Project title: Synthesis and photochemistry/photophysics studies of the intelligent luminescent molecular sensors for selective detection in biochemistry and chemistry

Project number: POIR.04.04.00-00-1E42/16-00

Principal investigator: PhD Associate Professor Joanna Ortyl

Obtained funds: 800 000,00 PLN

Funding source:

Foundation for Polish Science 

Project duration:

Start day: 10.2016

End day: 09.2019

Short disctoption of the project:

The project's main objective was the design, synthesis, characterization, and investigations of compounds that exhibit luminescence or fluorescence strongly dependent on changes in their environment. These compounds were applied in biological and chemical studies, pharmaceutical and polymer industries, and environmental protection. The new high-performance luminescent molecular sensors were investigated for quantitative spectrophotometric and spectrofluorometric studies. The developed novel systems were examined for their suitability, efficiency, and effectiveness in real-time monitoring of various processes using spectrometric methods. The prepared systems were characterized in terms of their lifetime and quantum yield of fluorescence, photostability, Stokes' shift, and the value of the dipole moment in the excited state. Probes with the highest values of features mentioned above will be particularly desirable because of their strong dependence on the changes of pH, polarity, ionic strength, viscosity, formation of hydrogen bonds, and presence of quenchers. These compounds were applied in biological and chemical studies, the pharmaceutical and polymer industry, and environmental protection.

The REINTEGRATION Programme is part of the Grant Project of the Foundation for Polish Science European Funds within the Smart Growth Operational Programme 2014–2020 Priority Axis IV: Increasing the scientific research potential Measure 4.4: Increasing the human potential in the R&D sector.

The Foundation for Polish Science has been in operation since 1991. It is a non-governmental, non-political, non-profit institution that pursues the mission of supporting science. It is the largest source of science funding in Poland outside of the state budget.

Project outcomes:

Patent application 

1. Zgłoszenie patentowe P.426056

Data: 25.06.2018

Tytuł zgłoszenia patentowego: New quinoline-2-one derivatives, their production method, new photoinitiating systems for cationic, radical, thiol-en and hybrid cationic polymerization processes and the use of new quinolin-2-one derivatives.

Autorzy: Joanna Ortyl, Monika Topa, Filip Petko, Kamil Machowski, Mariusz Galek

2. Zgłoszenie patentowe P.426019

Data: 22.06.2018

Autorzy: Maciej Pilch, Joanna Ortyl, Mariusz Galek, Roman Popielarz

Tytuł zgłoszenia patentowego: Sposób mapowania rozkładu ciśnienia na powierzchniach materiałów powłokowych przy użyciu sensorów luminescencyjnych i układ do mapowania rozkładu ciśnienia na powierzchniach materiałów powłokowych przy użyciu sensorów luminescencyjnych

3. Zgłoszenie patentowe P.429090

Data: 27-02-2019

Autorzy: J. Ortyl. A.Chachaj-Brekiesz, P. Fiedor, P. Szymaszek, K. Dzięciołowska, W. Kasprzyk, T. Świergosz, Mariusz Galek

Tytuł zgłoszenia patentowego: Nowe pochodne 4,6-difenylo-pirydyno-3-karbonitrylu, sposoby wytwarzania pochodnych 4,6-difenylo-pirydyno-3-karbonitrylu, nowe systemy fotoinicjujące do procesów fotoinicjowanej polimeryzacji kationowej, rodnikowej, tiol-en i hybrydowej oraz zastosowania pochodnych 4,6-difenylo-pirydyno-3-karbonitrylu

4. Zgłoszenie patentowe P.431041

Data: 04.09.2019

Autorzy: Joanna Ortyl, Anna Chachaj-Brekiesz, Monika Topa, Karolina Dzięciołowska, Magdalena Jankowska, Patryk Szymaszek, Filip Petko, Wiktor Kasprzyk, Tomasz Świergosz, Mariusz Galek

Tytuł zgłoszenia patentowego: Nowe pochodne 3-(2-pirydylo)chromen-2-onu, sposób ich wytwarzania i zastosowania, nowe związki pośrednie do wytwarzania nowych pochodnych 3-(2-pirydylo)chromen-2-onu, sposób wytwarzania związków pośrednich oraz zastosowanie związków pośrednich

5. Zgłoszenie patentowe P.431042

Data: 04.09.2019

Autorzy: oanna Ortyl, Anna Chachaj-Brekiesz, Monika Topa, Karolina Dzięciołowska, Magdalena Jankowska, Patryk Szymaszek, Filip Petko, Wiktor Kasprzyk, Tomasz Świergosz, Mariusz Galek

Tytuł zgłoszenia patentowego: Nowe pochodne 3-(2-pirydylo)chromen-2-onu, sposób ich wytwarzania i zastosowania oraz zastosowanie związków pośrednich.

Publications

• D. Nowak, J. Ortyl, I. Kamińska-Borek, K. Kukuła, M. Topa, R. Popielarz, , Photopolymerization of hybrid monomers, part I: Comparison of the performance of selected photoinitiators in cationic and free-radical polymerization of hybrid monomers, Polymer Testing, 2017, 64, 313-320.
• M.Topa, J. Ortyl, A. Chachaj-Brekiesz, I. Kamińska-Borek, M. Pilch, R. Popielarz, Applicability of samarium(III) complexes for the role of luminescent molecular sensors for monitoring progress of photopolymerization processes and control of the thickness of polymer coatings, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, 15;199:430-440.
• D. Nowak, J. Ortyl, I. Kamińska-Borek, K. Kukuła, M. Topa, R. Popielarz, Photopolymerization of hybrid monomers, part II: Determination of relative quantum efficiency of select, Polymer Testing, 2018, 67, 144-150.
• M. Topa, F. Petko, M. Galek, K. Machowski, M. Pilch, P. Szymaszek J. Ortyl “Applicability of 1,6-Diphenylquinolin-2-one Derivatives as Fluorescent Sensors for Monitoring the Progress of Photopolymerisation Processes and as Photosensitisers for Bimolecular Photoinitiating Systems”, Polymers, 2019, 11(11), 1756.
• J. Ortyl, I. Kamińska-Borek, M. Topa, R. Popielarz, 2019, Mechanism of interaction of aminocoumarins with reaction medium during cationic photopolymerization of monomers, European Polymer Journal, 2019, 116, 45–55.
• J. Ortyl, P. Fiedor, A. Chachaj-Brekiesz, M. Pilch, E. Hola, M. Galek, The applicability of 2-amino-4,6-diphenyl- pyridine-3-carbonitrile sensors for monitoring different types of photopolymerization processes and acceleration of cationic and free-radical photopolymerization under near UV light, Sensors 2019,19(7), 1668.
• MaciejPilch, Joanna Ortyl, Anna Chachaj-Brekiesz, Mariusz Galek, Roman Popielarz, Europium-based luminescent sensors for mapping pressure distribution on surfaces, Sensors and Actuators B: Chemical, 2020, 305, 127409.

Awards

• Monika Topa, Maciej Pilch, Karolina Dzięciołowska - First place in the 12th national competition for innovative solutions developed by young inventors „YOUNG INVENTOR 2017”, under the honorary patronage of the Vice-President of the Council of Ministers, Minister of Science and Higher Education Jaroslaw Gowin for the solution „New high-performance luminescent lanthanide complexes and their application to the role of organic-inorganic luminescent molecular chemosensors in on-line polymer coating materials and in the initiation of photopolymerization processes”. Type of reward: team (Monika Topa, Katarzyna Kukuła, Maciej Pilch, Karolina Dzięciołowska)
• MONIKA TOPA - Winner of the first step of the competition for the ABB award for the Engineer's Thesis in the academic year 2017/2018. Type of award: individual; Range of the competition: nationwide; Sponsor of the award: ABB
• MONIKA TOPA - Winner of the competition for the best Bachelor's / Engineer's Thesis "Złoty Medal Chemii 2017" made in the academic year 2016/2017 and distinction in this competition for the Engineer's Thesis "Badania przydatności kompleksów metali ziem rzadkich do roli luminescencyjnych sensorów molekularnych ". Type of award: individual; Range of the competition: nationwide; Sponsor of the award: Instytut Chemii Fizycznej Polskiej Akademii Nauk in Warsaw
• MONIKA TOPA - The special distinction of the DuPont company in the national competition for the best Bachelor's / Engineer's Thesis "Złoty Medal Chemii 2017"made in the academic year 2016/2017 for the Engineer's Thesis "Badania przydatności kompleksów metali ziem rzadkich do roli luminescencyjnych sensorów molekularnych " Type of award: individual; Range of the competition: nationwide; Sponsor of the award: DuPont company
• MONIKA TOPA - First Degree Prize awarded by the Foundation for the Promotion of Young Talents in 2018 for the overall delays during the first and second cycle studies at the Faculty of Chemical Engineering and Technology of the Cracow University of Technology, authorship of articles published in the journal from the A list - Ministry of Science and Higher Education. Type of award: individual. Range of the competition: national. Sponsor of the award: Founder of the Foundation for the Support of Young Talents of Professor Janusz Magiera at the Cracow University of Technology
• MONIKA TOPA - 1st degree prize in the category of Technologies in the Competition for the best Master's theses in the field of entrepreneurship, innovation and regional development for the master's thesis entitled "Spectroscopic studies of new 1,6-diphenyl-quinolin-2-one derivatives and evaluation of their suitability for acceleration and monitoring of photopolymerization processes", (18/12/2018). Type of award: individual. Range of the competition: national. Sponsor of the award: Małopolska Agencja Rozwoju Regionalnego SA
• MONIKA TOPA - 1st place in the competition Jerzy Haber for his master's thesis on physicochemistry of surfaces and catalysis titled "Spectroscopic studies of the new derivatives 1,6-diphenyl-quinolin-2-one and evaluation of their suitability for acceleration and monitoring of photopolymerization processes" Type of award: individual. Range of the competition: national. Sponsor of the award: Instytut Katalizy i Fizykochemii Wladys im. Jerzy Haber Polish Academy of Sciences
• MACIEJ PILCH - Winning the third place (bronze medal) in a nationwide competition Gold Medal of Chemistry 2018 (Institute of Physical Chemistry) for work „Study of the effect of pressure on the molecular emission characteristics of luminescent sensors in polymeric coating materials”; Type of reward: individual (Maciej Pilch)
• MACIEJ PILCH - Acquiring the prize of the Foundation for Supporting Young Talents of Professor Janusz Magiera
• MACIEJ PILCH - 1st place in the competition for the best lecture during The University Students' Scientific Session of the Cracow University of Technology . Conference name: The University Students' Scientific Session of the Cracow University of Technology Scope of the conference: local conference. Organizer of the conference: Cracow University of Technology, Faculty of Chemical Engineering and Technology. Title of the presentation: Applications of luminescent sensors for mapping pressure distribution on surfaces
• MONIKA TOPA - Scholarship of the Minister of Science and Higher Education for outstanding achievements in the academic year 2017/2018.
• MONIKA TOPA - Science Scholarship for special scientific achievements awarded by the Małopolska Scholarship Foundation SAPERE AUSO in the academic year 2017/2018