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Sono-Fotokimyasal Yöntemle Arttırılmış Singlet Oksijen Oluşumuna Sahip Yeni Furan-İmin Sübstitüeli Çinko Ftalosiyanin

Year 2025, Volume: 29 Issue: 1, 44 - 53, 25.04.2025
https://doi.org/10.19113/sdufenbed.1599212

Abstract

Bu çalışma, furan-imin sübstitüentine sahip yeni çinko ftalosiyaninin (3) fotokimyasal ve sonofotokimyasal özellikleri arasındaki ilişkiyi, kompleksin sentezi ve karakterizasyonu ile birlikte göstermeyi amaçlamaktadır. Kompleksin (3) DMSO'daki singlet oksijen kuantum verimini hesaplamak ve karşılaştırmak için hem fotokimyasal hem de sono-fotokimyasal teknikler uygulandı. Kompleksin (3) singlet oksijen kuantum verimini hesaplamak ve karşılaştırmak için hem fotokimyasal hem de sono-fotokimyasal teknikler uygulanmıştır. Kompleksin (3) singlet oksijen kuantum verimi PDT yöntemi (sadece ışık ışınlaması) ile 0.12 olarak hesaplanmış iken, bu değer SPDT yöntemi (ışık ve ultrasonun kombinasyonu) ile 0.78'e çıkarılmıştır. Singlet oksijen üretim verimliliği göz önüne alındığında, SPDT yönteminin PDT yönteminden daha güçlü bir terapötik yaklaşım olduğu ve ayrıca kompleksin (3) hem PDT hem de SPDT uygulamalarında uygun bir sono/fotosensitizer adayı olabileceği söylenebilir. Bu çalışma aynı zamanda, SPDT yöntemini kullanarak singlet oksijen üretimini artırmaya yönelik alana katkıda bulunacaktır.

References

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  • [2] Nas A, Kahriman N, Kantekin H, Yaylı N, Durmuş M. The synthesis of novel unmetallated and metallated phthalocyanines including (E)-4-(3-cinnamoylphenoxy) groups at the peripheral positions and photophysicochemical properties of their zinc phthalocyanine derivatives. Dyes and Pigments. 2013;99(1):90-8.
  • [3] Wysocki M, Ziental D, Biyiklioglu Z, Jozkowiak M, Baş H, Dlugaszewska J, et al. Non-peripheral octasubstituted zinc (II) phthalocyanines bearing pyridinepropoxy substituents–Antibacterial, anticancer photodynamic and sonodynamic activity. Journal of Inorganic Biochemistry. 2025;262:112751.
  • [4] Khoza P, Antunes E, Nyokong T. Synthesis and photophysicochemical properties of zinc phthalocyanine derivatized with benzothiazole or carbazole photosensitizers. Polyhedron. 2013;61:119-25.
  • [5] Chen J, Chen Z, Zheng Y, Zhou S, Wang J, Chen N, et al. Substituted zinc phthalocyanine as an antimicrobial photosensitizer for periodontitis treatment. Journal of Porphyrins and Phthalocyanines. 2011;15(04):293-9.
  • [6] Sağlam Ö, Farajzadeh N, Yaşa Atmaca G, Erdoğmuş A, Koçak MB. Effect of position and connected atom on photophysical and photochemical properties of some fluorinated metallophthalocyanines. Photochemistry and Photobiology. 2021;97(2):270-7.
  • [7] Al-Raqa SY, Köksoy B, Durmuş M. A novel lutetium (III) acetate phthalocyanine directly substituted with N, N’-dimethylaminophenyl groups via CC bonds and its water-soluble derivative for photodynamic therapy. Tetrahedron letters. 2017;58(7):685-9.
  • [8] Kwiatkowski S, Knap B, Przystupski D, Saczko J, Kędzierska E, Knap-Czop K, et al. Photodynamic therapy–mechanisms, photosensitizers and combinations. Biomedicine & pharmacotherapy. 2018;106:1098-107.
  • [9] Atmaca GY, Erdoğmuş A. Synthesis of new water soluble silicon phthalocyanine substituted by linker sulfur atom and photophysicochemical studies for photodynamic therapy. Journal of Porphyrins and Phthalocyanines. 2019;23(11n12):1398-405.
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  • [11] Wan G-Y, Liu Y, Chen B-W, Liu Y-Y, Wang Y-S, Zhang N. Recent advances of sonodynamic therapy in cancer treatment. Cancer biology & medicine. 2016;13(3):325.
  • [12] Wang X, Zhong X, Bai L, Xu J, Gong F, Dong Z, et al. Ultrafine titanium monoxide (TiO1+ x) nanorods for enhanced sonodynamic therapy. Journal of the American Chemical Society. 2020;142(14):6527-37.
  • [13] Huang P, Qian X, Chen Y, Yu L, Lin H, Wang L, et al. Metalloporphyrin-encapsulated biodegradable nanosystems for highly efficient magnetic resonance imaging-guided sonodynamic cancer therapy. Journal of the American Chemical Society. 2017;139(3):1275-84.
  • [14] Nene LC, Sindelo A, Britton J, Nyokong T. Effect of ultrasonic frequency and power on the sonodynamic therapy activity of cationic Zn (II) phthalocyanines. Journal of Inorganic Biochemistry. 2021;217:111397.
  • [15] Borah BM, Cacaccio J, Durrani FA, Bshara W, Turowski SG, Spernyak JA, et al. Sonodynamic therapy in combination with photodynamic therapy shows enhanced long-term cure of brain tumor. Scientific Reports. 2020;10(1):21791.
  • [16] Canavese G, Ancona A, Racca L, Canta M, Dumontel B, Barbaresco F, et al. Nanoparticle-assisted ultrasound: A special focus on sonodynamic therapy against cancer. Chemical Engineering Journal. 2018;340:155-72.
  • [17] Can Karanlık C, Aguilar-Galindo F, Sobotta L, Guzel E, Erdogmus A. Combination of light and ultrasound: exploring sono–photochemical activities of phthalocyanine-based sensitizers. The Journal of Physical Chemistry C. 2023;127(19):9145-53.
  • [18] Atmaca GY, Aksel M, Bilgin MD, Erdoğmuş A. Comparison of sonodynamic, photodynamic and sonophotodynamic therapy activity of fluorinated pyridine substituted silicon phthalocyanines on PC3 prostate cancer cell line. Photodiagnosis and photodynamic therapy. 2023;42:103339.
  • [19] Alves F, Ayala ETP, Pratavieira S. Sonophotodynamic Inactivation: The power of light and ultrasound in the battle against microorganisms. Journal of Photochemistry and Photobiology. 2021;7:100039.
  • [20] Granados-Tavera K, Zambrano-Angulo M, Montenegro-Pohlhammer N, Atmaca GY, Sobotta L, Güzel E, et al. Synergistic effect of ultrasound and light to efficient singlet oxygen formation for photodynamic purposes. Dyes and Pigments. 2023;210:110986.
  • [21] Ogbodu RO, Nitzsche B, Ma A, Atilla D, Gürek AG, Höpfner M. Photodynamic therapy of hepatocellular carcinoma using tetra-triethyleneoxysulfonyl zinc phthalocyanine as photosensitizer. Journal of Photochemistry and Photobiology B: Biology. 2020;208:111915.
  • [22] Atmaca GY, Karanlık CC, Erdoğmuş A. Novel silicon phthalocyanines with improved singlet oxygen generation by Sono-photochemical applications. Journal of Photochemistry and Photobiology A: Chemistry. 2023;436:114365.
  • [23] Zheng Y, Ye J, Li Z, Chen H, Gao Y. Recent progress in sono-photodynamic cancer therapy: From developed new sensitizers to nanotechnology-based efficacy-enhancing strategies. Acta Pharmaceutica Sinica B. 2021;11(8):2197-219.
  • [24] Nene LC, Abrahamse H. Design consideration of phthalocyanines as sensitizers for enhanced sono-photodynamic combinatorial therapy of cancer. Acta Pharmaceutica Sinica B. 2024;14(3):1077-97.
  • [25] Ke M-R, Wang C, He Q, Que R, Wei Y, Zheng B-Y, et al. N-bridging tetra-substituted zinc (II) phthalocyanines with Q-band absorption up to 780 nm and eminent photosensitizing activities for photodynamic therapy. Dyes and Pigments. 2024;227:112169.
  • [26] Quartarolo AD, Lanzo I, Sicilia E, Russo N. Can phthalocyanines and their substituted α-para-(methoxy) phenyl derivatives act as photosensitizers in photodynamic therapy? A TD-DFT study. Physical Chemistry Chemical Physics. 2009;11(22):4586-92.
  • [27] Lo P-C, Rodríguez-Morgade MS, Pandey RK, Ng DK, Torres T, Dumoulin F. The unique features and promises of phthalocyanines as advanced photosensitisers for photodynamic therapy of cancer. Chemical Society Reviews. 2020;49(4):1041-56.
  • [28] Claessens CG, Hahn U, Torres T. Phthalocyanines: From outstanding electronic properties to emerging applications. The Chemical Record. 2008;8(2):75-97.
  • [29] Roguin LP, Chiarante N, Vior MCG, Marino J. Zinc (II) phthalocyanines as photosensitizers for antitumor photodynamic therapy. The international journal of biochemistry & cell biology. 2019;114:105575.
  • [30] Karanlık CC, Atmaca GY, Erdoğmuş A. Comparison of singlet oxygen production of ethyl vanillin substituted silicon phthalocyanine using sonophotodynamic and photodynamic methods. Journal of Molecular Structure. 2023;1274:134498.
  • [31] Burtsev I, Platonova YB, Volov A, Tomilova L. Synthesis, characterization and photochemical properties of novel octakis (p–fluorophenoxy) substituted phthalocyanine and its gallium and indium complexes. Polyhedron. 2020;188:114697.
  • [32] Calori IR, Tedesco AC. Aluminum chloride phthalocyanine in MCF-7: rationally accounting for state of aggregation of photosensitizers inside cells. Dyes and Pigments. 2020;173:107940.
  • [33] Oda K, Ogura S-i, Okura I. Preparation of a water-soluble fluorinated zinc phthalocyanine and its effect for photodynamic therapy. Journal of Photochemistry and Photobiology B: Biology. 2000;59(1-3):20-5.
  • [34] Yüzeroğlu M, Karaoğlan GK, Köse GG, Erdoğmuş A. Synthesis of new zinc phthalocyanines including schiff base and halogen; photophysical, photochemical, and fluorescence quenching studies. Journal of Molecular Structure. 2021;1238:130423.
  • [35] Roopa D, Shyamsunder K, Karunakar P, Rajabathar JR, Venkatesulu A, Karnan M, et al. Naphtho [2, 1-b] furan derived triazole-pyrimidines as highly potential InhA and Cytochrome c peroxidase inhibitors: synthesis, DFT calculations, drug-likeness profile, molecular docking and dynamic studies. Journal of Molecular Structure. 2023;1287:135685.
  • [36] Lehner V, Davies HM, Reiser O. Rh (II)-catalyzed cyclopropanation of furans and its application to the total synthesis of natural product derivatives. Organic letters. 2017;19(18):4722-5.
  • [37] Hithesh MC, Mohana KNS, Harsha YM, Sreelakshmi M, Madhusudhana AM, Kumar MCS. Effects of curing temperature and addition of functionalized graphene oxide on corrosion barrier performance of phenol furfural polymer-amino phenolic resin composite. Progress in Organic Coatings. 2024;188:108164.
  • [38] Güzel E, Şaki N, Akın M, Nebioğlu M, Şişman İ, Erdoğmuş A, et al. Zinc and chloroindium complexes of furan-2-ylmethoxy substituted phthalocyanines: Preparation and investigation of aggregation, singlet oxygen generation, antioxidant and antimicrobial properties. Synthetic Metals. 2018;245:127-34.
  • [39] Kahriman N, Ünver Y, Akçay HT, Gülmez AD, Durmuş M, Değirmencioğlu İ. Photophysical and photochemical study on novel axially chalcone substituted silicon (IV) phthalocyanines. Journal of Molecular Structure. 2020;1200:127132.
  • [40] Yarasir MN, Kandaz M, Güney O, Salih B. Synthesis and photophysical properties of metallophthalocyanines substituted with a benzofuran based fluoroprobe. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2012;93:379-83.
  • [41] Karanlık G, Ocak H, Eran BB. Imine based chiral liquid crystals: effect of varying the terminal substituent and orientation of ester linking unit. Journal of Molecular Liquids. 2019;275:567-77.
  • [42] Harmandar K, Saglam MF, Sengul IF, Ekineker G, Balcik-Ercin P, Göksel M, et al. Novel triazole containing zinc (II) phthalocyanine Schiff bases: Determination of photophysical and photochemical properties for photodynamic cancer therapy. Inorganica Chimica Acta. 2021;519:120286.
  • [43] Senge MO, Renner MW, Kallisch WW, Fajer J. Molecular structure of (5, 10, 15, 20-tetrabutyl-2, 3, 7, 8, 12, 13, 17, 18-octaethylporphyrinato) nickel (II)—correlation of nonplanarity with frontier orbital shifts. Journal of the Chemical Society, Dalton Transactions. 2000(3):381-5.
  • [44] Ünlü S, Elmalı FT, Atmaca GY, Erdoğmuş A. Synthesis of phenanthroline substituted five-nuclear phthalocyanine zinc complex and exploring of photochemical and sono-photochemical properties. Polyhedron. 2024;250:116817.
  • [45] Aydogdu S, Atmaca GY, Erdoğmuş A, Hatipoglu A. Synthesis of a new Zn-phthalocyanine, photophysical, photochemical, and sono-photochemical properties and DFT studies. Polyhedron. 2024;256:116989.
  • [46] Köse GG, Erdoğmuş A. Dual effect of light and ultrasound for efficient singlet oxygen generation with novel diaxial silicon phthalocyanine sensitizer. Photochemistry and Photobiology. 2024;100(1):52-66.
  • [47] Nyokong T. Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines. Coordination Chemistry Reviews. 2007;251(13-14):1707-22.

Novel Furan-Imine Substituted Zinc Phthalocyanine with Increased Singlet Oxygen Formation by Sono-Photochemical Method

Year 2025, Volume: 29 Issue: 1, 44 - 53, 25.04.2025
https://doi.org/10.19113/sdufenbed.1599212

Abstract

This work aims to show the relationship between photochemical and sonophotocehmical features of novel zinc phthalocyanine having furan-imine substituent along with synthesis and characterization of complex (3). Both photochemical and sono-photochemical techniques were applied in order to calculate and compare the singlet oxygen quantum yield of the complex (3) in DMSO. The singlet oxygen quantum yield of the complex (3) was determined as 0.12 by the PDT method (irradiated with only light), while the value of 0.78 was reached by the SPDT approach (combination of light and ultrasound). Considering the efficiency in singlet oxygen formation, it can be said that the SPDT modality is a more powerful therapeutic solution than the PDT technique and also the complex (3) may be a suitable sono/photosensitizer candidate in both PDT and SPDT tecniques. This study will also contribute to the field on enhancing singlet oxygen generation by using SPDT approach.

References

  • [1] Maree SE, Nyokong T. Syntheses and photochemical properties of octasubstituted phthalocyaninato zinc complexes. Journal of Porphyrins and Phthalocyanines. 2001;5(11):782-92.
  • [2] Nas A, Kahriman N, Kantekin H, Yaylı N, Durmuş M. The synthesis of novel unmetallated and metallated phthalocyanines including (E)-4-(3-cinnamoylphenoxy) groups at the peripheral positions and photophysicochemical properties of their zinc phthalocyanine derivatives. Dyes and Pigments. 2013;99(1):90-8.
  • [3] Wysocki M, Ziental D, Biyiklioglu Z, Jozkowiak M, Baş H, Dlugaszewska J, et al. Non-peripheral octasubstituted zinc (II) phthalocyanines bearing pyridinepropoxy substituents–Antibacterial, anticancer photodynamic and sonodynamic activity. Journal of Inorganic Biochemistry. 2025;262:112751.
  • [4] Khoza P, Antunes E, Nyokong T. Synthesis and photophysicochemical properties of zinc phthalocyanine derivatized with benzothiazole or carbazole photosensitizers. Polyhedron. 2013;61:119-25.
  • [5] Chen J, Chen Z, Zheng Y, Zhou S, Wang J, Chen N, et al. Substituted zinc phthalocyanine as an antimicrobial photosensitizer for periodontitis treatment. Journal of Porphyrins and Phthalocyanines. 2011;15(04):293-9.
  • [6] Sağlam Ö, Farajzadeh N, Yaşa Atmaca G, Erdoğmuş A, Koçak MB. Effect of position and connected atom on photophysical and photochemical properties of some fluorinated metallophthalocyanines. Photochemistry and Photobiology. 2021;97(2):270-7.
  • [7] Al-Raqa SY, Köksoy B, Durmuş M. A novel lutetium (III) acetate phthalocyanine directly substituted with N, N’-dimethylaminophenyl groups via CC bonds and its water-soluble derivative for photodynamic therapy. Tetrahedron letters. 2017;58(7):685-9.
  • [8] Kwiatkowski S, Knap B, Przystupski D, Saczko J, Kędzierska E, Knap-Czop K, et al. Photodynamic therapy–mechanisms, photosensitizers and combinations. Biomedicine & pharmacotherapy. 2018;106:1098-107.
  • [9] Atmaca GY, Erdoğmuş A. Synthesis of new water soluble silicon phthalocyanine substituted by linker sulfur atom and photophysicochemical studies for photodynamic therapy. Journal of Porphyrins and Phthalocyanines. 2019;23(11n12):1398-405.
  • [10] Yumita N, Umemura S-i. Sonodynamic antitumour effect of chloroaluminum phthalocyanine tetrasulfonate on murine solid tumour. Journal of pharmacy and pharmacology. 2004;56(1):85-90.
  • [11] Wan G-Y, Liu Y, Chen B-W, Liu Y-Y, Wang Y-S, Zhang N. Recent advances of sonodynamic therapy in cancer treatment. Cancer biology & medicine. 2016;13(3):325.
  • [12] Wang X, Zhong X, Bai L, Xu J, Gong F, Dong Z, et al. Ultrafine titanium monoxide (TiO1+ x) nanorods for enhanced sonodynamic therapy. Journal of the American Chemical Society. 2020;142(14):6527-37.
  • [13] Huang P, Qian X, Chen Y, Yu L, Lin H, Wang L, et al. Metalloporphyrin-encapsulated biodegradable nanosystems for highly efficient magnetic resonance imaging-guided sonodynamic cancer therapy. Journal of the American Chemical Society. 2017;139(3):1275-84.
  • [14] Nene LC, Sindelo A, Britton J, Nyokong T. Effect of ultrasonic frequency and power on the sonodynamic therapy activity of cationic Zn (II) phthalocyanines. Journal of Inorganic Biochemistry. 2021;217:111397.
  • [15] Borah BM, Cacaccio J, Durrani FA, Bshara W, Turowski SG, Spernyak JA, et al. Sonodynamic therapy in combination with photodynamic therapy shows enhanced long-term cure of brain tumor. Scientific Reports. 2020;10(1):21791.
  • [16] Canavese G, Ancona A, Racca L, Canta M, Dumontel B, Barbaresco F, et al. Nanoparticle-assisted ultrasound: A special focus on sonodynamic therapy against cancer. Chemical Engineering Journal. 2018;340:155-72.
  • [17] Can Karanlık C, Aguilar-Galindo F, Sobotta L, Guzel E, Erdogmus A. Combination of light and ultrasound: exploring sono–photochemical activities of phthalocyanine-based sensitizers. The Journal of Physical Chemistry C. 2023;127(19):9145-53.
  • [18] Atmaca GY, Aksel M, Bilgin MD, Erdoğmuş A. Comparison of sonodynamic, photodynamic and sonophotodynamic therapy activity of fluorinated pyridine substituted silicon phthalocyanines on PC3 prostate cancer cell line. Photodiagnosis and photodynamic therapy. 2023;42:103339.
  • [19] Alves F, Ayala ETP, Pratavieira S. Sonophotodynamic Inactivation: The power of light and ultrasound in the battle against microorganisms. Journal of Photochemistry and Photobiology. 2021;7:100039.
  • [20] Granados-Tavera K, Zambrano-Angulo M, Montenegro-Pohlhammer N, Atmaca GY, Sobotta L, Güzel E, et al. Synergistic effect of ultrasound and light to efficient singlet oxygen formation for photodynamic purposes. Dyes and Pigments. 2023;210:110986.
  • [21] Ogbodu RO, Nitzsche B, Ma A, Atilla D, Gürek AG, Höpfner M. Photodynamic therapy of hepatocellular carcinoma using tetra-triethyleneoxysulfonyl zinc phthalocyanine as photosensitizer. Journal of Photochemistry and Photobiology B: Biology. 2020;208:111915.
  • [22] Atmaca GY, Karanlık CC, Erdoğmuş A. Novel silicon phthalocyanines with improved singlet oxygen generation by Sono-photochemical applications. Journal of Photochemistry and Photobiology A: Chemistry. 2023;436:114365.
  • [23] Zheng Y, Ye J, Li Z, Chen H, Gao Y. Recent progress in sono-photodynamic cancer therapy: From developed new sensitizers to nanotechnology-based efficacy-enhancing strategies. Acta Pharmaceutica Sinica B. 2021;11(8):2197-219.
  • [24] Nene LC, Abrahamse H. Design consideration of phthalocyanines as sensitizers for enhanced sono-photodynamic combinatorial therapy of cancer. Acta Pharmaceutica Sinica B. 2024;14(3):1077-97.
  • [25] Ke M-R, Wang C, He Q, Que R, Wei Y, Zheng B-Y, et al. N-bridging tetra-substituted zinc (II) phthalocyanines with Q-band absorption up to 780 nm and eminent photosensitizing activities for photodynamic therapy. Dyes and Pigments. 2024;227:112169.
  • [26] Quartarolo AD, Lanzo I, Sicilia E, Russo N. Can phthalocyanines and their substituted α-para-(methoxy) phenyl derivatives act as photosensitizers in photodynamic therapy? A TD-DFT study. Physical Chemistry Chemical Physics. 2009;11(22):4586-92.
  • [27] Lo P-C, Rodríguez-Morgade MS, Pandey RK, Ng DK, Torres T, Dumoulin F. The unique features and promises of phthalocyanines as advanced photosensitisers for photodynamic therapy of cancer. Chemical Society Reviews. 2020;49(4):1041-56.
  • [28] Claessens CG, Hahn U, Torres T. Phthalocyanines: From outstanding electronic properties to emerging applications. The Chemical Record. 2008;8(2):75-97.
  • [29] Roguin LP, Chiarante N, Vior MCG, Marino J. Zinc (II) phthalocyanines as photosensitizers for antitumor photodynamic therapy. The international journal of biochemistry & cell biology. 2019;114:105575.
  • [30] Karanlık CC, Atmaca GY, Erdoğmuş A. Comparison of singlet oxygen production of ethyl vanillin substituted silicon phthalocyanine using sonophotodynamic and photodynamic methods. Journal of Molecular Structure. 2023;1274:134498.
  • [31] Burtsev I, Platonova YB, Volov A, Tomilova L. Synthesis, characterization and photochemical properties of novel octakis (p–fluorophenoxy) substituted phthalocyanine and its gallium and indium complexes. Polyhedron. 2020;188:114697.
  • [32] Calori IR, Tedesco AC. Aluminum chloride phthalocyanine in MCF-7: rationally accounting for state of aggregation of photosensitizers inside cells. Dyes and Pigments. 2020;173:107940.
  • [33] Oda K, Ogura S-i, Okura I. Preparation of a water-soluble fluorinated zinc phthalocyanine and its effect for photodynamic therapy. Journal of Photochemistry and Photobiology B: Biology. 2000;59(1-3):20-5.
  • [34] Yüzeroğlu M, Karaoğlan GK, Köse GG, Erdoğmuş A. Synthesis of new zinc phthalocyanines including schiff base and halogen; photophysical, photochemical, and fluorescence quenching studies. Journal of Molecular Structure. 2021;1238:130423.
  • [35] Roopa D, Shyamsunder K, Karunakar P, Rajabathar JR, Venkatesulu A, Karnan M, et al. Naphtho [2, 1-b] furan derived triazole-pyrimidines as highly potential InhA and Cytochrome c peroxidase inhibitors: synthesis, DFT calculations, drug-likeness profile, molecular docking and dynamic studies. Journal of Molecular Structure. 2023;1287:135685.
  • [36] Lehner V, Davies HM, Reiser O. Rh (II)-catalyzed cyclopropanation of furans and its application to the total synthesis of natural product derivatives. Organic letters. 2017;19(18):4722-5.
  • [37] Hithesh MC, Mohana KNS, Harsha YM, Sreelakshmi M, Madhusudhana AM, Kumar MCS. Effects of curing temperature and addition of functionalized graphene oxide on corrosion barrier performance of phenol furfural polymer-amino phenolic resin composite. Progress in Organic Coatings. 2024;188:108164.
  • [38] Güzel E, Şaki N, Akın M, Nebioğlu M, Şişman İ, Erdoğmuş A, et al. Zinc and chloroindium complexes of furan-2-ylmethoxy substituted phthalocyanines: Preparation and investigation of aggregation, singlet oxygen generation, antioxidant and antimicrobial properties. Synthetic Metals. 2018;245:127-34.
  • [39] Kahriman N, Ünver Y, Akçay HT, Gülmez AD, Durmuş M, Değirmencioğlu İ. Photophysical and photochemical study on novel axially chalcone substituted silicon (IV) phthalocyanines. Journal of Molecular Structure. 2020;1200:127132.
  • [40] Yarasir MN, Kandaz M, Güney O, Salih B. Synthesis and photophysical properties of metallophthalocyanines substituted with a benzofuran based fluoroprobe. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2012;93:379-83.
  • [41] Karanlık G, Ocak H, Eran BB. Imine based chiral liquid crystals: effect of varying the terminal substituent and orientation of ester linking unit. Journal of Molecular Liquids. 2019;275:567-77.
  • [42] Harmandar K, Saglam MF, Sengul IF, Ekineker G, Balcik-Ercin P, Göksel M, et al. Novel triazole containing zinc (II) phthalocyanine Schiff bases: Determination of photophysical and photochemical properties for photodynamic cancer therapy. Inorganica Chimica Acta. 2021;519:120286.
  • [43] Senge MO, Renner MW, Kallisch WW, Fajer J. Molecular structure of (5, 10, 15, 20-tetrabutyl-2, 3, 7, 8, 12, 13, 17, 18-octaethylporphyrinato) nickel (II)—correlation of nonplanarity with frontier orbital shifts. Journal of the Chemical Society, Dalton Transactions. 2000(3):381-5.
  • [44] Ünlü S, Elmalı FT, Atmaca GY, Erdoğmuş A. Synthesis of phenanthroline substituted five-nuclear phthalocyanine zinc complex and exploring of photochemical and sono-photochemical properties. Polyhedron. 2024;250:116817.
  • [45] Aydogdu S, Atmaca GY, Erdoğmuş A, Hatipoglu A. Synthesis of a new Zn-phthalocyanine, photophysical, photochemical, and sono-photochemical properties and DFT studies. Polyhedron. 2024;256:116989.
  • [46] Köse GG, Erdoğmuş A. Dual effect of light and ultrasound for efficient singlet oxygen generation with novel diaxial silicon phthalocyanine sensitizer. Photochemistry and Photobiology. 2024;100(1):52-66.
  • [47] Nyokong T. Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines. Coordination Chemistry Reviews. 2007;251(13-14):1707-22.
There are 47 citations in total.

Details

Primary Language English
Subjects Photochemistry, Organic Chemical Synthesis
Journal Section Articles
Authors

Gürkan Karanlık 0000-0003-2385-0166

Publication Date April 25, 2025
Submission Date December 10, 2024
Acceptance Date February 12, 2025
Published in Issue Year 2025 Volume: 29 Issue: 1

Cite

APA Karanlık, G. (2025). Novel Furan-Imine Substituted Zinc Phthalocyanine with Increased Singlet Oxygen Formation by Sono-Photochemical Method. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 29(1), 44-53. https://doi.org/10.19113/sdufenbed.1599212
AMA Karanlık G. Novel Furan-Imine Substituted Zinc Phthalocyanine with Increased Singlet Oxygen Formation by Sono-Photochemical Method. J. Nat. Appl. Sci. April 2025;29(1):44-53. doi:10.19113/sdufenbed.1599212
Chicago Karanlık, Gürkan. “Novel Furan-Imine Substituted Zinc Phthalocyanine With Increased Singlet Oxygen Formation by Sono-Photochemical Method”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 29, no. 1 (April 2025): 44-53. https://doi.org/10.19113/sdufenbed.1599212.
EndNote Karanlık G (April 1, 2025) Novel Furan-Imine Substituted Zinc Phthalocyanine with Increased Singlet Oxygen Formation by Sono-Photochemical Method. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 29 1 44–53.
IEEE G. Karanlık, “Novel Furan-Imine Substituted Zinc Phthalocyanine with Increased Singlet Oxygen Formation by Sono-Photochemical Method”, J. Nat. Appl. Sci., vol. 29, no. 1, pp. 44–53, 2025, doi: 10.19113/sdufenbed.1599212.
ISNAD Karanlık, Gürkan. “Novel Furan-Imine Substituted Zinc Phthalocyanine With Increased Singlet Oxygen Formation by Sono-Photochemical Method”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 29/1 (April2025), 44-53. https://doi.org/10.19113/sdufenbed.1599212.
JAMA Karanlık G. Novel Furan-Imine Substituted Zinc Phthalocyanine with Increased Singlet Oxygen Formation by Sono-Photochemical Method. J. Nat. Appl. Sci. 2025;29:44–53.
MLA Karanlık, Gürkan. “Novel Furan-Imine Substituted Zinc Phthalocyanine With Increased Singlet Oxygen Formation by Sono-Photochemical Method”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 29, no. 1, 2025, pp. 44-53, doi:10.19113/sdufenbed.1599212.
Vancouver Karanlık G. Novel Furan-Imine Substituted Zinc Phthalocyanine with Increased Singlet Oxygen Formation by Sono-Photochemical Method. J. Nat. Appl. Sci. 2025;29(1):44-53.

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