Synthesis and electrochemical properties of copper(II), manganese(III) phthalocyanines bearing chalcone groups at peripheral or nonperipheral positions

In this study, new chalcone compound 1, new phthalonitrile derivatives 2 and 3, new copper(II), manganese(III) phthalocyanines bearing chalcone groups at peripheral or nonperipheral positions were synthesized. Electrochemistry of tetra-(4-{(2E)-3-[2-fluoro-4-(trifluoromethyl)phenyl]prop-2-enoyl}phenoxy) substituted Co(II)Pc and Mn(III)Pcs were studied with cyclic voltammetry (CV) to determine the redox properties of the phthalocyanines. According to the results, while the CuPcs 2a and 3a showed two Pc based reduction reactions and one Pc based oxidation reaction, MnPcs 2b and 3b gave two metal-based reduction reactions. All the redox processes are shifted toward positive potentials as a result of the increased electron-withdrawing ability of the trifluoromethyl substituents.

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  • Akyuz D, 2017, J ELECTROANAL CHEM, V804, P53, DOI 10.1016/j.jelechem.2017.09.044
  • Biyiklioglu Z, 2020, J MOL STRUCT, V1212, DOI 10.1016/j.molstruc.2020.128144
  • Biyiklioglu Z, 2019, INORG CHIM ACTA, V486, P345, DOI 10.1016/j.ica.2018.10.061
  • Cakir D, 2015, DALTON T, V44, P9646, DOI 10.1039/c5dt00747j
  • Canlica M, 2011, POLYHEDRON, V30, P508, DOI 10.1016/j.poly.2010.11.017
  • Demir F, 2014, J ELECTROCHEM SOC, V161, pG1, DOI 10.1149/2.002403jes
  • Farajzadeh N, 2020, POLYHEDRON, V177, DOI 10.1016/j.poly.2019.114264
  • Ghazal B, 2020, MOLECULES, V25, DOI 10.3390/molecules25071692
  • Gulmez AD, 2017, SENSOR ACTUAT B-CHEM, V241, P364, DOI 10.1016/j.snb.2016.10.073
  • Guo ZJ, 2019, RSC ADV, V9, P37518, DOI 10.1039/c9ra08065a
  • Kahriman N, 2020, BIOORG CHEM, V99, DOI 10.1016/j.bioorg.2020.103805
  • Kahriman N, 2020, J MOL STRUCT, V1200, DOI 10.1016/j.molstruc.2019.127132
  • Karaca H., 2018, J TURKISH CHEM SOC, V5, P701
  • Karaca H, 2018, J COORD CHEM, V71, P1606, DOI 10.1080/00958972.2018.1468027
  • Kong SW, 2019, J MOL LIQ, V288, DOI 10.1016/j.molliq.2019.111012
  • Kose GG, 2020, SYNTHETIC MET, V264, DOI 10.1016/j.synthmet.2020.116386
  • Li D, 2020, BIOORG MED CHEM LETT, V30, DOI 10.1016/j.bmcl.2020.127164
  • Lima LF, 2020, SENSOR ACTUAT B-CHEM, V310, P127893
  • Nas A, 2017, INORG CHIM ACTA, V466, P86, DOI 10.1016/j.ica.2017.05.050
  • Nas A, 2013, DYES PIGMENTS, V99, P90, DOI 10.1016/j.dyepig.2013.04.014
  • Praats R, 2020, ELECTROCHIM ACTA, V334, DOI 10.1016/j.electacta.2019.135575
  • Sahin S, 2020, SPECTROCHIM ACTA A, V227 .
  • Sarki G, 2019, J MOL STRUCT, V1196, P592, DOI 10.1016/j.molstruc.2019.05.123
  • Sekhosana KE, 2017, POLYHEDRON, V138, P154, DOI 10.1016/j.poly.2017.09.033
  • Senoglu S, 2020, SENSOR ACTUAT B-CHEM, V310, DOI 10.1016/j.snb.2020.127860
  • Sezer B, 2010, SYNTHETIC MET, V160, P2155, DOI 10.1016/j.synthmet.2010.08.002
  • Soganci T, 2018, ACS APPL MATER INTER, V10, P21654, DOI 10.1021/acsami.8b06206
  • Song C, 2020, MATER LETT, V270, DOI 10.1016/j.matlet.2020.127666
  • Tuncel S, 2012, ORG BIOMOL CHEM, V10, P1154, DOI 10.1039/c2ob06809e
  • Unver Y, 2019, J MOL STRUCT, V1178, P508, DOI 10.1016/j.molstruc.2018.10.072
  • Usta A, 2007, HELV CHIM ACTA, V90, P1482, DOI 10.1002/hlca.200790154
  • Xu JL, 2020, OPTIK, V200, DOI 10.1016/j.ijleo.2019.163413
  • Yabas E, 2018, POLYHEDRON, V153, P51, DOI 10.1016/j.poly.2018.06.044
  • Yalazan H, 2020, INORG CHEM COMMUN, V118, DOI 10.1016/j.inoche.2020.107998
  • Yalazan H, 2020, POLYHEDRON, V180, DOI 10.1016/j.poly.2020.114419
  • Yalazan H, 2020, J ORGANOMET CHEM, V912, DOI 10.1016/j.jorganchem.2020.121181
  • Yayli N, 2007, J PHOTOCH PHOTOBIO A, V188, P161, DOI 10.1016/j.jphotochem.2006.12.004
  • Yildiz B, 2019, SOL ENERGY, V191, P654, DOI 10.1016/j.solener.2019.09.043