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A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Science, 664033 Irkutsk, Russia
Author to whom correspondence should be addressed.
Molbank 2023, 2023(1), M1595;
Submission received: 31 January 2023 / Revised: 17 February 2023 / Accepted: 20 February 2023 / Published: 23 February 2023


The title compound, 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(2-naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1), was synthesized for the first time in a 62% yield by the P2O5-promoted condensation of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]-ethan-1-ol (2) with 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3) followed by the oxidation of dipyrromethane 4 and the complexation of dipyrromethene thus formed with BF3. The product fluoresces in a long wave region (651–662 nm) with a high quantum yield (0.49–0.61).

1. Introduction

Bright fluorescent dyes with a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene core, known as BODIPY dyes, are of extreme importance for materials science and have gained much attention over the last few years [1,2]. The unique combination of photo- and thermal stability, high quantum yield and easy absorption/emission wavelength tuning from UV–vis to near IR region make BODIPY derivatives suitable for application as chemosensors for organic and inorganic targets, OLEDs, nonlinear optics, dye lasers, perovskite- and dye-sensitized solar cell, semiconductors [3], etc. The low cytotoxicity, stability in physiological media and absorption/emission in NIR region allows wide bioapplications of BODIPY fluorophores as in vitro or in vivo probes, fluorescent labels of proteins, lipids, DNA, staining agents for lifetime cell observations or for biochemical investigations, e.g., in antibacterial or anticancer developments [4,5].
The nature of the BODIPY core unit provides HOMO–LUMO electron transitions under external irradiation and eventually fluorescent properties of a dye molecule. However, specific wavelength values of absorption and emission are determined by the structure of functional substituents in the pyrrole counterparts and at a methylene spacer. One of the most common ways to modulate the properties of the BODIPY fluorophore is to extend the conjugation chain by the introduction of various aryl or heterocyclic substituents at the 3- and 5-positions of the BODIPY core [6,7]. Additionally, it is known that the replacement of the usual alkyl- or aromatic substituents in the meso-position of the BODIPY core by strong electron-withdrawing fluorinated ones results in a deep bathochromic shift to the red region, the radiation in which has better tissue penetration and less photodamage [8,9,10,11,12]. The introduction of isoxazole scaffolds [13,14], which exhibit a wide spectrum of targets and broad biological activities, to the molecule can provide additional benefits for fluorophore.

2. Results

We have shown that 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1), fluorescing in a long wave region (662 nm) with a high quantum yield (0.61), can be obtained according to our previously developed methodology [9] by the P2O5-promoted condensation of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]ethan-1-ol (2) with 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3) (CH2Cl2, rt, 20 h) followed by the oxidation of dipyrromethane 4 and the complexation of dipyrromethene thus formed with BF3 in the presence of diisopropylethylamine at room temperature for 1.5 h (Scheme 1). The last two stages are realized as a one-pot procedure to furnish the target fluorophore BODIPY 1 in a 62% yield.
2,2,2-Trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]ethan-1-ol (2) and 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3), required for the synthesis of fluorophore 1, were obtained, by the reduction of easily available [15] 5-(naphthalen-2-yl)-2,2,2-trifuoroacetylpyrrole with NaBH4 (Scheme 2a) (methanol, rt, 1 h) and the reaction of 2-benzoylethynylpyrrole with NH2OH (Scheme 2b), respectively [16].
The compound 1 in n-hexane, CH2Cl2, THF, and ethylacetate fluoresces with high quantum yields (ΦF 0.49–0.70); it has a nanosecond fluorescence life-time (τ), typical for BODIPY molecules. Alternatively, this fluorophore exhibits only weak fluorescence in MeCN, whereas fluorescence life-time in this solvent was very short. The spectroscopic and photophysical characteristics of fluorophore 1, including the positions of the maxima of the absorption (λabs) and fluorescence (λfl) bands, fluorescence quantum yields (ΦF), and life-time (τ) in different solvents are shown in Table 1. Normalized absorption and fluorescence spectra of compound 1 in different solvents are given in the SM (Figure S11).
The structure and composition of synthesized compound 1 were confirmed by 1H, 13C, 19F, 11B NMR, and IR spectroscopy (see Supplementary Materials). Elemental analysis established the chemical formula of compound 1.
Thus, we have synthesized 4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1), a new BODIPY fluorophore with an extended conjugation chain by the introduction of naphthyl and 3-phenylisoxazolyl substituents, which fluoresces intensively in a long wavelength region. The introduction of a pharmacologically valuable isoxazole scaffold to molecule of fluorophore 1 significantly expands its application area.

3. Materials and Methods

General. NMR spectra were recorded on a Bruker DPX-400 spectrometer (Bruker, Billerica, MA, USA) (400.13 MHz for 1H, 100.6 MHz for 13C, 376.5 MHz for 19F, 40.5 MHz for 15N and 128.4 MHz for 11B) in CDCl3 or DMSO-d6. The internal standards were the residual solvent signals 7.27 ppm for 1H and 77.1 ppm for 13C (CDCl3), 2.50 ppm for 1H and 39.5 ppm for 13C (DMSO-d6). The 19F chemical shifts were referenced to CFCl3. Coupling constants (J) were measured from one-dimensional spectra, and multiplicities were abbreviated as follows: s (singlet), br. s (broad singlet), d (doublet), t (triplet), q (quartet) and m (multiplet). The assignment of signals in the 1H NMR spectra was made using COSY and NOESY experiments. Resonance signals of carbon atoms were assigned based on 1H-13C HSQC and 1H-13C HMBC experiments. The values of the δ 15N were measured through the 2D 1H-15N HMBC experiment. The 15N chemical shifts were referenced to CH3NO2.
IR spectra were recorded on a two-beam Bruker Vertex 70 spectrometer (Bruker, Billerica, MA, USA), in a film. UV–vis absorption spectra were recorded on a Hitachi U-3010 (Hitachi High-Tech, Japan) spectrophotometer. Fluorescence spectra were recorded on a Hitachi F-4500 (Hitachi High-Technologies, Tokyo, Japan) fluorescence spectrophotometer. Elemental analyses (C, H, N) were performed on an EA FLASH 1112 Series (CHN Analyzer) instrument (Thermo Finnigan, Rodano, Italy). Fluorine content was determined on a SPECOL 11 (Carl Zeiss Jena, Jena, Germany) spectrophotometer. Melting points (uncorrected) were measured using a Stuart Scientific melting point SMP3 apparatus.
4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1). The mixture of 3-phenyl-5-(5-{2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]ethyl}-1H-pyrrol-2-yl)-isoxazole (4) (1.934 g, 4.0 mmol) and DDQ (0.908 g, 4.0 mmol) in CH2Cl2 (70 mL) was stirred at room temperature for 1.5 h. DIPEA (5.170 g, 40.0 mmol) was added and the mixture was stirred for 15 min, then BF3.OEt2 (6.813 g, 48.0 mmol) was added dropwise. The mixture was stirred for 1.5 h, then ~2/3 of solvent was removed under a vacuum and the obtained residue was purified by column chromatography (SiO2, eluent n-hexane/CH2Cl2, gradient 1:0 → 0:1) to afford compound 1 (1.313 g, 62%) as dark blue crystals, mp 211–212 °C. IR spectrum (film) ν, cm−1: 1625, 1566, 1494, 1444, 1411, 1394, 1345, 1300, 1277, 1248, 1225, 1140, 1140, 1111, 1088, 1052. 1H NMR (400.13 MHz, CDCl3) δ: 8.57 (s, 1H, naphthyl), 8.12–8.09 (m, 1H, naphthyl), 8.02–8.00 (m, 2H, naphthyl), 7.96–7.94 (m, 1H, naphthyl), 7.87–7.85 (m, 2H, Ho, Ph), 7.64–7.59 (m, 3H, H-7, H-4 oxazole, naphthyl), 7.56 (s, 1H, naphthyl), 7.47–7.45 (m, 4H, H-1, Hm, p, Ph), 7.29 (d, J = 4.5 Hz, 1H, H-2), 7.03 (d, J = 4.5 Hz, 1H, H-6). 13C NMR (100.6 MHz, CDCl3) δ: 165.8, 163.7, 161.4, 142.9, 136.1, 134.6, 133.2, 132.9, 132.5, 131.3 (t, J = 4.38 Hz), 130.2, 129.5, 129.0 (2C), 128.8, 128.7, 128.6, 128.5, 128.4, 127.9, 127.1 (2C), 127.0, 126.2 (t, J = 4.72 Hz), 125.7, 123.9, 122.5 (q, J = 276.0 Hz, CF3), 121.1, 105.5 (t, J = 9.2 Hz). 15N NMR (40.5 MHz, CDCl3) δ: −200.1 (N-3a), −192.6 (N-4a), −7.9 (NO). 19F NMR (376.5 MHz, CDCl3) δ: −137.1 (m, BF2), −54.9 (CF3). 11B NMR (128.4 MHz, CDCl3) δ: 1.1 (t, J = 30.9 Hz, BF2). Found, %: C, 65.61; H, 3.42; F, 18.05; N, 7.68. C29H17BF5N3O (529.28). Calcd, %: C, 65.81; H, 3.24; B, 2.04; F, 17.95; N, 7.94; O, 3.02.
3-Phenyl-5-(5-{2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]-ethyl}-1H-pyrrol-2-yl)isoxazole (4). The mixture of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]ethan-1-ol (2) (1.456 g, 5.0 mmol), 3-phenyl-5-(1H-pyrrol-2-yl)ioxazole (3) (1.051 g, 5.0 mmol) and P2O5 (0.780 g, 5.5 mmol) in CH2Cl2 (50 mL) was stirred at room temperature for 20 h. Then, the mixture was diluted with a saturated solution of NaHCO3 (50 mL). The organic layer was separated, and an aqueous layer was extracted with CH2Cl2 (2 × 20 mL). The combined organic layers were washed with water (3 × 30 mL) and dried over CaCl2. After removing the solvent, 2.248 g (93%) of compound 4 was obtained as a dark rose solid, mp 104–106 °C. IR spectrum (film) ν, cm−1: 3422, 3274, 3058, 3012, 2926, 1699, 1684, 1627, 1559, 1511, 1456, 1400, 1256, 1190, 1162, 1108, 1042. 1H NMR (400.13 MHz, DMSO-d6) δ: 12.10 (br. s, 1H, NH), 11.60 (br. s, 1H, NH), 8.12 (s, 1H, naphthyl), 7.91–7.81 (m, 6H, Ph, naphthyl), 7.54–7.48 (m, 4H, Ph, naphthyl), 7.45–7.42 (m, 1H, Hp, Ph), 7.12 (s, 1H, H-4, oxazole), 6.73–6.72 (m, 1H, H-4′), 6.68–6.66 (m, 1H, H-3), 6.40–6.38 (m, 1H, H-3′), 6.31–6.30 (m, 1H, H-4), 5.19 (q, J = 9.6 Hz, 1H, CH). 13C NMR (100.6 MHz, DMSO-d6) δ: 164.0, 162.1, 133.4, 131.6, 131.5, 130.2, 129.9, 129.1 (2C), 128.6, 128.2, 128.0, 127.6, 127.4, 126.5, 126.47 (2C), 125.21, 125.20, 125.15 (q, J = 279.5 Hz, CF3), 123.1, 120.5, 119.8, 110.1, 110.06, 109.7, 107.0, 95.2, 41.9 (q, J = 29.7 Hz, CH). 19F NMR (376.5 MHz, CDCl3) δ −67.9 (m, J = 8.58 Hz, CF3). Found, %: C, 72.22; H, 4.09; F, 11.92; N, 8.52. C29H20F3N3O (483.49). Calcd, %: C, 72.04; H, 4.17; F, 11.79; N, 8.69; O, 3.31.
2,2,2-Trifluoro-1-[5-(naphthalen-2-yl)pyrrol-2-yl]ethan-1-ol (2). To the mixture of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)pyrrol-2-yl]ethanone (2.347 g, 8.2 mmol) and NaHCO3 (1.447 g, 17.2 mmol, 2.1 equiv.) in MeOH (65 mL) NaBH4 (0.620 g, 16.4 mmol) was added in portions with 10 min of intensive stirring (room temperature). The mixture was stirred for 50 min. The residue, after removing MeOH, was diluted with water (3 mL), extracted with diethyl ether (4 × 10 mL) and dried over Na2SO4. After removing the solvent, compound 2 was obtained as a beige solid (2.265 g, 95%), mp 132–134 °C. IR spectrum (film), ν, cm−1: 3421, 3057, 3024, 2928, 1700, 1684, 1629, 1605,1509, 1504, 1457, 1405, 1385, 1362, 1269, 1210, 1174, 1124, 1042. 1H NMR (400.13 MHz, CDCl3) δ: 8.95 (br. s, 1H, NH), 7.89–7.81 (m, 4H, naphthyl), 7.68–7.66 (m, 1H, naphthyl), 7.52–7.44 (m, 2H, naphthyl), 6.62–6.61 (m, 1H, H-4), 6.61–6.40 (m, 1H, H-3), 5.18 (q, J = 6.6 Hz, CHCF3), 3.12 (br. s, 1H, OH). 13C NMR (100.6 MHz, DMSO-d6) δ: 133.5, 131.7, 131.5, 130.0, 128.2, 127.9, 127.7, 127.6, 126.5, 124.8 (q, J = 282.3 Hz, CF3), 125.3, 123.2, 120.7, 109.0, 106.9, 65.9 (q, J = 32.3 Hz, C-OH). 15N NMR (40.5 MHz, CDCl3) δ: −240.5 (NH). 19F NMR (376.5 MHz, CDCl3) δ: −78.3 (d, J = 6.6 Hz, CF3). Found, %: C, 66.11; H, 4.01; F, 19.39; N, 4.99. C16H12F3NO (291.27). Calcd, %: C, 65.98; H, 4.15; F, 19.57; N, 4.81; O, 5.49.
3-Phenyl-5-(pyrrol-2-yl)isoxazole (3). A solution of NH2OH∙HCl (2.088 g, 30.0 mmol) in H2O (5 mL) was added to a solution of NaOH (1.80 g, 45.0 mmol) in H2O (5 mL). This was added to a solution of 2-benzoylethynylpyrrole (0.585 g, 3.0 mmol) in DMSO (50 mL) and the reaction mixture was stirred at 45–50 °C for 4 h. The reaction mixture was cooled to room temperature and poured into brine, residue filtered off, washed with water and dried, giving pure isoxazole 3 (0.524 g, 83%) as light yellow crystals, mp 123–125 °C. Spectral characteristics of isoxazole 3 correspond to the literature data [16].

Supplementary Materials

The followings can be downloaded online. Copies of 1H NMR, 13C, 19F, 11B NMR. Normalized absorption and fluorescence spectra of compound 1.

Author Contributions

Conceptualization, B.A.T. and L.N.S.; methodology, E.F.S., O.V.P. and D.N.T., preparation of compounds, E.F.S., O.V.P. and D.N.T., formal analysis, I.A.U.; data curation, L.N.S.; writing—original draft preparation, L.N.S., O.V.P. and D.N.T.; writing—review and editing, O.V.P., E.F.S., I.A.U. and L.N.S.; supervision, Boris A. Trofimov. All authors have read and agreed to the published version of the manuscript.


This research was funding by the Ministry of Education and Science of Russian Federation (State Registration No. 121021000199-6).

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.


The authors thank the Baikal Analytical Centre of collective use.

Conflicts of Interest

The authors declare no conflict of interest.


  1. Lu, H.; Shen, Z. BODIPYs and Their Derivatives: The Past, Present and Future. Front. Chem. 2020, 8, 290. [Google Scholar] [CrossRef] [PubMed]
  2. Gurubasavaraj, P.M.; Sajjan, V.P.; Muñoz-Flores, B.M.; Jiménez Pérez, V.M.; Hosmane, N.S. Recent Advances in BODIPY Compounds: Synthetic Methods, Optical and Nonlinear Optical Properties, and Their Medical Applications. Molecules 2022, 27, 1877. [Google Scholar] [CrossRef] [PubMed]
  3. Poddar, M.; Misra, R. Recent advances of BODIPY based derivatives for optoelectronic applications. Coord. Chem. Rev. 2020, 421, 213462. [Google Scholar] [CrossRef]
  4. Shi, Z.; Han, X.; Hu, W.; Bai, H.; Peng, B.; Ji, L.; Fan, Q.; Li, L.; Huang, W. Bioapplications of small molecule Aza-BODIPY: From rational structural design to in vivo investigations. Chem. Soc. Rev. 2020, 49, 7533–7567. [Google Scholar] [CrossRef] [PubMed]
  5. Kaur, P.; Singh, K. Recent advances in the application of BODIPY in bioimaging and chemosensing. J. Mater. Chem. C 2019, 7, 11361–11405. [Google Scholar] [CrossRef]
  6. Loudet, A.; Burgess, K. BODIPY Dyes and Their Derivatives:  Syntheses and Spectroscopic Properties. Chem. Rev. 2007, 107, 4891–4932. [Google Scholar] [CrossRef] [PubMed]
  7. Ulrich, G.; Ziessel, R.; Harriman, A. The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed. Angew. Chem. Int. Ed. 2008, 47, 1184–1201. [Google Scholar] [CrossRef] [PubMed]
  8. Li, L.; Nguyen, B.; Burgess, K. Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core. Bioorg. Med. Chem. Lett. 2008, 18, 3112–3116. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  9. Sobenina, L.N.; Vasil’tsov, A.M.; Petrova, O.V.; Petrushenko, K.B.; Ushakov, I.A.; Clavier, G.; Meallet-Renault, R.; Mikhaleva, A.I.; Trofimov, B.A. General Route to Symmetric and Asymmetric meso-CF3-3(5)-Aryl(hetaryl)- and 3,5-Diaryl(dihetaryl)-BODIPY Dyes. Org. Lett. 2011, 13, 2524–2527. [Google Scholar] [CrossRef] [PubMed]
  10. Choi, S.; Bouffard, J.; Kim, Y. Aggregation-induced emission enhancement of a meso-trifluoromethyl BODIPY via J-aggregation. Chem. Sci. 2014, 5, 751–755. [Google Scholar] [CrossRef]
  11. Ray, C.; Banuelos, J.; Arbeloa, T.; Maroto, B.L.; Moreno, F.; Agarrabeitia, A.R.; Ortiz, M.J.; Lopez-Arbeloa, I.; de la Moya, S. Push-pull flexibly-bridged bis(haloBODIPYs): Solvent and spacer switchable red emission. Dalton Trans. 2016, 45, 11839–11848. [Google Scholar] [CrossRef] [PubMed]
  12. Jiang, X.-D.; Fang, T.; Liu, X.; Xi, D. Synthesis of meso-CF3-Substituted BODIPY Compounds with Redshifted Absorption. Eur. J. Org. Chem. 2017, 2017, 5074–5079. [Google Scholar] [CrossRef]
  13. Zhu, J.; Mo, J.; Lin, H.-Z.; Chen, Y.; Sun, H.-P. The recent progress of isoxazole in medicinal chemistry. Bioorg. Med. Chem. 2018, 26, 3065–3075. [Google Scholar] [CrossRef] [PubMed]
  14. Pandhurnekar, C.P.; Pandhurnekar, H.C.; Mungole, A.J.; Butoliya, S.S.; Yadao, B.G. A review of recent synthetic strategies and biological activities of isoxazole. J. Heterocycl. Chem. 2022, 1, 1–29. [Google Scholar] [CrossRef]
  15. Korostova, S.E.; Mikhaleva, A.I.; Sobenina, L.N.; Shevchenko, S.G.; Sigalov, M.V.; Karataeva, I.M.; Trofimov, B.A. Pyrroles from ketoximes and acetylene. Chem. Heterocycl. Compd. 1989, 25, 39–43. [Google Scholar] [CrossRef]
  16. Tomilin, D.N.; Sobenina, L.N.; Petrushenko, K.B.; Ushakov, I.A.; Trofimov, B.A. Design of novel meso-CF3-BODIPY dyes with isoxazole substituents. Dyes Pigm. 2018, 152, 14–18. [Google Scholar] [CrossRef]
Scheme 1. Synthesis of 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalene-2-yl)-4-bora-3a,4a-diaza-s-indacene (1).
Scheme 1. Synthesis of 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalene-2-yl)-4-bora-3a,4a-diaza-s-indacene (1).
Molbank 2023 m1595 sch001
Scheme 2. Synthesis of precursors of 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1): (a) synthesis of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]ethan-1-ol (2); (b) synthesis of 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3).
Scheme 2. Synthesis of precursors of 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1): (a) synthesis of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]ethan-1-ol (2); (b) synthesis of 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3).
Molbank 2023 m1595 sch002
Table 1. Spectroscopic and photophysical characteristics of compound 1 in different solvents.
Table 1. Spectroscopic and photophysical characteristics of compound 1 in different solvents.
BODIPYSolventλabs., nmλfl., nmΦFτ/ns
Molbank 2023 m1595 i001n-hexane6146510.706.2
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MDPI and ACS Style

Sagitova, E.F.; Petrova, O.V.; Tomilin, D.N.; Ushakov, I.A.; Sobenina, L.N.; Trofimov, B.A. 4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene. Molbank 2023, 2023, M1595.

AMA Style

Sagitova EF, Petrova OV, Tomilin DN, Ushakov IA, Sobenina LN, Trofimov BA. 4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene. Molbank. 2023; 2023(1):M1595.

Chicago/Turabian Style

Sagitova, Elena F., Olga V. Petrova, Denis N. Tomilin, Igor A. Ushakov, Lyubov N. Sobenina, and Boris A. Trofimov. 2023. "4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene" Molbank 2023, no. 1: M1595.

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