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Design and Synthesis of Novel Nitrogen-Containing Heterocyclic Fluorophores and Fluorescent Nanomaterials for pH and Metal-Ion Sensing (iNFiNiTE–SENS)

Principal investigator

Category
Projekti Hrvatske zaklade za znanost
Project code
IP-2014-09-3386
Finance value
968.000
HRK
Start date
Jun 1st 2015
End date
May 31st 2019
Status
Done

Design and Synthesis of Novel Nitrogen-Containing Heterocyclic Fluorophores and Fluorescent Nanomaterials for pH and Metal-Ion Sensing (iNFiNiTE–SENS)

Design and Synthesis of Novel Nitrogen-Containing Heterocyclic Fluorophores and Fluorescent Nanomaterials for pH and Metal-Ion Sensing (iNFiNiTE–SENS)

This project brings together an interdisciplinary team of researchers with the aim to prepare novel and efficient functional materials to be used for metal-ion and pH sensing applications. Through a synergy in the synthetic, spectroscopic and computational techniques, we plan to focus our investigations on designing and characterizing a whole catalogue of compounds with desirable analytical and chemical features. Experimental work will involve traditional and "click-chemistry" strategies for the synthesis of a number of diverse benzimidazole, benzothiazole, 1,2,3-triazole, and coumarin derivatives, which will be incorporated into a range of organic, inorganic and hybrid polymeric matrices to form sensitive thin film materials or functionalized polymeric nanoparticles.

Subsequently, through the UV/Vis and fluorescence spectroscopy, these will be assessed for their abilities to form both solution- and solid-phase complexes with metal cations in order to produce usable chemosensors. The choice of the metal analytes will be prompted by either their biological significance or their presence in the environment, and will comprise cations such as Zn2+, Cu2+, Mn2+, Hg2+, Ag+, Cd2+, Fe2+/Fe3+, and Pb2+. All phases of experimental work will be supplemented with the computational support to aid in the interpretation of results. This will include calculating the conformational and tautomeric properties of investigated systems, computing the pKa profiles of organic compounds, predicting the modes and free-energies of metal binding, and, ultimately, modeling the changes in the corresponding UV-Vis absorption and emission spectra induced upon the metal complexation and solution pH modifications. In addition, molecular simulations will be advanced by considering variously substituted derivatives of the prepared organic frameworks in order to fine-tune the preferred properties, thus helping in the guided selection of future experimental directions.

Overall, the presented research is intended to pose this team for the advancements in the field of chemosensor materials with the significant promise of a wide range of industrial applications – from biomedicine to environmental sciences.

SCIENTIFIC PAPERS

E. Horak, P. Kassal, I. Murković Steinberg (2018) Benzimidazole as a structural unit in fluorescent chemical sensors: the hidden properties of a multifunctional heterocyclic scaffold, Supramolecular Chemistry, in print.

E. Horak, R. Vianello, M. Hranjec, I. Murković Steinberg (2018) Colorimetric and fluorimetric metal ion chemosensor based on benzimidazole based Schiff baseSupramolecular Chemistry, in print.

E. Horak, P. Kassal, M. Hranjec, I. Murković Steinberg (2018) Benzimidazole functionalised Schiff bases: novel pH sensitive fluorescence turn-on chromoionophores for ion-selective optodes, Sensors and Actuators B: Chemical, 258, 415-423.

T. Tandarić, R. Vianello (2018) Design of exceptionally strong organic superbases based on aromatic pnictogen-oxides: a computational DFT analysis of the oxygen basicity in the gas-phase and acetonitrile solution, Journal of Physical Chemistry A, 122, 1464–1471.

D. Dabić, L. Brkljačić, T. Tandarić, M. Žinić, R. Vianello, L. Frkanec, R. Kobetić (2018) The metal effect on self-assembling of oxalamide gelators explored by mass spectrometryJournal of The American Society for Mass Spectrometry, 29, 103-113.

M. Lokov, S. Tshepelevitsh, A. Heering, P. G. Plieger, R. Vianello, I. Leito (2017) On the basicity of conjugated nitrogen heterocycles in different media, European Journal of Organic Chemistry, 4475-4489.

E. Horak, M. Hranjec, R. Vianello, I. Murković Steinberg (2017) Reversible pH switchable aggregation-induced emission of self-assembled benzimidazole-based acrylonitrile dye in aqueous solution, Dyes and Pigments 142, 108-115.

M. Hranjec, E. Horak, D. Babić, S. Plavljanin, Z. Srdović, I. Murković Steinberg, R. Vianello, N. Perin (2017) Fluorescent benzimidazo[1,2-a]quinolines: Synthesis, spectroscopic and computational studies of protonation equilibria and metal ion sensitivity, New Journal of Chemistry 41, 358-371.

E. Horak, R. Vianello, M. Hranjec, S. Krištafor, G. Karminski Zamola, I. Murković Steinberg (2017) Benzimidazole acrylonitriles as multifunctional push-pull chromophores: spectral characterisation, protonation equilibria and nanoaggregation in aqueous solutions, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 178, 225-223.

T. Gregorić, M. Sedić, P. Grbčić, A. Tomljenović Paravić, S. Kraljević Pavelić, M. Cetina, R. Vianello, S. Raić-Malić (2017) Novel pyrimidine-2,4-dione-1,2,3-triazole and furo[2,3-d]pyrimidine-2-one-1,2,3-triazole hybrids as potential anti-cancer agents: Synthesis, computational and X-ray analysis and biological evaluation, European Journal of Medicinal Chemistry 125, 1247-1267.

Đ. Škalamera, E. Sanders, R. Vianello, A. Maršavelski, A. Pevec, I. Turel, S. I. Kirin (2016) Synthesis and characterization of ML and ML2 metal complexes with amino acid substituted bis(2-picolyl)amine ligands, Dalton Transactions 45, 2845–2858.

PARTICIPATION AT CONFERENCES

D. Babić, N. Perin, M. Hranjec, R. Vianello (2018) Protonation equlibria and optical properties of benzo[b]thienopyridil-benzimidazoles studied by spectroscopic and computational methods, Computational Chemistry Day, Zagreb, Hrvatska. (poster) 

M. Sigurnjak, P. Kassal, I. Murković Steinberg (2018) Paper-based optode for continuous monitoring of potassium concentration, EUROPT(R)ODE XIV, Naples, Italija. (poster)

K. Bobanović, E. Horak, L. Furač, I. Murković Steinberg, S. Krištafor (2018) Optical sensing properties of novel click- derived 1,2,3-triazoles and bis-triazolyl-appended benzenes, EUROPT(R)ODE XIV, Naples, Italija. (poster)

E. Horak, M. Robić, L. Furač, R. Vianello, M. Hranjec, I. Murković Steinberg (2018) Stimuli-responsive solid-state emitters based on benzimidazole moiety, EUROPT(R)ODE XIV, Naples, Italija. (poster)

N. Perin, I. Boček, B. Lončar, M. Hranjec (2018) Spektroskopska svojstva i interakcija s DNK/RNK regioizomera temeljenih na imidazo[4,5-b]piridinu, XII. Susret mladih kemijskih inženjera, Zagreb, Hrvatska. (predavanje)

A. Kapitanović, M. Cindrić, K. Starčević, M. Hranjec (2018) Amino supstituirani benzo[b]tieno[2,3-c]kinoloni kao potencijalni pH senzori i antioksidansi, XII. Susret mladih kemijskih inženjera, Zagreb, Hrvatska. (poster)

M. Hranjec, D. Babić, R. Vianello, N. Perin, E. Horak, I. Murković Steinberg (2018) Photophysical properties of fluorescent benzimidazo[1,2-a]quinolines, Central European Conference on Photochemistry CECP 2018, Bad Hofgastein, Austrija. (poster)

N. Perin, M. Hranjec, R. Vianello, D. Babić (2018) Spectroscopic and computational studies of protonation equlibria displayed by fluorescent pentacyclic benzimidazole derivatives, Central European Conference on Photochemistry CECP 2018, Bad Hofgastein, Austrija. (poster)

E. Horak, M. Hranjec, R. Vianello, N. Perin, I. Murković Steinberg (2017) Benzimidazole as a structural unit in optical chemical sensors: The hidden properties of a biologically privileged heterocyclic scaffold, 12th International Symposium on Macrocyclic and Supramolecular Chemistry: Challenges in Organic Materials & Supramolecular Chemistry, Cambridge, United Kingdom. (poster)

M. Hranjec, E. Horak, R. Vianello, N. Perin, I. Murković Steinberg (2017) Photophysical properties and immobilisation of fluorescent aminated benzimidazo[1,2-a]quinolines, 12th International Symposium on Macrocyclic and Supramolecular Chemistry: Challenges in Organic Materials & Supramolecular Chemistry, Cambridge, United Kingdom. (poster) 

K. Bobanović, E. Horak, L. Furač, M. Kralj, L. Uzelac, I. Murković Steinberg, S. Krištafor (2017) Novel 1,2,3-triazolyl-7-substituted coumarins and bis(coumarin-triazolyl)benzenes: Synthesis, photophisical properties and cytostatic evaluation, 10th Joint Meeting on Medicinal Chemistry, Dubrovnik, Hrvatska. (poster) 

E. Horak, M. Hranjec, N. Perin, R. Vianello, L. Furač, I. Murković Steinberg (2017) Aggregation-induced emission (AIE) of self-assembled benzimidazole based acrylonitrile dye, XV. hrvatski skup kemičara i kemijskih inženjera, Poreč, Hrvatska. (predavanje)

E. Horak, M. Hranjec, N. Perin, R. Vianello, S. Krištafor, I. Murković Steinberg (2017) pH and metal sensing properties of benzimidazole based Schiff bases, XV. hrvatski skup kemičara i kemijskih inženjera, Poreč, Hrvatska. (poster)

I. Sović, I. Boček, P. Roškarić, K. Starčević, R. Vianello, M. Hranjec (2017) Antioxidative activity and metal and pH sensing properties of heteroaromatic benzamides, XV. hrvatski skup kemičara i kemijskih inženjera, Poreč, Hrvatska. (poster)

E. Horak, Š. Kamenić, N. Perin, M. Hranjec, I. Murković Steinberg (2016) Optical properties of novel iminocoumarine derivatives in solutions and polymer matrices, XIII Conference on Optical Chemical Sensors and Biosensors - EUROPT(R)ODE, Graz, Austria. (poster) 

E. Horak, K. Bobanović, M. Sigurnjak, M. Marinović, N. Pantalon Juraj, I. Murković Steinberg, S. Krištafor (2016) Design, synthesis and immobilization of novel click-derived triazoles for the application in (bio)chemical sensor materials, XIII Conference on Optical Chemical Sensors and Biosensors - EUROPT(R)ODE, Graz, Austria. (poster) 

N. Perin, K. Bobanović, M. Hranjec (2016) Synthesis of novel substituted cyclic benzimidazole derivatives, XI. Susret mladih kemijskih inženjera, Zagreb, Hrvatska. (poster) 

PhD THESES

Ema Horak (2017) Kemijski optički senzori temeljeni na derivatima benzimidazola, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Ivana Steinberg)

DIPLOMA THESES

Petra Roškarić (2017) Sinteza, spektroskopska karakterizacija i antioksidativna aktivnost novih metoki- i hidroksi-supstituiranih heteroaromatskih derivata, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Marijana Hranjec, neposredni voditelji: Nataša Perin, Irena Sović)

Ida Boček (2017) Sinteza i spektroskopska karakterizacija novih amino-supstituiranih tetracikličkih derivata imidazo[4,5-b]piridina, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Marijana Hranjec, neposredni voditelj: Nataša Perin)

Marko Robić (2017) Emisija izazvana agregacijom (EIA) u razvoju novih fluorescentnih proba i senzora, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Lidija Furač, neposredni voditelj: Ema Horak)

Vedran Vučić (2017) Primjena fluorescentnih derivata benzimidazola u funkcionalnim materijalima, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Ivana Steinberg, neposredni voditelj: Ema Horak)

Leo Dorogi (2017) Spektroskopska ispitivanja novih fluorescentnih probi temeljenih na benzimidazolu za određivanje pH i metalnih iona, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Svjetlana Krištafor, neposredni voditelj: Kristina Bobanović)

Dejan Bogojević (2017) Sinteza i optička karakterizacija novih heteroaromatskih kromofora, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Lidija Furač, neposredni voditelj: Ema Horak)

Mario Vitek (2016) Novi donorsko-akceptorski konjugati s triazolnom poveznicom kao potencijalne pH probe i kemijski senzori za metalne ione, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Svjetlana Krištafor, neposredni voditelj: Kristina Bobanović)

FINAL THESES

Angela Kapitanović (2017) Amino- i nitro-supstituirani benzo[b]tieno[2,3-c]kinoloni kao potencijalni antioksidansi, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Marijana Hranjec, neposredni voditelj: Maja Cindrić)

Lucija Višić (2017) Primjena click-kemije u sol-gel materijalima, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Ivana Steinberg, neposredni voditelj: Ema Horak)

Igor Lukanović (2017) Fotofizička svojstva novih benzimidazol-1,2,3-triazol bis-heterocikla, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Lidija Furač, neposredni voditelj: Kristina Bobanović)

Katarina Majnarić (2017) Fluorescencijski kemijski senzori temeljeni na kumarinu, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Lidija Furač, neposredni voditelj: Kristina Bobanović)

Lucija Rebrović (2017) Heterociklički donorsko-akceptorski sustavi: odnos struktura-fotofizička svojstva, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Svjetlana Krištafor, neposredni voditelj: Kristina Bobanović)  

Emina Džanić (2017) Uloga 1,2,3-triazola kao heteroaromatske gradivne jedinice u koordiniranju na metalne ione, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Svjetlana Krištafor, neposredni voditelj: Kristina Bobanović)

Adriana Katavić (2016) Spektroskopska karakterizacija benzo[b]tieno-2-karboksamida u prisustvu metalnih kationa korištenjem UV/Vis i fluorimetrijske spektroskopije, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Marijana Hranjec)

RECTOR'S AWARDS

Ida Boček (2017) Utjecaj položaja dušikovog atoma na spektroskopska svojstva i interakciju s DNK/RNK regioizomera temeljenih na imidazo[4,5-b]piridinu, Fakultet kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu. (mentor: Marijana Hranjec, neposredni voditelj: Nataša Perin)

Other associates

  1. Dr. Darko Babić - Ruđer Bošković Institute, Zagreb
  2. Dr. Ines Despotović - Ruđer Bošković Institute, Zagreb
  3. Dr. Nena Radić - Ruđer Bošković Institute, Zagreb
  4. Dr. Ivana Steinberg - Faculty of Chemical Engineering and Technology, University of Zagreb
  5. Dr. Marijana Hranjec - Faculty of Chemical Engineering and Technology, University of Zagreb
  6. Dr. Svjetlana Krištafor - Faculty of Chemical Engineering and Technology, University of Zagreb
  7. Dr. Lidija Furač - Faculty of Chemical Engineering and Technology, University of Zagreb
  8. Dr. Irena Sović - Faculty of Chemical Engineering and Technology, University of Zagreb
  9. Dr. Maja Cindrić - Faculty of Chemical Engineering and Technology, University of Zagreb
  10. Dr. Nataša Perin - Faculty of Chemical Engineering and Technology, University of Zagreb
  11. Dr. Ema Horak - Faculty of Chemical Engineering and Technology, University of Zagreb

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