Photocatalytic application of water-soluble metalloporphyrins: an experimental and theoretical study

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Details of project

Identifier

107310

Type

Principal investigator

Horváth, Ottó

Title in Hungarian

Vízoldható metalloporfirinek fotokatalitikus alkalmazása: kísérleti és elméleti vizsgálatok

Title in English

Photocatalytic application of water-soluble metalloporphyrins: an experimental and theoretical study

Keywords in Hungarian

vízoldható metalloporfirinek, fotokatalízis, fotokémia, fotofizika

Keywords in English

water-soluble metalloporphyrins, photocatalysis, photochemistry, photopysics

Discipline

Physical Chemistry and Theoretical Chemistry (Council of Physical Sciences)	100 %
Ortelius classification: Photochemistry

Panel

Chemistry 1

Department or equivalent

TTK Környezeti és Szervetlen Fotókémia (University of Pannonia)

Participants

Fodor, Lajos
Kovács, Margit
Lendvay, György
Valicsek, Zsolt
Zsilák, Zoltán

Starting date

2012-09-01

Closing date

2016-08-31

Funding (in million HUF)

35.998

FTE (full time equivalent)

5.92

state

closed project

Summary in Hungarian

A kutatás összefoglalója, célkitűzései szakemberek számára
Itt írja le a kutatás fő célkitűzéseit a témában jártas szakember számára.
Metalloporphyrins are key compounds in nature, but their advantageous coordination, redox and photoinduced properties can also be exploited in artificial systems, e.g., in photocatalytic procedures. According to our preliminary results, water-soluble sitting-atop (SAT) metalloporphyrins containing large-diameter metal ions located out of the plane of the porphyrin ligand exhibit unique photochemistry: they undergo efficient ligand-to-metal charge-transfer processes following absorption of visible light. This photoactivity allows their utilization as catalysts in cyclic processes for synthesis of special chemicals or compounds storing solar energy. The main goal of the proposed project is the elucidation of the mechanism of the photoredox reactions of water-soluble SAT metalloporphyrins, and, on the basis of these fundamental results, establishment of catalytic systems utilizing these and also in-plane complexes in preparative or photochemical water-splitting procedures for future renewable energy technology and green chemistry.

Mi a kutatás alapkérdése?
Ebben a részben írja le röviden, hogy mi a kutatás segítségével megválaszolni kívánt probléma, mi a kutatás kiinduló hipotézise, milyen kérdéseket válaszolnak meg a kísérletek.
In the case of water-soluble sitting-atop (SAT) metalloporphyrins the photoinduced charge transfer from ligand to metal ion makes the charge separation more efficient, which allows their utilization as catalysts in cyclic processes for synthesis of chemicals suitable for conservation of light energy. In such a cycle, an appropriate electron donor and acceptor (reductant – oxidant) pair reacting with the primary products of the photoinduced LMCT process can regenerate the starting photocatalyst and lead to end-products for energy storage or as special chemicals. In an other concept of photoredox catalysis based on metalloporphyrin the starting metalloporphyrin is a normal (in-plane) complex, but it becomes of SAT type when the same metal centre is photoreduced to a lower oxidation state in the presence of suitable electron donor. This SAT complex of high reactivity can be oxidized by an appropriate electron acceptor in a thermal or light-driven way, regenerating the starting chromophore and giving an end-product or a reactive reductant, which can produce an energy storing final product. In order to achieve these goals, the following main questions should be addressed:
What is the mechanism of the photoredox reactions involving water-soluble SAT complexes?
How does the size and the electronic configuration of the metal centre and the structure of the porphyrin ligand influence the photochemistry of these complexes?
What types of electron donors and acceptors can be applied for realization of photocatalytic systems generating end-products to store energy?

Mi a kutatás jelentősége?
Röviden írja le, milyen új perspektívát nyitnak az alapkutatásban az elért eredmények, milyen társadalmi hasznosíthatóságnak teremtik meg a tudományos alapját. Mutassa be, hogy a megpályázott kutatási területen lévő hazai és a nemzetközi versenytársaihoz képest melyek az egyediségei és erősségei a pályázatának!
Solar radiation is the most significant and accessible renewable energy source available on Earth. Besides, photochemical reactions offer the possibility to design procedures of very mild conditions with higher selectivity and efficiency for production of various compounds the synthesis of which via thermal reactions needs much more extreme circumstances, and, thus, higher cost. Further enhances the favourable features of photochemical technologies if one is able to apply water as solvent, making the technology environmentally benign. Since light is a clean energy source, aqueous photocatalytic systems driven by solar light can be good representatives of green chemistry.
Via utilization of water-soluble out-of-plane (SAT) metalloporphyrins, photocatalytic systems exploiting solar energy in the visible range can be realized. In-plane metalloporphyrins which can be photochemically reduced to also photoactive SAT complexes can also be applied in such catalytic systems, increasing the feasibility of this concept.

A kutatás összefoglalója, célkitűzései laikusok számára
Ebben a fejezetben írja le a kutatás fő célkitűzéseit alapműveltséggel rendelkező laikusok számára. Ez az összefoglaló a döntéshozók, a média, illetve az érdeklődők tájékoztatása szempontjából különösen fontos az NKFI Hivatal számára.
Metalloporphyrins such as chlorophylls play very important roles in nature, but their advantageous photochemical properties can also be exploited in artificial photocatalytic systems utilizing visible light. Water-soluble sitting-atop (SAT) metalloporphyrins containing large-diameter metal ions located out of the plane of the porphyrin ligand exhibit unique photochemistry, offering the possibilities of their application as catalysts in cyclic processes for synthesis of special chemicals or compounds storing solar energy. The main goal of the proposed project is the elucidation of the mechanism of these reactions, and, on the basis of this knowledge, realization of catalytic systems utilizing both out-of-plane and also in-plane porphyrin complexes for preparative or photochemical water-splitting procedures. These systems may be key units of environmentally benign future technologies driven by solar light as renewable energy.

Summary

Summary of the research and its aims for experts
Describe the major aims of the research for experts.
Metalloporphyrins are key compounds in nature, but their advantageous coordination, redox and photoinduced properties can also be exploited in artificial systems, e.g., in photocatalytic procedures. According to our preliminary results, water-soluble sitting-atop (SAT) metalloporphyrins containing large-diameter metal ions located out of the plane of the porphyrin ligand exhibit unique photochemistry: they undergo efficient ligand-to-metal charge-transfer processes following absorption of visible light. This photoactivity allows their utilization as catalysts in cyclic processes for synthesis of special chemicals or compounds storing solar energy. The main goal of the proposed project is the elucidation of the mechanism of the photoredox reactions of water-soluble SAT metalloporphyrins, and, on the basis of these fundamental results, establishment of catalytic systems utilizing these and also in-plane complexes in preparative or photochemical water-splitting procedures for future renewable energy technology and green chemistry.

What is the major research question?
Describe here briefly the problem to be solved by the research, the starting hypothesis, and the questions addressed by the experiments.
In the case of water-soluble sitting-atop (SAT) metalloporphyrins the photoinduced charge transfer from ligand to metal ion makes the charge separation more efficient, which allows their utilization as catalysts in cyclic processes for synthesis of chemicals suitable for conservation of light energy. In such a cycle, an appropriate electron donor and acceptor (reductant – oxidant) pair reacting with the primary products of the photoinduced LMCT process can regenerate the starting photocatalyst and lead to end-products for energy storage or as special chemicals. In an other concept of photoredox catalysis based on metalloporphyrin the starting metalloporphyrin is a normal (in-plane) complex, but it becomes of SAT type when the same metal centre is photoreduced to a lower oxidation state in the presence of suitable electron donor. This SAT complex of high reactivity can be oxidized by an appropriate electron acceptor in a thermal or light-driven way, regenerating the starting chromophore and giving an end-product or a reactive reductant, which can produce an energy storing final product. In order to achieve these goals, the following main questions should be addressed:
What is the mechanism of the photoredox reactions involving water-soluble SAT complexes?
How does the size and the electronic configuration of the metal centre and the structure of the porphyrin ligand influence the photochemistry of these complexes?
What types of electron donors and acceptors can be applied for realization of photocatalytic systems generating end-products to store energy?

What is the significance of the research?
Describe the new perspectives opened by the results achieved, including the scientific basics of potential societal applications. Please describe the unique strengths of your proposal in comparison to your domestic and international competitors in the given field.
Solar radiation is the most significant and accessible renewable energy source available on Earth. Besides, photochemical reactions offer the possibility to design procedures of very mild conditions with higher selectivity and efficiency for production of various compounds the synthesis of which via thermal reactions needs much more extreme circumstances, and, thus, higher cost. Further enhances the favourable features of photochemical technologies if one is able to apply water as solvent, making the technology environmentally benign. Since light is a clean energy source, aqueous photocatalytic systems driven by solar light can be good representatives of green chemistry.
Via utilization of water-soluble out-of-plane (SAT) metalloporphyrins, photocatalytic systems exploiting solar energy in the visible range can be realized. In-plane metalloporphyrins which can be photochemically reduced to also photoactive SAT complexes can also be applied in such catalytic systems, increasing the feasibility of this concept.

Summary and aims of the research for the public
Describe here the major aims of the research for an audience with average background information. This summary is especially important for NRDI Office in order to inform decision-makers, media, and others.
Metalloporphyrins such as chlorophylls play very important roles in nature, but their advantageous photochemical properties can also be exploited in artificial photocatalytic systems utilizing visible light. Water-soluble sitting-atop (SAT) metalloporphyrins containing large-diameter metal ions located out of the plane of the porphyrin ligand exhibit unique photochemistry, offering the possibilities of their application as catalysts in cyclic processes for synthesis of special chemicals or compounds storing solar energy. The main goal of the proposed project is the elucidation of the mechanism of these reactions, and, on the basis of this knowledge, realization of catalytic systems utilizing both out-of-plane and also in-plane porphyrin complexes for preparative or photochemical water-splitting procedures. These systems may be key units of environmentally benign future technologies driven by solar light as renewable energy.

Final report

Results in Hungarian

Mind labilis (egyensúlyban létező) „out-of-plane” (OOP), mind kinetikailag inert „in-plane” metallo-porfirinek átfogó szerkezeti, képződési (kinetikai), fotofizikai és –kémiai vizsgálatát végeztük. Elméleti (DFT) számításokkal megállapítottuk, hogy – összhangban a lantanoida-kontrakció alapján várt tendenciával – az anionos 5,10,15,20-tetrakisz(4-szulfonatofenil)porfirinnel képezett lantanoida(III)-komplexek stabilitási állandói, mind az1:1, mind a 3:2 (fém:porfirin) összetétel esetében, csökkennek a fémion sugarának növekedtével – a fémion egyre nagyobb síkon kívüli távolsága miatt. Ugyanezen okból viszont a döntően irreverzibilis redoxi (MLCT) reakciót előidéző fotolízisük hatékonysága nő a kedvezményezett töltésszétválás miatt. A 3:2 összetételű biszporfirin komplex szerkezetére fotofizikai mérésekből következtettünk. Kinetikailag inert, kationos 5,10,15,20-tetrakis(1-methyl-4-pyridinium)porphyrinnel képezett Mn(III)-, Co(III)- és Ni(II)-komplexekkel fotokatalitikus ciklusokat képeztünk, melyek trietanolamin elektrondonor jelenlétében metilviologén gyökkationt generáltak, ami alkalmas vízből hidrogénfejlesztésre. Kimutattuk, hogy a Mn(III)- és Co(III)-komplexek ciklusa jelentősen eltér a Ni(II)-porfirinétől; előbbiek két, utóbbi egy fotokémiai lépésben közvetíti az elektront az akceptornak. Mn(III) anionos és kationos (felületaktív) porfirin-komplexét is alkalmaztuk szerves vegyületek fotokatalitikus oxidatív funkcionalizálása ill. lebontására.

Results in English

Comprehensive structural, kinetic, photophysical and –chemical study of both labile out-of-plane and kinetically inert in-plane metalloporphyrins was accomplished. DFT calculations established that – in accordance with the expectations due to the lanthanide contraction – the stability constants of lanthanide(III) complexes with 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin, for both 1:1 and 3:2 (metal:ligand) compositions, decrease upon increasing ionic radius of the metal center, because of the increasing out-of-plane distance of Ln(III). For the same reason, the efficiency of their photolysis causing predominantly irreversible redox (MLCT) reaction increases, due to the favored charge separation. The structure of the 3:2 bisporphyrin complexes was concluded from photophysical results. Photocatalytic cycles were realized by application of kinetically inert Mn(III), Co(III) and Ni(II) complexes with cationic 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin, which generated methylviologen radical cations in the presence of TEOA electrondonor. These radicals are applicable for hydrogen evolution from water. The cycle of the Mn(III) and Co(III) complexes was shown to significantly differ from that of the Ni(II) porphyrin; the previous ones transfer the electron tho the acceptor in two steps, while the latter species in a single one. Both anionic and (amphiphilic) cationic Mn(III) porphyrins were applied for oxygenation and oxidative degradation of organic compounds.

Full text

https://www.otka-palyazat.hu/download.php?type=zarobeszamolo&projektid=107310

Decision

Yes

List of publications

Major MM: Fotokatalitikus nikkel-porfirin rendszer átfogó jellemzése, TDK dolgozat, Pannon Egyetem, Veszprém, 2015

Valicsek M; Imran M; Horváth O: Photoinduced properties of water-soluble porphyrin complexes of early lanthanide(III) ions, Central European Conference on Photochemistry, Abstract Book, Bad Hofgastein, Austria, February 14-18, P16, p. 61, 2016

Valicsek Z; Imran M; Horváth O: Photophysical and photochemical investigation of water-soluble, anionic erbium(III) porphyrins, Central European Conference on Photochemistry, Abstract Book, Bad Hofgastein, Austria, February 14-18, P18, p. 63, 2016

Valicsek Z; Kiss MP; Kovács M; Horváth O: Spectrophotometric study about the acetato- and fluoro-complexes of early lanthanide(III) ions, Central European Conference on Photochemistry, Abstract Book, Bad Hofgastein, Austria, February 14-18, P20, p. 65, 2016

Fodor MA; Horváth O; Szabó P; Horváth K: Free-base and manganese(III) alkyl-pyridinium porphyrins in homogeneous and heterogeneous photooxidative systems, Central European Conference on Photochemistry, Abstract Book, Bad Hofgastein, Austria, February 14-18, P21, p. 66, 2016

Imran M: Formation, photophysics and photochemistry of water-soluble lanthanide(III) porphyrins, PhD Dissertation, University of Pannonia, 2016

Horváth O; Valicsek Z; Fodor MA; Major MM; Imran M; Grampp G; Wankmüller A: Visible light-driven photophysics and photochemistry of water-soluble metalloporphyrins, Coordination Chemistry Reviews, 325, 59-66, 2016

Fodor MA; Horváth O; Fodor L; Vazdar K; Grampp G; Wankmüller A: Photophysical and photochemical properties of manganese complexes with cationic porphyrin ligands: effects of alkyl substituents and micellar environment, Journal of Photochemistry and Photobiology A: Chemistry, 328, 233-239, 2016

Major MM; Horváth O; Fodor MA; Fodor L; Valicsek Z; Grampp G; Wankmüller A: Photophysical and photocatalytic behavior of nickel(II) 5,10,15,20-tetrakis(1-methylpyridinium-4- yl)porphyrin, Inorganic Chemistry Communications, 73, 1-3, 2016

Kiss MP; Imran M; Valicsek Z; Horváth O: Spectrophotometric investigation of early lanthanide(III) porphyrins for potential biomedical applications, XV. Italian-Hungarian Symposium on Spectrochemistry; Pharmacological research and analytical approaches, Abstract Book, Pisa, Italy, June 12-16, p. 160-161, 2016

Valicsek Z; Harrach G; Sebestyén AK; Németh B; Horváth O: Formation and photoinduced properties of silver porphyrins as promising PDT reagents, XV. Italian-Hungarian Symposium on Spectrochemistry; Pharmacological research and analytical approaches, Abstract Book, Pisa, Italy, June 12-16, p. 143-144, 2016

Valicsek Z; Horváth O: Possible application of out-of-plane metalloporphyrins in medical sciences, XV. Italian-Hungarian Symposium on Spectrochemistry; Pharmacological research and analytical approaches, Abstract Book, Pisa, Italy, June 12-16, OS6/2, p. 103-1044, 2016

Kiss MP; Valicsek Z; Horváth O: Korai lantanoida-porfirin komplexek szerkezetének és képződésének érdekességei, 50. Komplexkémiai Kollokvium, Kiadvány, Balatonvilágos, május 30 – június 1., E20, 2016

Valicsek Z; Sebestyén AK; Németh B; Harrach G; Horváth O: Az ionerősség és az axiális ligandum hatása a vízoldható ezüst-porfirin komplexek képződésére és oligomerizációjára, 50. Komplexkémiai Kollokvium, Kiadvány, Balatonvilágos, május 30 – június 1., E26, 2016

Valicsek Z; Kiss MP; Eller G; Szentgyörgyi C; Horváth O: Oligomerization of water-soluble lanthanide porphyrins, Book of Abstracts,1st Symposium on Weak Molecular Interactions, Pécs, March 5-6, p. 70, 2013

Valicsek Z; Horváth O: Formation of water-soluble cadmium porphyrin complexes: the effects of predistortion and the axial ligand, Book of Abstracts, Debrecen Colloquium on Inorganic Reaction Mechanisms 2013, Debrecen, June 11-15, L24, 2013

Valicsek Z; Patonay K; Horváth O: Formation of water-soluble bismuth(III) porphyrins: the role of the ligand’s charge, Book of Abstracts, Debrecen Colloquium on Inorganic Reaction Mechanisms 2013, Debrecen, June 11-15, P21, 2013

Fodor MA; Horváth O: Vízoldható mangán- és kobalt-porfirin komplexek fotokémiai és fotofizikai tulajdonságai, Környezetbarát anyagok és technológiák / 56. Magyar Spektrokémiai Vándorgyűlés, Veszprém, 2013. július 1-3., BT1, 2013

Kiss MP; Valicsek Z; Horváth O: Szamárium(III)ion és vízoldható, anionos porfirin reakciójának vizsgálata spektrofotometriás módszerrel, Környezetbarát anyagok és technológiák / 56. Magyar Spektrokémiai Vándorgyűlés, Veszprém, 2013. július 1-3., BT3), 2013

Horváth O; Valicsek Z; Fodor MA: Photophysical and photochemical properties of water-soluble metalloporphyrins in homogeneous and microheterogeneous systems, 20th International Symposium on Photophysics and Photochemistry of Coordination Compounds, Abstract Book, Traverse City, Michigan, July 7-11, CL-2, 2013

Horváth O; Valicsek Z: Singlet-1 fluorescence of porphyrins; the effects of metal ion’s position compared to the ligand plane, 20th International Symposium on Photophysics and Photochemistry of Coordination Compounds, Abstract Book, Traverse City, Michigan, July 7-11, P49, 2013

Valicsek Z; Horváth O: Formation kinetics of water-soluble metalloporphyrins, 4th International Conference on Chemical Kinetics, Abstract Book, Seville, Spain, July 8-12, O79, 2013

Valicsek Z; Kiss MP, Szentgyörgyi C; Horváth O: Kinetic investigation of the reaction between lanthanide ions and anionic porphyrins, 4th International Conference on Chemical Kinetics, Abstract Book, Seville, Spain, July 8-12, P34, 2013

Habuš I; Fodor MA; Horváth O; Fodor L: Amphiphilic cationic porphyrins: photophysical and photochemical properties of their manganese and cobalt complexes, 44th World Chemistry Congress, Abstract Book, Istanbul, Turkey, August 11-16, PC-P-01, p. 336, 2013

Vuk D; Kikaš I; Molčanov K; Horváth O;* Škorić I*: Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic oxygenation of thiophene and furan derivatives, Organic Biomolecular Chemistry (submitted), 2013

Horváth O; Valicsek Z, Fodor MA; Imran M; Fodor L; Grampp G; Rasmussen K; Habuš I: Photocatalytic properties of water-soluble metalloporphyrins in homogeneous and microheterogeneous systems, 3rd European Symposium on Photocatalysis , Abstract Book, Portorož, Slovenia, September 25-27, P1-3, 2013

Horváth O; Valicsek Z; Fodor MA; Imran M; Fodor L; Grampp; Wankmüller A; Habuš I: Photoinduced behavior of water-soluble metalloporphyrins in homogeneous and microheterogeneous systems, Central European Conference on Photochemistry 2014, Abstract Book, Bad Hofgastein, Austria, February 9-13, O16, p. 32, 2014

Fodor MA; Horváth O; Fodor L; Grampp G; Wankmüller A; Habuš I: Photochemical properties of water-soluble manganese(III) and cobalt(III) porphyrins in homogeneous and microheterogeneous systems, Central European Conference on Photochemistry 2014, Abstract Book, Bad Hofgastein, Austria, February 9-13, P26, p. 69, 2014

Imran M; Valicsek Z; Horváth O: Photophysical and photochemical investigation of water-soluble, anionic cerium(III) porphyrins, Central European Conference on Photochemistry 2014, Abstract Book, Bad Hofgastein, Austria, February 9-13, P28, p. 71, 2014

Kiss MP; Valicsek Z; Horváth O: Kinetic investigation of reactions between samarium(III) and an anionic porphyrin, European Colloquium on Inorganic Reaction Mechanisms, Abstract Book, 17-20 June, Debrecen, Hungary, P22, p. 68, 2014

Valicsek Z; Horváth O: Theoretical study on the geometrical and electronic structure of out-of-plane metalloporphyrins, 8th International Conference on Porphyrins and Phthalocyanines, Abstract Book, Istanbul, Turkey, June 22-27, COPF-4-5, p. 395, 2014

Valicsek Z; Horváth O: Distortion as the real origin of hyper-porphyrin spectra, 8th International Conference on Porphyrins and Phthalocyanines, Abstract Book, Istanbul, Turkey, June 22-27, S46-015, p. 739, 2014

Horváth O; Valicsek Z; Fodor MA; Imran M; Major MM; Grampp G; Wankmüller A: In-plane and out-of-plane water-soluble metalloporphyrins as photocatalysts for utilization of visible light, 20th International Conference on Photochemical Conversion of Solar Energy (IPS-20), Abstract Book,July 27 – August 1, Berlin, Germany, E3-4, p. 65, 2014

Horváth, O; Imran M; Valicsek Z: Photophysical and photochemical investigation of water-soluble, anionic neodymium(III) porphyrins, 20th International Conference on Photochemical Conversion of Solar Energy (IPS-20), Abstract Book, July 27 – August 1, Berlin, Germany, PoT 75, p. 157, 2014

Valicsek Z; Horváth O: Különböző típusú porfirin-komplexek képződése, 48. Komplexkémiai Kollokvium, Kivonatok, Siófok, május 28-30. E12, 2014

Kiss MP; Valicsek Z; Horváth O: Szamárium(III)-porfirinek képződésének reakciókinetikai vizsgálata vizes közegben spektrofotometriás módszerrel, I. Vízkémiai és technológiai konferencia, valamint 57. Magyar Spektrokémiai Vándorgyűlés, Veszprém, július 7-9. MS2, 2014

Kiss MP; Imran M; Szentgyörgyi C; Valicsek Z*; Horváth O: Peculiarities of the reactions between early lanthanide(III) ions and an anionic porphyrin, Inorganic Chemistry Communications 48, 22–25, 2014

Kiss MP; Valicsek Z; Horváth O: Szamárium(III)-porfirinek képződésének reakciókinetikai vizsgálata, XXXVII. Kémiai Előadói Napok, Program és előadás –összefoglalók, Szeged, nov. 3-5. 135-136. o., 2014

Ottó Horváth O; Valicsek Z; Fodor MA; Major MM; Imran M; Günter Grampp G; Wankmüller A: Water-soluble metalloporphyrins as photocatalysts for utilization of visible light, 12th Pannonian Symposium on Catalysis, Abstract Book, September 16-20, Třešť, Czech Republic, O38, 2014

Imran M; Valicsek Z; Horváth O: Photophysical and photochemical investigation of water-soluble porphyrin complexes of early lanthanide(III) ions, 16th Blue Danube Symposium on Heterocyclic Chemistry, Abstract Book, Balatonalmádi, Hungary, June 14-17, P26, p. 82, 2015

Fodor MA; Horváth O; Fodor L; Grampp G; Wankmüller A: Photophysical and photocatalytic behavior of cobalt(III) 5,10,15,20-tetrakis(1-methylpyridinium-4-yl)porphyrin, Inorganic Chemistry Communications 50, 110-112, 2014

Imran M; Szentgyörgyi C; Eller G; Valicsek Z; Horváth O: Peculiar photoinduced properties of water-soluble, early lanthanide(III) porphyrins, Inorganic Chemistry Communications 52, 60-63, 2015

Vuk D; Horváth O; Marinić Ž; Škorić I: Functionalization of the benzobicyclo[3.2.1]octadiene skeleton possessing one isolated double bond via photocatalytic oxygenation, Tetrahedron (beküldve), 2015

Imran M; Jurecska T; Kiss MP; Valicsek Zs; Horváth O: Formation, photophysics and photochemistry of water-soluble samarium(III) porphyrins, 16th Blue Danube Symposium on Heterocyclic Chemistry, Abstract Book, Balatonalmádi, Hungary, June 14-17, P27, p. 83, 2015

Kiss MP; Patona K; Valicsek Z; Horváth O: Transformation reactions of p-type hyper-porphyrins in water, 16th Blue Danube Symposium on Heterocyclic Chemistry, Abstract Book, Balatonalmádi, Hungary, June 14-17, P32, p. 88, 2015

Kiss MP; Valicsek Z; Horváth O: Kinetic investigation of the formation of samarium(III) and neodymium(III) porphyrins, 16th Blue Danube Symposium on Heterocyclic Chemistry, Abstract Book, Balatonalmádi, Hungary, June 14-17, P31, p. 87, 2015

Fodor MA; Major MM; Horváth O; Grampp G; Wankmüller A: Water-soluble free-base and metalloporphyrins utilized in various photocatalytic systems, 16th Blue Danube Symposium on Heterocyclic Chemistry, Abstract Book, Balatonalmádi, Hungary, June 14-17, P18, p. 74, 2015

Valicsek Z; Kiss MP; Imran M; Horváth O: Peculiarities of the reactions between early lanthanide(III) ions and an anionic porphyrin, 9th International Conference on Chemical Kinetics, Abstract Book, Ghent, Belgium, June 28 – July 2, O79, p. 281, 2015

Valicsek Z; Patonay K; Horváth O: The role of water and the ligand’s charge in the formation kinetics of bismuth(III) porphyrins, 9th International Conference on Chemical Kinetics, Abstract Book, Ghent, Belgium, June 28 – July 2, P50, p. 499, 2015

Kiss MP; Valicsek Z; Horváth O: Effects of axial ligands on the formation kinetics of water-soluble samarium (III) porphyrins, 9th International Conference on Chemical Kinetics, Abstarct Book, Ghent, Belgium, June 28 – July 2, P49, p. 497, 2015

Horváth O; Valicsek Z; Fodor MA; Major MM; Imran M; Grampp G; Wankmüller A: Utilization of water-soluble metalloporphyrins in visible light-driven photochemical systems, 21st International Symposium on the Photochemistry and Photophysics of Coordination Compounds, Abstract Book, Krakow, Poland, July 5-9, KL10, p. 47, 2015

Horváth O; Major MM; Fodor MA; Valicsek Z; Fodo L; Grampp G; Wankmüller A: Photophysical and photochemical behaviour of a cationic nickel(II) porphyrin, 21st International Symposium on the Photochemistry and Photophysics of Coordination Compounds, Abstract Book, Krakow, Poland, July 5-9, PP36, p.127, 2015

Valicsek Z; Horváth O: Study about the triplet-1 state of anionic metalloporphyrins, 21st International Symposium on the Photochemistry and Photophysics of Coordination Compounds, Abstract Book, Krakow, Poland, July 5-9, PP135, p. 226, 2015

Imran M; Valicsek Z; Horváth O: Photophysical and photochemical investigation of water-soluble, anionic dysprosium(III) porphyrins, 21st International Symposium on the Photochemistry and Photophysics of Coordination Compounds, Abstarct Book, Krakow, Poland, July 5-9, PP41, p. 132, 2015

Fodor MA; Horváth O; Szabó P; Horváth K: Photophysical and photocatalytic properties of water-soluble free-base and manganese(III) porphyrins, The 21st International Symposium on the Photochemistry and Photophysics of Coordination Compounds, Abstract Book, Kraków, July 5-9, PP028, p. 119, 2015

Valicsek Z; Kiss MP; Imran M; Szentgyörgyi C; Eller G; Jurecska T; Törőcsik R; Horváth O: Vízoldható, lantanoida(III)-porfirin komplexek képződésének és fotoindukált tulajdonságainak érdekességei, 49. Komplexkémiai Kollokvium, Előadás-összefoglalók, Siófok, május 26-28. E9, 2015

Major MM; Horváth O; Fodor MA; Valicsek Z; Fodor L: Kationos nikkel(II)-porfirin fotofizikai és fotokémiai tulajdonságainak vizsgálata, MKE 2. Nemzeti Konferencia, Program és előadás-összefoglalók, Hajdúszoboszló, augusztus 31 – szeptember 2. FK-O-24, 46. o, 2015

Kiss MP; Imran M; Valicsek Z; Horváth O: Vízoldható neodímium(III)-porfirinek képződésének spektrofotometriai és reakciókinetikai vizsgálata, MKE 2. Nemzeti Konferencia, Progrem és előadás-összefoglalók, Hajdúszoboszló, augusztus 31 – szeptember 2. A-O-16, 92. o., 2015

Valicsek Z; Horváth O: A fémion helyzetének hatása a porfirin-komplexek szingulett-1 fluoreszcenciájára, MKE 2. Nemzeti Konferencia, Program és előadás-összefoglalók, Hajdúszoboszló, augusztus 31 – szeptember 2. A-P-7, 200. o., 2015

Valicsek Z; Imran M; Kiss MP; Szentgyörgyi C; Eller G; Jurecska T; Törőcsik R; Horváth O: Vízoldható, korai lantanoida(III)-porfirin komplexek fotoindukált tulajdonságainak vizsgálata, MKE 2. Nemzeti Konferencia, Program és előadás-összefoglalók, Hajdúszoboszló, augusztus 31 – szeptember 2. FK-O-23, 45. o., 2015

Fodor MA; Horváth O; Fodor L; Horváth K; Szabó P: Vízoldható mangán(III)-porfirinek fotofizikai tulajdonságia és fotokatalitikus alkalmazása, MKE 2. Nemzeti Konferencia, Program és előadás-összefoglalók, Hajdúszoboszló, augusztus 31.- szeptember 2. FK-P-3, 165. o., 2015

Kiss MP; Patonay K; Valicsek Z; Horváth O: Transformation reactions of p-type hyper-porphyrins in water, 16th Blue Danube Symposium on Heterocyclic Chemistry, Abstract Book, Balatonalmádi, Hungary, June 14-17, P32, p. 88, 2015

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