Features of F2-BODIPY synthesis

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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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A. Krasnopyorov

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

编辑信件的主要联系方式.
Email: krasnopyorov13@bk.ru
ORCID iD: 0009-0001-5912-1785
俄罗斯联邦, 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
俄罗斯联邦, 119571, Moscow, prosp. Vernadsky, 86

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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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