Laboratory of Functional Materials Synthesis

The laboratory is conducting an NCN Opus 17 project, entitled: “The phospho-Friedel-Crafts/Bradsher reaction- a new member of the heteroatom family”.

Contract No. UMO-2019/33/B/ST4/02843.
Head: Prof. Dr. Piotr Balczewski.
Grant realized from 28.02.2020 to 27.02.2024.

Short description

Research interests:

• organic and heteroorganic chemistry (P, S, N, Si, B);
• new concepts in organic chemistry;
• chemistry of materials (synthesis and properties of optoelectronic materials based on small  organic molecules);
• synthesis of natural products and biologically active compounds (cyclopentanoids, lignanoids, alkaloids, biologically active quaternary heteronium salts, including optically active ionic liquids, bio-dendrimers);
• studies on reactions involving reactive intermediates (carbocations – S_EAr, carbanions, carbon-centered radicals at the phosphorus atom; reaction mechanisms);
• sonochemistry;
• ecotoxicological and agricultural chemistry (studies on the eco(phyto)toxic properties of organic compounds, including drugs as well as studies on herbicidal properties of new heteroorganic compounds,
• pharmaceutical chemistry (improvement of bioavailability of antihypertensive drugs, drugs against COVID 19).

The studies are carried out in cooperation with the Structural and Material Research Laboratory (PB) at the JDU, in Częstochowa.

Antiviral polyanionic dendrimer (Na-salt) against both types of HIV

Recent scientific achievements:
1. Discovery of two, new hetero variants of the-Friedel-Crafts/Bradsher reaction, as an oxygen (oxo-F-C/B)^1-6 and sulfur variant (thio-F-C/B).^6,7

Meaning: These reactions lead to the formation of unique RO- and RS-substituted (hetero) acenes characterized by: 1) high degree of substitution, 2) presence of at least three fused (hetero)aromatic rings and 3) electron-donor or electron donor-acceptor character which distinguishes the acenes in terms of chemical structure and unique properties from other known (hetero) acenes.

Literature:

1. Diarylmethanol Derivative into an Unknown 1,2,3,6,7,10-Hexahydroxylated Anthracene System. P. Bałczewski, M. Koprowski, A. Bodzioch, B. Marciniak, E. Różycka-Sokołowska, J. Org. Chem. 2006, 71, 2899-2902.
2. First Approach to Nitrogen‐Containing Fused Aromatic Hydrocarbons as Targets for Organoelectronics Utilizing a New Transformation of O‐Protected Diaryl Methanols. P. Bałczewski, A. Bodzioch, E. Różycka-Sokołowska B. Marciniak, P. Uznański, Chem. Eur. J. 2010,16, 2392-2400.
3. Synthesis and Optoelectronic Properties of Hexahydroxylated 10‐O‐R‐Substituted Anthracenes via a New Modification of the Friedel–Crafts Reaction Using O‐Protected ortho‐Acetal Diarylmethanols. A Bodzioch, B. Marciniak, E. Różycka-Sokołowska, J. K. Jeszka, P. Uznański, S. Kania, J. Kuliński, P. Bałczewski, Chem. Eur. J. 2012, 18, 4866-4876.
4. Milder Bradsher Conditions for Blue light Emitting Anthracenes. A. Bodzioch, B. Marciniak, E. Różycka-Sokołowska, J. K. Jeszka, P. Uznański, S. Kania, J. Kuliński, P. Bałczewski, Synfacts – Highlights in Curr. Synth. Org. Chem. 2012, 8, 619-625.
5. Use of Isomeric, Aromatic Dialdehydes in the Synthesis of Photoactive, Positional Isomers of Higher Analogs of o-Bromo(hetero)acenaldehydes. P. Bałczewski, J. Skalik, P. Uznański, D. Guziejewski, W. Ciesielski, RSC Adv. 2015, 5, 24700-24704.
6. Ultrasound-assisted synthesis of RO- and RS-substituted (hetero)acenes via oxo- and thio-Friedel-Crafts/Bradsher reactions, P. Bałczewski; E. Kowalska, J. Skalik, M. Koprowski, K. Owsianik, E. Różycka-Sokołowska, Ultrason. Sonochem. 2019. https://doi.org/10.1016/j.ultsonch.2019.104640.
7. Mono-aryl/alkylthio-substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability via Thio-Friedel Crafts/Bradsher Cyclization Reaction. P Bałczewski, E. Kowalska, E. Różycka-Sokołowska, J. Skalik, K. Owsianik, M. Koprowski, B. Marciniak, D. Guziejewski, W. Ciesielski, Chem. Eur. J. 2019, https://onlinelibrary.wiley.com/doi/10.1002/chem.201903027

2. Discovery of new organic materials with very high thermal and photochemical resistance.¹

Meaning: The highly substituted RS-(hetero)acenes obtained in the oxo-FC/B and thio-FC/B reactions have very high thermal (T_dec. = 331-354 ^oC) and exceptional photochemical stability under aerobic and anaerobic conditions, both at 254 nm and 365 nm, many times exceeding the stability of known analogues and unsubstituted anthracene (up to 1200-1900 times).

Application: optoelectronics and organo-photo-catalysis.

Literature:

1. Mono-aryl/alkylthio-substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability via Thio-Friedel Crafts/Bradsher Cyclization Reaction. P. Bałczewski, E. Kowalska, E. Różycka-Sokołowska, J. Skalik, K. Owsianik, M. Koprowski, B. Marciniak, D. Guziejewski, W. Ciesielski, Chem. Eur. J. 2019. https://onlinelibrary.wiley.com/doi/10.1002/chem.201903027

3. Discovery of the possibility of significant acceleration of homogeneous reactions proceeding through the ionic (carbocation) mechanism by using ultrasound sonication.^1,2

Meaning: Homogeneous reactions proceeding through the S_EAr carbocation mechanism, in particular oxo- and thio-F-C/B variants as well as the classic Bradsher reaction, can be, contrary to the rules of sonochemistry, significantly accelerated by means of ultrasound sonication. The unexpected acceleration compared to the reactions carried out under silent conditions exceeded 7,500 times for the oxo-variant. The mechanism involving disturbing of solvation layers and formation of the very reactive (“naked”) carbocations upon operation of the shock wave produced by the bubble collapse was considered to be the reason for this acceleration.

Literature:

1. Ultrasound-assisted synthesis of RO- and RS-substituted (hetero)acenes via oxo- and thio-Friedel-Crafts/Bradsher reactions. P. Bałczewski, E. Kowalska, J. Skalik, M. Koprowski, K. Owsianik, E. Różycka-Sokołowska, Ultrason. Sonochem. 2019. https://doi.org/10.1016/j.ultsonch.2019.104640.
2. Ultrasound-assisted Bradsher reaction in aqueous and non-aqueous media: First use of ultrasounds in electrophilic aromatic cyclisation leading to polyacenes. E. Kowalska, P. Bałczewski, Ultrason. Sonochem. 2017, 34, 743-753.

4. Discovery of the new pharmaceutical solid dyspersions of high bioavailability against hypertension and COVID-19

Patents for achievements 1-4:

1. Aromatyczne sulfotlenki i sulfony, sposób ich wytwarzania i zastosowanie (Aromatic sulfoxides and sulfones, a method of their preparation and application). P. Bałczewski, E. Kowalska, J. Skalik, M. Koprowski, K. Owsianik, E. Różycka-Sokołowska; patent RP appl., P.429272, 14.03.2019.
2. Tio-funkcjonalizowane aceny i ich zastosowanie (Thio-functionalized acenes and their application).
   P. Bałczewski, , E. Kowalska, J. Skalik, M. Koprowski, K. Owsianik, E. Różycka-Sokołowska; patent RP appl., P.4292239, 12.03.2019.
3. 10-Thiosubstituted pentahydroxyanthracene derivatives, a method of their preparation and intermediate compounds. P. Bałczewski, E. Kowalska, J. Skalik; eur. patent app., Appl. No EP-14460003.8, 06.02.2014; Patent RP udzielony No 28896539 2017, 01.02.2017.
4. Nowe skondensowane węglowodory poliaromatyczne i poliheteroaromatyczne, sposób ich wytwarzania oraz związki pośrednie (dwa patenty o tym samym tytule). P. Bałczewski, A. Bodzioch, J. Skalik, M. Koprowski; patent PL 219155, 24.07.2014; patent PL 219334, 25.08.2014.

Original publications, patents and chapters in monographs 2014 – 2020.

1. 3-Aryl-2-phosphoryl substituted 1-indanones and the method for their preparation. P. Bałczewski, D. Szczęsna, EP14150858.0, 12-01-2014.
2. Quinquevalent phosphorus acids in Organophosphorus Compounds, (review 01.01.2012 – 01.12.2012). D. W. Allen, J. C. Tebby, D. Loakes (Eds.), The Royal Society of Chemistry Publishing, P. Bałczewski, A. Bodzioch, 2014, 43, 246–347.
3. (E)-3-Aryl-3-oxoprop-1-enyl-2-phosphonate acid and its drivatives, methods for their preparation and their use, P. Bałczewski, D. Szczęsna, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska, European patent application, Sub. No 2519664, Appl. No EP-14150857.2, 12.01.2014.
4. The role of the anion in the toxicity of imidazolium ionic liquids. R. Biczak, B. Pawłowska, P. Bałczewski, P. Rychter, J. Hazard. Mater., 274, 181-190, 2014.
5. The medical use of 3-aryl substituted 1-indanones. P. Bałczewski, D. Szczęsna, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska, EP14167142.0, 06-05-2014.
6. Nowe skondensowane węglowodory poliaromatyczne i poliheteroaromatyczne, sposób ich wytwarzania, oraz związki pośrednie. P. Bałczewski, A. Bodzioch, M. Koprowski, Patent nr219334, udzielenie patentu 25.08.2014 na podstawie zgłoszenia P-385794.
7. Nowe skondensowane węglowodory poliaromatyczne i poliheteroaromatyczne, sposób ich wytwarzania, oraz związki pośrednie P. Bałczewski, A. Bodzioch, J. Skalik, M. Koprowski. Patent PL nr 219155, udzielenie patentu 24.07.2014 na podstawie zgłoszenia P-389778 z 05.12.2009 (poz.65).
8. Czwartorzędowe sole amoniowe, sposób ich wytwarzania oraz ich zastosowanie. P. Bałczewski, R. Biczak, B. Pawłowska, B. Marciniak, E. Różycka-Sokołowska, B. Dondela. Zgłoszenie patentowe P-410618, 18.12. 2014.
9. Comparison of phytotoxicity of selected phosphonium ionic liquid. R. Biczak, P. Bałczewski, B. Pawłowska, B. Bachowska, P. Rychter, Ecol. Chem. Eng. S, 21, 281-295, 2014.
10. The quaternary ammonium salts containing 2,2′-thiodiacetate anions, a method of their preparation and their use. P. Bałczewski, R. Biczak, B. Pawłowska, B. Marciniak, E. Różycka-Sokołowska, B. Dondela. Zgłoszenie patentowe, EP 15156707.0; 26.02.2015.
11. Synthesis of novel dehydroacetic acid N-aroylhydrazone-derived boron heterocycles. A. Kotali, F.Dimoulaki,E. Kotali, A. Maniadaki, P. A. Harris, E. Różycka-Sokołowska, P. Bałczewski, J. A. Joule, Tetrahedron, 71, 7245–7249, 2015.
12. Use of Isomeric, Aromatic Dialdehydes in Synthesis of Photoactive, Positional Isomers of Higher Analogs of o-Bromo(hetero)acenaldehydes, P. Balczewski, J Skalik, P. Uznanski, D. Guziejewski, W. Ciesielski, RSC Adv., 5, 24700 – 24704, 2015.
13. Quinquevalent phosphorus acids. Organophosphorus Compounds, (review 01.01.2013 – 31.12.2013). D. W. Allen, J. C. Tebby, D. Loakes (Eds.), The Royal Society of ChemistryPublishing, P. Bałczewski, J. Skalik, 2015, Vol. 44, 288-376.
14. Zastosowanie medyczne soli trifenylofosfoniowych. P. Bałczewski, J. Skalik, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska, P-413297, 28.07.2015.
15. Medical use of triphenylphosphonium salts. P. Bałczewski, J. Skalik, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska, EP15460043.1, 13.08.2015.
16. Zastosowanie soli fosfoniowych przeciw komórkom nowotworowym raka szyjki macicy HeLa lub komórkom przewlekłej białaczki szpikowej. P. Bałczewski, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska. (P-395749, 25.07.2011). Patent nr 220707. Ogłoszenie o udzieleniu patentu 31.12.2015.
17. Quinquevalent phosphorus acids in Organophosphorus Compounds, (review 01.01.2014 – 31.12.2014). D. W. Allen, J. C. Tebby, D. Loakes (Eds.), The Royal Society of Chemistry Publishing. P. Bałczewski, A. Bodzioch, 2016, Vol. 45, 196-353.
18. Total synthesis of (±)-epithuriferic acid methyl ester via Diels-Alder reaction. M. Koprowski, P. Bałczewski, K. Owsianik, E. Różycka-Sokołowska, B. Marciniak, Org. Biomol. Chem., 14, 1822-1830, 2016.
19. New hopes in cancer battle – a review of new molecules and treatment strategies. M. Turek, M. Krzyczmonik, P. Bałczewski, Med. Chem., 12 (08), 700-719, 2016.
20. 3-Arylo-2-fosforylo podstawione 1-indanony i sposób ich wytwarzania. P. Bałczewski, D. Szczęsna, (P-404112, 28.05.2013). Patent udzielony 28.11.2016 nr 223918.
21. Efficient synthesis of dibromo-bis(dibromomethyl)arenes as important precursors of synthetically useful dialdehydes. A. Bodzioch, K. Owsianik, J. Skalik, E. Kowalska, A. Stasiak, E. Różycka-Sokołowska, B. Marciniak, P. Bałczewski, Synthesis, 48, 3509-3514, 2016.
22. Nomenklatura Związków Organicznych Rekomendacje IUPAC i Nazwy Preferowane 2013. Przygotowała do publikacji Barbara Szechner, 2016. Tytuł oryginału: Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013. Prepared for publication by: Henri A. Favre, Montreal, Canada and Warren H. Powell, Columbus, OH, USA (Blue book). Rozdział P-6: Ł. Albrecht, A. Bodzioch, J. Drabowicz, T. Janecki, A. Jóźwiak, Z. Kamiński, P. Kiełbasiński, R. Karpowicz, D. Krasowska, J. Lewkowski, A. Pieczonka, M. Rachwalski, J. Skalik, P. Bałczewski, tłum. (P-62.2.6.2 do końca rozdz. P-63.5) str. 681 – 715, 2016.
23. Synthesis of Bicyclic Boron Heterocycles Containing [1,3,4,2] Oxadiazaborole and [1,3,2]Oxazaborine. A. Kotali, A. Maniadaki, E. Kotali, P. A. Harris, E. Różycka-Sokołowska, P. Bałczewski, J. A. Joule, Synthesis, 48, 4117-4125, 2016.
24. Recent studies of the synthesis, functionalization, optoelectronic properties and applications of dibenzophospholes. P. Hibner-Kulicka, J. A. Joule, J. Skalik, and P. Bałczewski, RSC Adv., 7, 9194 – 9236, 2017.
25. 10-Thiosubstituted pentahydroxyanthracene derivatives, a method of their preparation and intermediate compounds. P. Bałczewski, E. Kowalska, J. Skalik, European patent application, Appl. No EP-14460003.8, 06.02.2014. Patent udzielony No 28896539 2017, 01.02.2017.
26. Ultrasound supported Bradsher reaction in aqueous and nonaqueous media: first use of ultrasounds in electrophilic aromatic cyclisation leading to polyacenes. E. Kowalska, P. Bałczewski, Ultrason. Sonochem., 34, 743-753, 2017.
27. Quinquevalent phosphorus acids in Organophosphorus Compounds, (review (01.01.2015 – 31.12.2015). P. Bałczewski, J. Skalik, D. W. Allen, J. C. Tebby, D. Loakes (Eds.), The Royal Society of Chemistry Publishing, 2017, Vol. 46, 213-322.
28. Synthesis of polycylic (hetero)aromatic hydrocarbons via the Friedel-Crafts/Bradsher Cyclization. A. Bodzioch, E. Kowalska, J. Skalik, P. Bałczewski, Chem. Heterocycl. Compd., 53, 11-20, 2017.
29. Selective Horner-Wittig/Nazarov versus Knoevenagel/Nazarov reactions in the synthesis of biologically active 3-aryl substituted 1-indanones. D. Szczęsna, M. Koprowski, P. Bałczewski, SynLett., 28, 113-116, 2017.
30. New tetrahedral boron heterobicycles: Cyclocondensation of phenylboronic acid   with beta-keto butanoic acid N-acyl hydrazones. A. Kotali, A. Maniadaki, E. Kotali, Ph. A. Harris, E. Różycka-Sokołowska, P. Bałczewski, J. A. Joule, Tetrahedron Lett., 58, 512–515, 2017.
31. Zastosowanie medyczne beta-glukanu z owsa. P. Bałczewski, J. Kaźmierczak-Barańska, M. Cieślak, B. Nawrot, T. Zając, D. Nazarkiewicz-Zając. Zgłoszenie patentowe P-421338, 19.04.2017.
32. Zastosowanie soli jonowych zawierających kation fosfoniowy. P. Bałczewski, R. Biczak, P. Pawłowska. Nr patentu: B1 227099, 31.10.2017.
33. Synthesis of 1-indanones with a broad range of biological activity. M. Turek, D. Szczęsna, M. Koprowski, P. Bałczewski, Beilstein J. Org. Chem., 13, 451-494, 2017.
34. Spiro[4H-2,3-dihydropyran-3,3’-oxindoles] derived from 1,2,3,4-tetrahydroquinoline. B. E. Saatluo, Mehdi M. Baradarani, E. Różycka-Sokołowska, P. Bałczewski, J. A. Joule, J. Het. Chem., 55, 226-239, 2018.
35. An influence of structural changes in ammonium cations on ecotoxicity of 2,2’-thiodiacetate mono and bis-salts. R. Biczak, M. Turek, B. Pawłowska, E. Różycka-Sokołowska, B. Marciniak, M. Deska, P. Krupa, I. Jatulewicz, J. Skalik, P. Bałczewski. Ecotox. Environ. Safe., 155, 2018, 37–42.
36. Quinquevalent phosphorus acids in Organophosphorus Compounds, (review 01.01.2016 – 31.12.2016). P. Bałczewski, A. Bodzioch, D. W. Allen, J. C. Tebby, D. Loakes (Eds.). The Royal Society of Chemistry Publishing 2018, Vol. 47, 212–339.
37. Ammonium 2,2’-thiodiacetates – Selective and environmentally safe herbicides. P. Bałczewski, R. Biczak, M. Turek, B. Pawłowska, E. Różycka-Sokołowska, B. Marciniak, M. Deska, J. Skalik, Ecotox. Environ. Safe., 163, 408-416, 2018.
38. A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols. A. Czarnecka, E. Kowalska, A. Bodzioch, J. Skalik, M. Koprowski, K. Owsianik, P. Bałczewski, Beilstein J. Org. Chem., 2018, 14, 1229-1237.
39. Interactions gold/phosphorus dendrimers. Versatile ways to hybrid organic-metallic macromolecules. J. P. Majoral, M. Zabłocka, A. M. Caminade, P. Balczewski, X. Shi, S. Mignani, Coordin. Chem. Rev., 358, 2018, 80–91.
40. Ammonium haloacetates – An alternative to glyphosate? M. Turek, R. Biczak, B. Pawłowska, E. Różycka-Sokołowska, B. Marciniak, M. Deska, J. Skalik, P. Bałczewski, Chemosphere, 194, 2018, 650-656.
41. Kwas (E)-3-arylo-3-oksoprop-1-enylo-2-fosfonowy i jego pochodne – sposób ich wytwarzania oraz ich zastosowanie. P. Bałczewski, D. Szczęsna, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska. Zgłoszenie P-403432, 04.04.2013. Patent udzielony 21.06.2018.
42. The medical use of 3-aryl substituted 1-indanones. P. Bałczewski, D. Szczęsna, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska. Zgłoszenie 06.05.2014. Patent udzielony 20.06.2018, EPO 3072511.
43. Zastosowanie medyczne soli trifenylofosfoniowych. P. Bałczewski, J. Skalik, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska. Patent 413297, udzielony 29.06.2018.
44. Farmaceutyczne kokryształy antagonistów receptora angiotensyny II. Pharmaceutical co-crystals of angiotensin II receptor blockers. M. Turek, P. Bałczewski, Chem. Environ. Biotechnol., 2019, 22, 13–19.
45. Mono-aryl/alkylthio-substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability via Thio-Friedel Crafts/Bradsher Cyclization Reaction; P. Bałczewski, E. Kowalska, E. Różycka-Sokołowska, J. Skalik, K. Owsianik, M. Koprowski, B. Marciniak, D. Guziejewski, W. Ciesielski, Chem. Eur. J., 2019. https://onlinelibrary.wiley.com/doi/10.1002/chem.201903027
46. Zastosowanie medyczne 3-arylo podstawionych 1-indanonów. P. Bałczewski, D. Szczęsna, B. Nawrot, M. Cieślak, J. Kaźmierczak-Barańska, (zgłoszenie P-404485, 27-06-2013). Decyzja o udzieleniu patent 06.12.2018, pismo z 08.01.2019.
47. Dendrimer-Enabled Therapeutic Antisense Delivery Systems as Innovation in Medicine. S. Mignani, X. Shi, M. Zabłocka, J. P. Majoral,  Biocon. Chem. 2019, 30, 1938-1950
48. Design, complexing and catalytic properties of phosphorus thiazoles and benzothiazoles: A concise overview. J. P. Majoral, M. Zabłocka, M. Koprowski, A. Hameau, X. Shi, S, Mignani, A. M. Caminade,  New J. Chem 2019, 43, 16785-16795
49. Quinquevalent phosphorus acids in Organophosphorus Compounds, (01.01.2017 – 31.12.2017) P. Bałczewski, J. Skalik, D. W. Allen, J. C. Tebby, D. Loakes (Eds.), The Royal Society of Chemistry. Publishing, 2019, Vol. 48, 234-379.
50. Tio-sfunkcjonalizowane aceny i ich zastosowanie. P. Bałczewski, E. Kowalska, J. Skalik, M. Koprowski, K. Owsianik, E. Różycka-Sokołowska. Zgłoszenie patentowe, P.429239, 12.03.2019.
51. Aromatyczne sulfotlenki i sulfony, sposób ich wytwarzania i zastosowanie. P. Bałczewski, E. Kowalska, J. Skalik, M. Koprowski, K. Owsianik, E. Różycka-Sokołowska. Zgłoszenie patentowe, P.429272, 14.03.2019
52. Ultrasound-assisted synthesis of RO- and RS-substituted (hetero)acenes via oxo- and thio-Friedel-Crafts/Bradsher reactions. P.Bałczewski, E. Kowalska, J. Skalik, M. Koprowski, K.Owsianika, E. Różycka-Sokołowska, Ultrason. Sonochem. 2019, 58, 104640.
53. Ecotoxicity of ammonium chlorophenoxyacetate derivatives towards aquatic organisms: Unexpected enhanced toxicity upon oxygen by sulfur replacement. M.Turek, B. Pawłowskaa, E. Różycka-Sokołowskaa, R. Biczak, Joanna Skalik, Owsianik, B. Marciniak, P. Bałczewski, J.Haz.Mat. 2020, 382, 121086.
54. Stała ko-amorficzna dyspersja walsartanu, sposób jej syntezy oraz jej medyczne zastosowanie. Turek, M., Różycka-Sokołowska, Makowska-Janusik, M., Bałczdewski, Owsianik, K., Koprowski, M. P-433749, 29.04.2020
55. Sposób biotestowania ekotoksyczności substancji i mieszanin w fazie skondensowanej oraz jego zastosowanie w ekotoksykologii. M.Turek, P.Bałczewski, E.Różycka-Sokołowska, M.Koprowski, K.Owsianik, 22.04.2020, P.433623
56. Modification of the Microtox® Basic Solid Phase Test: a New Application for the Ecotoxicological Studies on Poorly Soluble Antihypertensive Drugs. M.Turek, P.Bałczewski, E.Różycka-Sokołowska, K.Owsianik, J.Haz.Mat. 2020, 122839.
57. Quinquevalent phosphorus acids
    in Organophosphorus Compounds, (review 01.01.2018 – 31.12.2019).
    P.Bałczewski, J.Wilk
    D. W. Allen, D. Loakes, L. J. Higham, J. C. Tebby (Eds.), The Royal Society of Chemistry Publishing, Vol. 49, 198-331 (2020).
58. The hetero-Friedel-Crafts-Bradsher cyclizations with formation of ring carbon-heteroatom (P, S) bonds, leading to organic functional materials. J. Skalik, M. Koprowski, E. Różycka-Sokołowska, P. Bałczewski, Materials, 2020, 13, 4751
59. Experimental study on the microreactor-assisted synthesis of phosphinic chlorides with varying steric hindrance, A. Jasiak, K. Owsianik, B. Gostyński, G. Mielniczak, C. Stevens, J. Drabowicz, Org. Chem. Frontiers 2020, 7, 3664-3674.
60. In search for phosphorus dendrimer-based carrier of rose bengal: tyramine linker limits fluorescent and phototoxic properties of photosensitizer, K. Sztandera, M. Marcinkowska, M. Gorzkiewicz, A. Janaszewska, R. Laurent, M. Zabłocka, S. Mignani, J.-P. Majoral, B. Klajnert-Maculewicz, Int. J. Mol. Sci. 2020, 21, article No. 4456.
61. Quinquevalent phosphorus acids.
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