Abstract
In this study, firstly, a new phthalonitrile derivative was synthesized from the reaction of caffeic acid with phthalonitrile. Then, metal phthalocyanine complexes were obtained from the reaction of this phthalonitrile derivative with metal salts. Compounds were characterized by UV, NMR, IR and Mass spectroscopy methods. In addition, the fluorescence and electronic properties of the diamagnetic zinc phthalocyanine compound were investigated. The performances of dye-sensitized solar cells of compounds were examined. The calculated power conversion efficiencies (η %) of the complexes using the obtained current density (J)-voltage (V) curves were determined that these compounds can be used as promising sensitizers in solar cell applications. The calculated power conversion efficiencies (% η) of the complexes were found to be at a reasonable level. Molecular orbital properties such as HOMO–LUMO energy gap, Fermi Energies, state density spectrum, and molecular electrostatic potential surfaces were calculated for each phthalocyanine molecule. In addition, the amount of phthalocyanine required for ideal dye sensitivity was investigated.
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References
Ağırtaş MS (2007) Synthesis and characterization of novel symmetrical phthalocyanines substituted with four benzo [d] [1,3] dioxol-5-ylmethoxy groups. Inorganica Chim Acta 360(7):2499–2502. https://doi.org/10.1016/j.ica.2006.12.029
Ağırtaş MS (2020) Fluorescence properties in different solvents and synthesis of axially substituted silicon phthalocyanine bearing bis-4-tritylphenoxy units. J Heterocycl Commun 26(1):130–136. https://doi.org/10.1515/hc-2020-0113
Ağırtaş MS, Cabir B, Yıldıko Ü, Özdemir S, Gonca S (2021) Synthesis, antioxidant, DNA cleavage and antimicrobial properties of phthalocyanine complexes bearing the poly-hydroxyl groups. Chem Pap 75(4):1749–1760. https://doi.org/10.1007/s11696-020-01432-7
Agırtaş MS, Güngördü Solğun D, Yildiko Ü, Özkartal A (2020) Design of novel substituted phthalocyanines; synthesis and fluorescence, DFT, photovoltaic properties. Turk J Chem 44:1574–1586
Amitha GS, Ameen MY, Reddy VS, Vasudevan S (2019) Synthesis of peripherally tetra substituted neutral azophenoxy zinc phthalocyanine and its application in bulk hetero junction solar cells. J Mol Struct 1185:425–431. https://doi.org/10.1016/j.molstruc.2019.02.086
Arslantas A, Agirtas MS (2018) Investigation of DNA binding activities of peripherally 2,10,16,24-Tetrakis Dimethyl 5-(Phenoxy)-Isophthalate-Substituted Ni(II) Phthalocyanine complex. ChemistrySelect 3(11):3155–3160. https://doi.org/10.1002/slct.201800572
Attia MS, Ali K, El-Kemary M, Darwish WM (2019) Phthalocyanine-doped polystyrene fluorescent nanocomposite as a highly selective biosensor for quantitative determination of cancer antigen 125. Talanta 201:185–193. https://doi.org/10.1016/j.talanta.2019.03.119
Cabir B, Yildiko U, Ağirtaş MS (2019) Synthesis, DFT analysis, and electronic properties of new phthalocyanines bearing ETAEO substituents on peripheral position. J Coord Chem 72(17):2997–3011. https://doi.org/10.1080/00958972.2019.1680832
Cabir B, Yildiko U, Ağırtaş MS, Horoz S (2020) Computational DFT calculations, photovoltaic properties and synthesis of (2R, 3S)-2, 3, 4-trihydroxybutoxy substituted phthalocyanines. Inorg Nano-Met Chem 50(9):816–827. https://doi.org/10.1080/24701556.2020.1725051
Cozzolino M, Pesce L, Pezzuoli D, Montali C, Brancaleon L, Cavanna L, Abbruzzetti S, Diaspro A, Bianchini P, Viappiani C (2019) Apomyoglobin is an efficient carrier for zinc phthalocyanine in photodynamic therapy of tumors. Biophys Chem 253:106228. https://doi.org/10.1016/j.bpc.2019.106228
Frisch MJ, GAUSSIAN09. http://www.gaussian.com/.
Ghadari R, Saei P-S, Sabri A, Ghasemi Z and Kong F, (2020). Enhanced phthalocyanine-sensitized solar cell efficiency via cooperation of nitrogen-doped carbon dots. J Clean Prod 2020 v.268. DOI: https://doi.org/10.1016/j.jclepro.2020.122236
Güngördü Solğun D, Horoz S, Ağırtaş MS (2018) Synthesis of novel tetra (4-tritylphenoxy) substituted metallophthalocyanines and investigation of their aggregation, photovoltaic, solar cell properties. Inorg Nano-Met Chem 48(10):508–514. https://doi.org/10.1080/24701556.2019.1572624
Janas K, Boniewska-Bernacka E, Dyrda G, Słota R (2021) Porphyrin and phthalocyanine photosensitizers designed for targeted photodynamic therapy of colorectal cancer. Bioorg Med Chem 30:115926. https://doi.org/10.1016/j.bmc.2020.115926
Kong S, Wang X, Bai L, Song Y, Meng F (2019) Multi-arm ionic liquid crystals formed by pyridine-mesophase and copper phthalocyanine. J Mol Liq 288:111012. https://doi.org/10.1016/j.molliq.2019.111012
Li B, Wei P, de Leon A, Frey T, Pentzer E (2017) Polymer composites with photo-responsive phthalocyanine for patterning in color and fluorescence. Eur Polym J 89:399–405. https://doi.org/10.1016/j.eurpolymj.2017.02.042
Lin K-C, Doane T, Wang L, Li P, Pejic S, Kenney ME, Burda C (2014) Laser spectroscopic assessment of a phthalocyanine-sensitized solar cell as a function of dye loading. Sol Energy Mater Sol Cells 126:155–162. https://doi.org/10.1016/j.solmat.2014.03.025
Luo S, Zhang E, Su Y, Cheng T, Shi C (2011) A review of NIR dyes in cancer targeting and imaging. Biomaterials 32(29):7127–7138. https://doi.org/10.1016/j.biomaterials.2011.06.024
Maidur SR, Patil PS, Rao SV, Shkir M, Dharmaprakash SM (2017) Experimental and computational studies on second-and third-order nonlinear optical properties of a novel D-π-A type chalcone derivative: 3-(4-methoxyphenyl)-1-(4-nitrophenyl) prop-2-en-1-one. Opt Laser Technol 97:219–228. https://doi.org/10.1016/j.optlastec.2017.07.003
Martín-Gomis L, Parejo C, Álvarez JC, Fernández-Lázaro F, Sastre-Santos Á (2017) Dye sensitized solar cells (DSSCs) based on bulky tert-octylphenoxy-carboxyphenyl substituted phthalocyanine without the presence of co-adsorbents. Inorganica Chim Acta 468:327–333. https://doi.org/10.1016/j.ica.2017.07.043
Matshitse R, Nwaji N, Mananga M, Prinsloo E, Nyokong TJJoP and A-chemistry P, (2018). Effect of number of positive charges on the photophysical and photodynamic therapy activities of quarternary benzothiazole substituted zinc phthalocyanine. 367: 253-260.
Moghadam G, Tirgir F, Reshak AH, Khorshidi M (2019) Specific features of 3, 6-bis (4-hydroxy phenyl)-piperazine-2, 5-dione (BHPPD) diphenolic monomer and compered with toxic industrial bisphenol-A (BPA): DFT calculation. Mater Chem Phys 236:121780. https://doi.org/10.1016/j.matchemphys.2019.121780
Mumit MA, Pal TK, Alam MA, Islam MA-A-A-A, Paul S, Sheikh MC (2020) DFT studies on vibrational and electronic spectra, HOMO–LUMO, MEP, HOMA, NBO and molecular docking analysis of benzyl-3-N-(2,4,5-trimethoxyphenylmethylene)hydrazinecarbodithioate. J Mol Struct 1220:128715. https://doi.org/10.1016/j.molstruc.2020.128715
O’Boyle NM, Tenderholt AL, Langner KM (2008) cclib: a library for package-independent computational chemistry algorithms. J Comput Chem 29(5):839–845. https://doi.org/10.1002/jcc.20823
O’Regan BC, López-Duarte I, Martínez-Díaz MV, Forneli A, Albero J, Morandeira A, Palomares E, Torres T, Durrant JR (2008) Catalysis of recombination and its limitation on open circuit voltage for dye sensitized photovoltaic cells using phthalocyanine dyes. J Am Chem Soc 130(10):2906–2907. https://doi.org/10.1021/ja078045o
Ou C, Lv W, Chen J, Yu T, Song Y, Wang Y, Wang S, Yang G (2021) Structural, photophysical and nonlinear optical limiting properties of sandwich phthalocyanines with different rare earth metals. Dyes Pigm 184:108862. https://doi.org/10.1016/j.dyepig.2020.108862
Özdemir M, Köksoy B, Yalçın B, Taşkın T, Selçuki NA, Salan Ü, Durmuş M, Bulut M (2021) Novel lutetium(III) phthalocyanine-coumarin dyads; synthesis, characterization, photochemical, theoretical and antioxidant properties. Inorganica Chim Acta 517:120145. https://doi.org/10.1016/j.ica.2020.120145
Panwar V, Kumar P, Ray SS, Jain SL (2015) Organic inorganic hybrid cobalt phthalocyanine/polyaniline as efficient catalyst for aerobic oxidation of alcohols in liquid phase. Tetrahedron Lett 56(25):3948–3953. https://doi.org/10.1016/j.tetlet.2015.05.003
Priya MK, Revathi BK, Renuka V, Sathya S, Asirvatham PS (2019) Molecular structure, spectroscopic (FT-IR, FT-Raman, 13C and 1H NMR) analysis, HOMO-LUMO energies, Mulliken, MEP and thermal properties of new chalcone derivative by DFT calculation. Mater Today 8:37–46. https://doi.org/10.1016/j.matpr.2019.02.078
Rad AS, Aghaei SM (2018) Potential of metal–fullerene hybrids as strong nanocarriers for cytosine and guanine nucleobases: a detailed DFT study. Curr Appl Phys 18(2):133–140. https://doi.org/10.1016/j.cap.2017.11.016
Rahuman MH, Muthu S, Raajaraman BR, Raja M, Umamahesvari H (2020) Investigations on 2-(4-Cyanophenylamino) acetic acid by FT-IR, FT-Raman, NMR and UV-Vis spectroscopy, DFT (NBO, HOMO-LUMO, MEP and Fukui function) and molecular docking studies. Heliyon 6(9):e04976. https://doi.org/10.1016/j.heliyon.2020.e04976
Reddy G, Gaspera ED, Jones LA, Giribabu L (2021) Self-assembly of a symmetrical dimethoxyphenyl substituted Zn(II) phthalocyanine into nanoparticles with enhanced NIR absorbance for singlet oxygen generation. J Photochem Photobiol 408:113123. https://doi.org/10.1016/j.jphotochem.2020.113123
Saka ET, Durmuş M, Kantekin H (2011) Solvent and central metal effects on the photophysical and photochemical properties of 4-benzyloxybenzoxy substituted phthalocyanines. J Organomet Chem 696(4):913–924. https://doi.org/10.1016/j.jorganchem.2010.10.024
Salih Ağırtaş M (2007) Non-aggregating phthalocyanines with bulky 2,4-di-tert-butylphenoxy-substituents. Dyes Pigm 74(2):490–493. https://doi.org/10.1016/j.dyepig.2006.03.009
Sherin DR, Manojkumar TK (2020) Significance of five membered heterocycles in fine tuning of HOMO-LUMO gap of simple donor-acceptor system as organic solar cell material: a DFT approach. Mater Today 33:1229–1233. https://doi.org/10.1016/j.matpr.2020.03.482
Shukla BK and Yadava U, (2020). DFT calculations on molecular structure, MEP and HOMO-LUMO study of 3-phenyl-1-(methyl-sulfonyl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine. Mater Today. https://doi.org/10.1016/j.matpr.2020.10.903
Singh K, bala I and Kataria R, (2020) Crystal structure, Hirshfeld surface and DFT based NBO, NLO, ECT and MEP of benzothiazole based hydrazone. Chem Phys 538:110873. https://doi.org/10.1016/j.chemphys.2020.110873
Suzuki A, Okumura H, Yamasaki Y, Oku T (2019) Fabrication and characterization of perovskite type solar cells using phthalocyanine complexes. Appl Surf Sci 488:586–592. https://doi.org/10.1016/j.apsusc.2019.05.305
Urbani M, Ragoussi M-E, Nazeeruddin MK, Torres T (2019) Phthalocyanines for dye-sensitized solar cells. Coord Chem Rev 381:1–64. https://doi.org/10.1016/j.ccr.2018.10.007
Wu S, Liu Q, Zheng Y, Li R, Peng T (2017) An efficient copper phthalocyanine additive of perovskite precursor for improving the photovoltaic performance of planar perovskite solar cells. J Power Sources 359:303–310. https://doi.org/10.1016/j.jpowsour.2017.05.083
Xu J, Yang W, Chen R (2020) The photovoltaic performance of highly asymmetric phthalocyanine-sensitized brookite-based solar cells. Optik 200:163413. https://doi.org/10.1016/j.ijleo.2019.163413
Yum JH, Jang SR, Humphry-Baker R, Grätzel M, Cid JJ, Torres T, Nazeeruddin MK (2008) Effect of coadsorbent on the photovoltaic performance of zinc pthalocyanine-sensitized solar cells. Langmuir : The ACS J Surf Colloids 24(10):5636–5640. https://doi.org/10.1021/la800087q
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We would like to thank Van Yüzüncü Yıl University Scientific Research Projects Unit for their contribution (Project Number: FDK-2019-8105).
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Güngördü Solğun, D., Yıldıko, Ü., Özkartal, A. et al. Photovoltaic performance properties, DFT studies, and synthesis of (E)-3-(diphenxy) acrylic acid substituted phthalocyanine complexes. Chem. Pap. 75, 6285–6295 (2021). https://doi.org/10.1007/s11696-021-01786-6
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DOI: https://doi.org/10.1007/s11696-021-01786-6