Excellence Initiative - Research University
ul. Gagarina 7, 87-100 Toruń
tel.: +48 56 611-43-02
fax: +48 56 611-45-26
e-mail: wydzial@chem.umk.pl

Department of Organic Chemistry


Scientific interests of the Department involve several research fields. The group of prof. Jacek Ścianowski deals with the synthesis of new organocatalyst and bioactive agents based on chalcogens, especially selenium. The synthetized organoselenium compounds, selenides, diselenides,  selenols, benzisoselenazolones and selenonium salts, in the form of chiral terpene or aminoacid derivatives are tested as reagents and catalyst in various reaction protocols. The significant biological activity of selected compounds is associated with their antioxidant, anticancer, antibacterial and antiviral properties, and is evaluated in cooperation with several research groups in Poland, Italy, Brasil, and USA.

The main interests of Borys Ośmiałowski, prof. NCU group is the synthesis and optimization of fluorescent dyes in the light of their photophysical properties. The aim is to develop a class of compounds useful in, inter alia, two-photon bioimaging. That is realized by the palette of methods of modification of their structure related to a) benzannulation, b) extension of the conjugation path, c) substituent effect, d) exchange of single atoms in the structure of fluorophores, e) changing the position of the heteroatom in isomeric compounds, f) change of the geometry in donor-acceptor molecules, but also by g) modification of properties in the supramolecular regime, h) tuning the topology of molecules for crystal engineering.

The team of Zbigniew Rafiński, prof. NCU is involved in the search for strategies for reaction methodology development to stand on contemporary problems in reaction discovery, and targeted synthesis. Their research interests focus on asymmetric organocatalysis with the use of chiral low-molecular organic molecules, the role of which is played by N-heterocyclic carbenes capable of catalytically acting in various stereo-differentiating reactions. Moreover, their activities include the design of new organocatalysts, and also the development of new synthetic strategies enabling the synthesis of many structurally diverse and synthetically useful chiral compounds.

The studies conducted in the group of Marek Krzemiński, prof. NCU are related to the synthesis of chiral monoterpene derivatives. The ingredients of polish turpentine from Pinus Silvestris pine, α-pinene, β-pinene, and 3-carene are compounds from which they obtain β-amino alcohols, precursors of several developed catalysts. They apply obtained derivatives in catalytic enantioselective reduction and addition reactions.

Research topics of Agnieszka Tafelska-Kaczmarek, PhD include the synthesis of various new heterocyclic compounds, mainly benzofuran and benzothiophene derivatives; asymmetric synthesis using chiral reduction catalysts; synthesis of compounds with potential biological properties.

The group of Mariusz Bosiak, PhD designs, synthesizes and studies organic fluorophores that exhibit prompt emission of light. Based on the DFT method, the group is developing new organic fluorescence emitters adjusted to TADF emitters for new electroluminescent devices based on hyperfluorescence. Synthesis of designed fluorophores is performed with the use of organic catalysts developed in the group. The target compounds show fluorescence with PLQY up to 100%.


Head – prof. Jacek Ścianowski, jsch@umk.pl  +48-56-611-4532
Marek Krzemiński, prof. NCU, mkrzem@umk.pl , +48-56-611-4358
Borys Ośmiałowski, prof. NCU, borys.osmialowski@umk.pl , +48-56-611-4514
Zbigniew Rafiński, prof. NCU, payudo@chem.umk.pl , +48-56-611-4321
Mariusz Bosiak, PhD, bosiu@umk.pl , +48-56-611-4531
Anna Kmieciak, PhD, akmieciak@umk.pl , +48 56 611-4322
Magdalena Obieziurska-Fabisiak, PhD, magdao@umk.pl
Agata Pacuła-Miszewska, PhD, pacula@umk.pl
Agnieszka Tafelska-Kaczmarek, PhD, tafel@umk.pl , +48-56-611-4544
Andrzej Wolan, PhD, wolan@umk.pl , +48-56-611-4323
Marta Plaskacz-Dziuba, MSc, martapl@umk.pl , +48-56-611-4329
Jakub Szumera, MSc, szumera@umk.pl+48-56-611-4329

PhD Students
Joanna Andrusiak, Msc
Izabela Barańska, MSc
Krzysztof Dzieszkowski, MSc
Karolina Jeżak, Msc
Anna Laskowska, MSc
Karina Mroczyńska, MSc
Julianna Mruk, MSc
Patrycja Olejkowska, Msc
Natalia Piórkowska, Msc
Marcin Rakowiecki, Msc
Alejadro Iglesias Reguant, MSc
Patryk Rybczyński, MSc
Judyta Zielak, MSc


NCN Grants:

prof. Jacek Ścianowski, „Changes in iron metabolism induced by anticancer compounds in in vitro and in vivo” financed by National Science Centre (Opus program grant realized as part of a consortium with prof. Jędrzej Antosiewicz GUMed) 27.04.2016-26.04.2021

Borys Ośmiałowski, prof. UMK, “Boron-based Fluorophores – Functionalisation, Properties and Their Tests for Versatile Usage” financed by National Science Centre (Harmonia program) 21.05.2018-20.05.2022

Borys Ośmiałowski, prof. UMK “Development of new class of fluorophores based on boron centre with tailored photophysical properties” financed by National Science Centre (Opus program) 10.06.2020-9.06.2024

Zbigniew Rafiński, prof. UMK, “Synthesis and application of new chiral triazolium salts derived from terpenes as N-heterocyclic carbene precocatalysts (NHCs) for asymmetric synthesis” financed by National Science Centre (Sonata program) 29.08.2012-29.08.2015

Zbigniew Rafiński, prof. UMK, Organocatalytic synthetic strategies with the use of N-heterocyclic carbenes – new directions and applications, financed by National Science Centre (Sonata Bis program) 06.04.2017-06.04.2022

Mariusz Bosiak, PhD, „Opracowanie dogodnej metody katalizowanego palladem aminowania halogenków i pseudohalogenków heterocyklicznych drugorzędowymi aminami aromatycznymi wobec znanych i autorskich ligandów fosfinowych – badania wstępne.” financed by National Science Centre (Miniatura program)

Agata Pacuła-Miszewska, PhD, „Seleniany rozpuszczalne w wodzie – rozwiązanie problemu niskiej biodostępności związków selenoorganicznych – badania wstępne” financed by National Science Centre (Miniatura program)


J. Mruk, A. Pacuła-Miszewska, L. Pazderski, J. Drogosz-Stachowicz, A. Janecka, J. Ścianowski Intramolecular C-N bond formation via thermal arene C-H bond activation supported by Au(III) complexes Materials 2021, 14, 1676.

J. Andrusiak, K. Mylkie, M. Wysocka, J. Ścianowski, A. Wolan, M. Budny Synthesis of xanthohumol and xanthohumol-d3 from naringenin. RSC Advances 2021, 11, 28934-28939.

K. Dzieszkowski, M. Słotwiński, K. Rafińska, T. M. Muzioł, Z. Rafiński, NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenones via α,β-unsaturated acyl azoliums, Chem. Commun. 2021, 57, 9999-10002; highlighted with a Inside Front Cover

B. Ośmiałowski, E.F. Petrusevich, K. C. Nawrot, B. K. Paszkiewicz, M. Nyk, J. Zielak, B. Jȩdrzejewska, J. M. Luis, D. Jacquemin, R. Zaleśny, Tailoring the Nonlinear Absorption of Fluorescent Dyes by Substitution at a Boron Center, J. Mater. Chem. C, 2021, 9, 6225-6233.

M. Obieziurska, A. J. Pacuła, A. Laskowska, A. Długosz-Pokorska, A. Janecka, J. Ścianowski, Seleninic acid potassium salts as water-soluble biocatalysts with enhanced bioavailability Materials 2020, 13, 661.

K. Dzieszkowski, Z. Rafiński, N-Heterocyclic Carbene-Catalyzed Enantioselective Intramolecular Annulations to Construct Benzo-Fused Pyranones with Quaternary Stereocenter, Adv. Synth. Catal. 2020, 362, 3830-3835.

B. Ośmiałowski, E. F. Petrusevich, M. A. Antoniak, I. Grela, M. A. Bin Jassar, M. Nyk, J. M. Luis, B. Jędrzejewska, R. Zaleśny, D. Jacquemin, Controlling Two-Photon Action Cross Section by Changing a Single Heteroatom Position in Fluorescent Dyes, J. Phys. Chem. Lett. 2020, 11, 5920-5925.

A. Tafelska-Kaczmarek, R. Kołodziejska, M. Kwit, B. Stasiak, M. Wypij, P. Golińska, Synthesis, Absolute Configuration, Antibacterial, and Antifungal Activities of Novel Benzofuryl β-Amino Alcohols Materials 2020, 13, 4080.

R. Kołodziejska, R. Studzińska, A. Tafelska-Kaczmarek, H. Pawluk, B. Stasiak, M. Kwit, A. Woźniak, Effect of chemical structure of benzofuran derivatives and reaction conditions on enantioselective properties of Aureobasidium pullulans microorganism contained in Boni Protect antifungal agent Chirality 2020, 32, 407-415.

A. Kmieciak, M. P. Krzemiński, Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene, Beilstein J. Org. Chem. 2019, 15, 2493–2499.

A. Kmieciak, M. P. Krzemiński, Chiral terpene auxiliaries IV: new monoterpene PHOX ligands and their application in the catalytic asymmetric transfer hydrogenation of ketones, Tetrahedron: Asymm. 2017, 28, 467-472.

M. J. Bosiak, P. Trzaska, D. Kędziera, J. Adams, Synthesis and photoluminescence properties of star-shaped 2,3,6,7-tetrasubstituted benzo[1,2-b:4,5-b′]difurans Dyes & Pigments, 2016, 129, 199-208.

M. J. Bosiak, A convenient synthesis of 2-arylbenzo[b]furans from aryl halides and 2-halophenols by catalytic one-pot cascade method, ACS Catalysis, 2016, 6, 2429-2434.