrolylmethene, (2) αβ'-dipyrrolylmethene, (3) ββ'-dipyrrolylmethene. Substituents (R, R1, R2) can be the same or different.

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9. Fig. 8. Structure of copolymers of pyrrole and aniline

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10. Fig. 9. Structure of difluoropyrrolooxaboroles. Substituents (R1-R4) can be the same or different.

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11. Scheme 1. Stages of BODIPY synthesis

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12. Scheme 2. Synthesis of BODIPY derivatives from pyrroles and benzaldehydes. Substituents (R, R1-R3) can be the same or different

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13. Scheme 3. Proposed mechanism of formation of BODIPY derivatives from pyrroles and benzaldehydes based on [18, 19, 28, 29]

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14. Scheme 4. Synthesis of BODIPY derivatives from pyrroles and acid chlorides. Substituents (R, R1-R3) can be the same or different

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15. Scheme 5. Proposed mechanism of formation of BODIPY derivatives from pyrroles and acid chlorides based on [28, 29, 71]

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16. Scheme 6. Synthesis of BODIPY derivatives from α-unsubstituted pyrroles and 2-ketopyrroles. Substituents (R, R1-R6) can be the same or different

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17. Scheme 7. Synthesis of BODIPY derivatives from 2 pyrrole-2-carbaldehydes. Substituents (R1-R3) can be the same or different

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18. Scheme 8. Proposed mechanism of formation of BODIPY derivatives from α-unsubstituted pyrroles and 2-ketopyrroles based on [28, 29, 77]

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19. Scheme 9. Synthesis of BODIPY derivatives from pyrroles and diacid anhydrides. Substituents (R1-R3) can be the same or different

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20. Scheme 10. Proposed mechanism of formation of BODIPY derivatives from pyrroles and diacid anhydrides based on [28, 29, 86, 87]

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21. Scheme 11. Dynamic equilibrium of BF3OEt2

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22. Scheme 12. Formation of dipyrrolylmethene tetrafluoroborate. Substituents (R, R1, R2) can be the same or different

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23. Scheme 13. “Rescue” of the reaction. Substituents (R, R1, R2) can be the same or different

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24. Table 1. Fig. 1

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