Araştırma Makalesi
BibTex RIS Kaynak Göster

Yıl 2026, Cilt: 16 Sayı: 1, 243 - 256, 01.03.2026
https://doi.org/10.21597/jist.1710937
https://izlik.org/JA98NZ53FS

Öz

Kaynakça

  • Aktas, S., Unal, F., Kurt, M. S., Koç, M. M., Arslan, T., Aslan, N., & Coşkun, B. (2023). Investigation of fundamental electrical and optoelectronic properties of an organic-and carbon-based MnPc/GC photodiode with high photosensitivity. Physica Scripta, 98(9), 095504.
  • Biyiklioglu, Z., Çekirge, E., Baş, H., Özbek, N., Ocak, Ü., & Ocak, M. (2024). New fluorescent manganese (III) phthalocyanines bearing non-peripherally octa-(3-pyridin-3-ylpropoxy) and (4-pyridin-3-ylpropoxy) for the sensitive determination of Pd2+ in real water samples. Inorganic Chemistry Communications, 159, 111824.
  • Darwish, A. A. A., Helali, S., Qashou, S. I., Yahia, I. S., & El-Zaidia, E. F. M. (2021). Studying the surface morphology, linear and nonlinear optical properties of manganese (III) phthalocyanine chloride/FTO films. Physica B: Condensed Matter, 622, 413355.
  • Ganesan, V., Madrid, E., Malpass-Evans, R., Carta, M., McKeown, N. B., & Marken, F. (2019). Biphasic voltammetry and spectroelectrochemistry in polymer of intrinsic microporosity—4-(3-phenylpropyl)-pyridine organogel/aqueous electrolyte systems: reactivity of MnPc versus MnTPP. Electrocatalysis, 10, 295-304.
  • Hu, Q., Rezaee, E., Li, M., Chen, Q., Cao, Y., Mayukh, M., ... & Xu, Z. X. (2019). Molecular design strategy in developing titanyl phthalocyanines as dopant-free hole-transporting materials for perovskite solar cells: Peripheral or nonperipheral substituents?. ACS applied materials & interfaces, 11(40), 36535-36543.
  • Kobak, R. Z. U., Arı, M. U., Tekin, A., & Gül, A. (2015). Aggregation behavior in unsymmetrically substituted metal-free phthalocyanines. Chemical Physics, 448, 91-97.
  • Luna Zempoalteca, A., Hernández de la Luz, J. Á. D., Luna Flores, A., Luna López, J. A., & Benítez Lara, A. (2023). MnPc Films Deposited by Ultrasonic Spray Pyrolysis at Low Temperatures: Optical, Morphological and Structural Properties. Materials, 16(12), 4357.
  • Özçeşmeci, M., Baş, S. S., Akkurt, B., Bolkent, Ş., & Hamuryudan, E. (2020). Synthesis, characterization and staining performance of peripherally and non-peripherally substituted metallo-phthalocyanines bearing 1, 3-bis-(trimethylamino)-2-propoxy groups. New Journal of Chemistry, 44(19), 7786-7794.
  • Özçeşmeci, M., Özkan, E., & Hamuryudan, E. (2013). Synthesis, characterization, and aggregation properties of functionalized polyfluorinated metallo-phthalocyanines. Journal of Porphyrins and Phthalocyanines, 17(10), 972-979.
  • Tirink, S., Nuhoğlu, A. ve Kul, S. (2020). Characterization of pistachio processing industry wastewater and investigation of chemical pretreatment. Environmental Research and Technology, 3(4), 209-216.
  • Parimala, S., Kandaswamy, M., Nissa, M. N., & Velmurugan, D. (2003). Structural, magnetic and electrochemical studies of a new series of macrocyclic mononuclear and binuclear Manganese (III) and unusually stable Manganese (II) complexes. Journal of Coordination Chemistry, 56(4), 261-274.
  • Samsunlu, T., Akkoç, B., Özçeşmeci, M., Akın, M., Şaki, N., & Hamuryudan, E. (2023). Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions. ChemistrySelect, 8(18), e202205001.
  • Sarkı, G., Yalazan, H., & Kantekin, H. (2020). Synthesis and aggregation properties of 2, 9, 16, 23–tetrakis (chloro)-3, 10, 17, 24–tetrakis [2-(4-allyl-2methoxyphenoxy) ethoxy] phthalocyaninato cobalt (II), manganese (III), zinc (II). Turkish Journal of Analytical Chemistry, 2(2), 75-80.
  • Soganci, T., Baygu, Y., Kabay, N., Gok, Y., & Ak, M. (2018). Comparative investigation of peripheral and nonperipheral zinc phthalocyanine-based polycarbazoles in terms of optical, electrical, and sensing properties. ACS Applied Materials & Interfaces, 10(25), 21654-21665.
  • Srivastava, A. K., Ghosh, S., & Pal, S. (2019). A one-dimensional polymeric mixed-valent Mn (II) Mn (III) complex with a macrocyclic compartmental ligand: Structure, properties and catecholase like activity. Polyhedron, 172, 112-119.
  • Urbain, E., Ibrahim, F., Studniarek, M., Nyakam, F. N., Joly, L., Arabski, J., ... & Weber, W. (2018). Cu metal/Mn phthalocyanine organic spinterfaces atop Co with high spin polarization at room temperature. Advanced Functional Materials, 28(29), 1707123.
  • Yang, K., Liu, L., Zhang, L., Xiao, W., Fei, X., Chen, H., ... & Gao, H. J. (2014). Reversible achiral-to-chiral switching of single Mn–phthalocyanine molecules by thermal hydrogenation and inelastic electron tunneling dehydrogenation. ACS nano, 8(3), 2246-2251.
  • Yuksel, F., Atilla, D., & Ahsen, V. (2007). Synthesis and characterization of liquid crystalline unsymmetrically substituted phthalocyanines. Polyhedron, 26(15), 4551-4556. Vertsimakha, Y., Mamykin, S., & Lutsyk, P. (2012). Substitution of phthalocyanines affecting the properties of their films and heterostructures. Chemical Physics, 404, 16-21.
  • Zhong, J. Q., Wang, Z., Zhang, J. L., Wright, C. A., Yuan, K., Gu, C., ... & Chen, W. (2015). Reversible tuning of interfacial and intramolecular charge transfer in individual MnPc molecules. Nano Letters, 15(12), 8091-8098.

Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability

Yıl 2026, Cilt: 16 Sayı: 1, 243 - 256, 01.03.2026
https://doi.org/10.21597/jist.1710937
https://izlik.org/JA98NZ53FS

Öz

Two Mn(III) phthalocyanine complexes bearing sulfonylphenoxy substituents in peripheral and nonperipheral positions were synthesized and comparatively analyzed. Their structural, optical, and thermal behaviors were examined using FT-IR, UV-Vis, MALDI-TOF-MS, TGA/DTA, and XRD techniques. The substitution position was found to significantly affect aggregation, solubility, crystallinity, and decomposition profile. The nonperipheral complex exhibited reduced aggregation, sharper absorption features, and superior thermal resistance, attributed to better electron delocalization and steric protection. MALDI-TOF-MS confirmed its more stable ionization with fewer fragment signals. In contrast, the peripheral analogue showed higher aggregation and earlier thermal degradation. XRD patterns also revealed that nonperipheral substitution led to more ordered packing and sharper diffraction peaks. UV-Vis spectra showed bathochromic shifts and monomeric behavior for the nonperipheral compound, while the peripheral one presented broader bands and signs of H-type aggregation. These results clearly demonstrate that minor changes in substitution geometry play a key role in modulating the physicochemical properties of Mn(III) phthalocyanines, offering design advantages for their use in optoelectronic, sensing, and high-temperature applications.

Kaynakça

  • Aktas, S., Unal, F., Kurt, M. S., Koç, M. M., Arslan, T., Aslan, N., & Coşkun, B. (2023). Investigation of fundamental electrical and optoelectronic properties of an organic-and carbon-based MnPc/GC photodiode with high photosensitivity. Physica Scripta, 98(9), 095504.
  • Biyiklioglu, Z., Çekirge, E., Baş, H., Özbek, N., Ocak, Ü., & Ocak, M. (2024). New fluorescent manganese (III) phthalocyanines bearing non-peripherally octa-(3-pyridin-3-ylpropoxy) and (4-pyridin-3-ylpropoxy) for the sensitive determination of Pd2+ in real water samples. Inorganic Chemistry Communications, 159, 111824.
  • Darwish, A. A. A., Helali, S., Qashou, S. I., Yahia, I. S., & El-Zaidia, E. F. M. (2021). Studying the surface morphology, linear and nonlinear optical properties of manganese (III) phthalocyanine chloride/FTO films. Physica B: Condensed Matter, 622, 413355.
  • Ganesan, V., Madrid, E., Malpass-Evans, R., Carta, M., McKeown, N. B., & Marken, F. (2019). Biphasic voltammetry and spectroelectrochemistry in polymer of intrinsic microporosity—4-(3-phenylpropyl)-pyridine organogel/aqueous electrolyte systems: reactivity of MnPc versus MnTPP. Electrocatalysis, 10, 295-304.
  • Hu, Q., Rezaee, E., Li, M., Chen, Q., Cao, Y., Mayukh, M., ... & Xu, Z. X. (2019). Molecular design strategy in developing titanyl phthalocyanines as dopant-free hole-transporting materials for perovskite solar cells: Peripheral or nonperipheral substituents?. ACS applied materials & interfaces, 11(40), 36535-36543.
  • Kobak, R. Z. U., Arı, M. U., Tekin, A., & Gül, A. (2015). Aggregation behavior in unsymmetrically substituted metal-free phthalocyanines. Chemical Physics, 448, 91-97.
  • Luna Zempoalteca, A., Hernández de la Luz, J. Á. D., Luna Flores, A., Luna López, J. A., & Benítez Lara, A. (2023). MnPc Films Deposited by Ultrasonic Spray Pyrolysis at Low Temperatures: Optical, Morphological and Structural Properties. Materials, 16(12), 4357.
  • Özçeşmeci, M., Baş, S. S., Akkurt, B., Bolkent, Ş., & Hamuryudan, E. (2020). Synthesis, characterization and staining performance of peripherally and non-peripherally substituted metallo-phthalocyanines bearing 1, 3-bis-(trimethylamino)-2-propoxy groups. New Journal of Chemistry, 44(19), 7786-7794.
  • Özçeşmeci, M., Özkan, E., & Hamuryudan, E. (2013). Synthesis, characterization, and aggregation properties of functionalized polyfluorinated metallo-phthalocyanines. Journal of Porphyrins and Phthalocyanines, 17(10), 972-979.
  • Tirink, S., Nuhoğlu, A. ve Kul, S. (2020). Characterization of pistachio processing industry wastewater and investigation of chemical pretreatment. Environmental Research and Technology, 3(4), 209-216.
  • Parimala, S., Kandaswamy, M., Nissa, M. N., & Velmurugan, D. (2003). Structural, magnetic and electrochemical studies of a new series of macrocyclic mononuclear and binuclear Manganese (III) and unusually stable Manganese (II) complexes. Journal of Coordination Chemistry, 56(4), 261-274.
  • Samsunlu, T., Akkoç, B., Özçeşmeci, M., Akın, M., Şaki, N., & Hamuryudan, E. (2023). Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions. ChemistrySelect, 8(18), e202205001.
  • Sarkı, G., Yalazan, H., & Kantekin, H. (2020). Synthesis and aggregation properties of 2, 9, 16, 23–tetrakis (chloro)-3, 10, 17, 24–tetrakis [2-(4-allyl-2methoxyphenoxy) ethoxy] phthalocyaninato cobalt (II), manganese (III), zinc (II). Turkish Journal of Analytical Chemistry, 2(2), 75-80.
  • Soganci, T., Baygu, Y., Kabay, N., Gok, Y., & Ak, M. (2018). Comparative investigation of peripheral and nonperipheral zinc phthalocyanine-based polycarbazoles in terms of optical, electrical, and sensing properties. ACS Applied Materials & Interfaces, 10(25), 21654-21665.
  • Srivastava, A. K., Ghosh, S., & Pal, S. (2019). A one-dimensional polymeric mixed-valent Mn (II) Mn (III) complex with a macrocyclic compartmental ligand: Structure, properties and catecholase like activity. Polyhedron, 172, 112-119.
  • Urbain, E., Ibrahim, F., Studniarek, M., Nyakam, F. N., Joly, L., Arabski, J., ... & Weber, W. (2018). Cu metal/Mn phthalocyanine organic spinterfaces atop Co with high spin polarization at room temperature. Advanced Functional Materials, 28(29), 1707123.
  • Yang, K., Liu, L., Zhang, L., Xiao, W., Fei, X., Chen, H., ... & Gao, H. J. (2014). Reversible achiral-to-chiral switching of single Mn–phthalocyanine molecules by thermal hydrogenation and inelastic electron tunneling dehydrogenation. ACS nano, 8(3), 2246-2251.
  • Yuksel, F., Atilla, D., & Ahsen, V. (2007). Synthesis and characterization of liquid crystalline unsymmetrically substituted phthalocyanines. Polyhedron, 26(15), 4551-4556. Vertsimakha, Y., Mamykin, S., & Lutsyk, P. (2012). Substitution of phthalocyanines affecting the properties of their films and heterostructures. Chemical Physics, 404, 16-21.
  • Zhong, J. Q., Wang, Z., Zhang, J. L., Wright, C. A., Yuan, K., Gu, C., ... & Chen, W. (2015). Reversible tuning of interfacial and intramolecular charge transfer in individual MnPc molecules. Nano Letters, 15(12), 8091-8098.
Toplam 19 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Organik Kimyasal Sentez, Organik Kimya (Diğer)
Bölüm Araştırma Makalesi
Yazarlar

Beyza Cabir 0000-0003-4735-4511

Gönderilme Tarihi 2 Haziran 2025
Kabul Tarihi 20 Temmuz 2025
Yayımlanma Tarihi 1 Mart 2026
DOI https://doi.org/10.21597/jist.1710937
IZ https://izlik.org/JA98NZ53FS
Yayımlandığı Sayı Yıl 2026 Cilt: 16 Sayı: 1

Kaynak Göster

APA Cabir, B. (2026). Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability. Journal of the Institute of Science and Technology, 16(1), 243-256. https://doi.org/10.21597/jist.1710937
AMA 1.Cabir B. Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability. Iğdır Üniv. Fen Bil Enst. Der. 2026;16(1):243-256. doi:10.21597/jist.1710937
Chicago Cabir, Beyza. 2026. “Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability”. Journal of the Institute of Science and Technology 16 (1): 243-56. https://doi.org/10.21597/jist.1710937.
EndNote Cabir B (01 Mart 2026) Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability. Journal of the Institute of Science and Technology 16 1 243–256.
IEEE [1]B. Cabir, “Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability”, Iğdır Üniv. Fen Bil Enst. Der., c. 16, sy 1, ss. 243–256, Mar. 2026, doi: 10.21597/jist.1710937.
ISNAD Cabir, Beyza. “Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability”. Journal of the Institute of Science and Technology 16/1 (01 Mart 2026): 243-256. https://doi.org/10.21597/jist.1710937.
JAMA 1.Cabir B. Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability. Iğdır Üniv. Fen Bil Enst. Der. 2026;16:243–256.
MLA Cabir, Beyza. “Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability”. Journal of the Institute of Science and Technology, c. 16, sy 1, Mart 2026, ss. 243-56, doi:10.21597/jist.1710937.
Vancouver 1.Beyza Cabir. Peripheral vs Nonperipheral Sulfonyl-Modified Mn(III) Phthalocyanines: Comparative Characterization of Aggregation Behavior and Thermal Stability. Iğdır Üniv. Fen Bil Enst. Der. 01 Mart 2026;16(1):243-56. doi:10.21597/jist.1710937