Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Novel Series of Peripherally Phthalocyanines (Zn, Pd and Cu): Spectroscopic Studies

Author(s): Asma Rahali*, Verónica Almeida-Marrero, Andrés de la Escosura, Tomás Torres and Raoudha Abderrahim*

Volume 20, Issue 7, 2023

Published on: 07 February, 2023

Page: [647 - 656] Pages: 10

DOI: 10.2174/1570178620666221227162819

Price: $65

Abstract

A new series of metallophthalocyanines (MPc) containing metals such as : Zn (II), Cu (II) and, Pd (II) were designed, synthesized, and characterized, using MS, IR and UV-Vis spectroscopy. A Suzuki cross-coupling reaction was investigated by using the Pd(dppf)Cl2 as a catalyst and cesium carbonate as a base to improve the yield of the precursor 2.6-di(pyridin-3-yl)- phenyl benzyl ether. The changes of metals, substituents, and positions increases the Q-band value from the monosubstituted to the octa-substituted macrocycles, and from Pd, to Cu to Zn complexes. All MPc showed quite similar IR spectra.

Keywords: Metallophthalocyanines, suzuki reaction, peripheral substituents, pyridine groups, metals, aggregation, UV-Vis.

Graphical Abstract
[1]
Gürol, I.; Durmuş, M.; Ahsen, V.; Nyokong, T. Dalton Trans., 2007, 43(34), 3782-3791.
[http://dx.doi.org/10.1039/b704345g] [PMID: 17712444]
[2]
Bonegardt, D.; Klyamer, D.; Krasnov, P.; Sukhikh, A. J. Fluor. Chem., 2021, 246, 1-8.
[3]
Rosenthal, I.; Krishna, C.M.; Riesz, P.; Ben-Hur, E. Radiat. Res., 1986, 107(1), 136-142.
[http://dx.doi.org/10.2307/3576857]
[4]
Collins, R.A.; Mohammed, K.A. J. Phys. (Paris), 1988, 21, 154-161.
[5]
Alberto, M.E.; De Simone, B.C.; Mazzone, G.; Sicilia, E.; Russo, N. Phys. Chem. Chem. Phys., 2015, 17(36), 23595-23601.
[http://dx.doi.org/10.1039/C5CP03833B]
[6]
Zhang, S.S.; Ren, X.; Tran, D.T.J.J. Green., 2012, 2, 63-69.
[7]
Konarev, D.V.; Kuzmin, A.V.; Faraonov, M.A.; Ishikawa, M.; Khasanov, S.S.; Nakano, Y.; Otsuka, A.; Yamochi, H.; Saito, G.; Lyubovskaya, R.N. Chemistry, 2014, 20(1), 1-16.
[http://dx.doi.org/10.1002/chem.201390210]
[8]
Yang, L.; Guo, L.; Chen, Q.; Sun, H.; Yan, H.; Zeng, Q.; Zhang, X.; Pan, X.; Dai, S. J. Mol. Graph. Model., 2012, 38, 82-89.
[http://dx.doi.org/10.1016/j.jmgm.2012.08.006]
[9]
Nnaji, N.; Sen, P.; Nyokong, T. J. Mol. Struct., 2021, 1242130806
[http://dx.doi.org/10.1016/j.molstruc.2021.130806]
[10]
Kobayashi, N.; Ogata, H.; Nonaka, N.; Luk’yanets, E.A. Chemistry, 2003, 9(20), 5123-5134.
[http://dx.doi.org/10.1002/chem.200304834]
[11]
Rollmann, L.D.; Iwamoto, R. J. Am. Chem. Soc., 1967, 9, 1455-1463.
[12]
Cranston, R.R.; Lessard, B.H.J. RSC, 2021, 11, 21716-21737.
[13]
Borker, P.; Salker, A.A. J. Chem. Eng. Technol., 2006, 13, 341-346.
[14]
Alberto, M.E.; de Simone, B.C.; Mazzone, G.; Sicilia, E.; Russo, N. J. Phys. Chem. Chem. Phys., 2015, 17, 23595-23601.
[15]
Abdel-Rahman, L.H.; Abdel-Mawgoud, A-M.M.; Shaaban, K.M.; Shehata, M.R.; Abdel-Hameed, M.; Abd-ElAleem, M.; El-Remaily, A.A.J. Appl. Organomet. Chem., 2022, 36, 6817-6820.
[16]
Ogunsipe, A.; Chen, J.Y.; Nyokong, T. New J. Chem., 2004, 28(7), 822-827.
[http://dx.doi.org/10.1039/B315319C]
[17]
Alzahrani, S.O.; Abu-Dief, A.M.; Alkhamis, K.; Alkhatib, F.; El-Dabea, T.; El-Remaily, M.A.E.A.A.A.; El-Metwaly, N.M. J. Mol. Liq., 2021, 332115844
[http://dx.doi.org/10.1016/j.molliq.2021.115844]
[18]
Abu-Dief, A.M.; El-Metwaly, N.M.; Alzahrani, S.O.; Alkhatib, F.; Abualnaja, M.M.; El-Dabea, T.; El-Remaily, M.A.E.A.A.A. J. Mol. Liq., 2021, 326115277
[http://dx.doi.org/10.1016/j.molliq.2021.115277]
[19]
Lukyanets, E.A.; Nemykin, V.N. J. Porphyr. Phthalocyanines, 2010, 14(1), 1-40.
[http://dx.doi.org/10.1142/S1088424610001799]
[20]
Halaskova, M.; Rahali, A.; Almeda-Marrero, V.; Machacek, M.; Kucera, R.; Jamoussi, B.; Torres, T.; Novakova, V.; de la Escosura, A.P.J. ACS Med. Chem. Lett., 2021, 12, 502-507.
[http://dx.doi.org/10.1021/acsmedchemlett.1c00045]
[21]
Anaya-Plaza, E.; Aljarilla, A.; Beaune, G.; Nonappa, J.; Timonen, J.V.I.; Escosura, A.; Torres, T.; Kostiainen, M.A. Adv. Mater., 2019, 31(39)1902582
[http://dx.doi.org/10.1002/adma.201902582]
[22]
Rahali, A.; Shaukat, A.; Almeida-Marrero, V.; Jamoussi, B.; de la Escosura, A.; Torres, T.; Kostiainen, M.A.; Anaya-Plaza, E. Bioconjug. Chem., 2021, 32(6), 1123-1129.
[http://dx.doi.org/10.1021/acs.bioconjchem.1c00176] [PMID: 34029458]
[23]
El-Remaily, M.A.E.A.A.A.; El-Dabea, T.; Alsawat, M.; Mahmoud, M.H.H.; Alfi, A.A.; El-Metwaly, N.; Abu-Dief, A.M. ACS Omega, 2021, 21071-21086.
[24]
El-Remaily, M.A.E.A.A.A.; Soliman, A.M.M.; Khalife, M.E.; El-Metwaly, N.M.; Alsoliemy, A.; El-Daea, T.; Abu-Dief, A.M.J. Appl. Organomet. Chem., 2021, 362, 1-18.
[25]
Ziminov, A.V.; Ramsh, S.M.; Terukoy, E.I.; Trapeznikova, I.N.V.V.; Shamanin, T.A. J. Semicond., 2006, 40, 1131-1136.
[http://dx.doi.org/10.1134/S1063782606100022]
[26]
Cook, G.L.; Church, F.M. J. Phys. Chem., 1957, 61(4), 458-462.
[http://dx.doi.org/10.1021/j150550a017]
[27]
Lyubimtsev, A.; Iqbal, Z.; Crucius, G.; Syrbu, S.; Taraymovich, E.S.; Ziegler, T.; Hanack, M. J. Porphyr. Phthalocyanines, 2011, 15(1), 39-46.
[http://dx.doi.org/10.1142/S1088424611002891]
[28]
Mack, J.; Stillman, M.J. Inorg. Chem., 2001, 40(4), 812-814.
[http://dx.doi.org/10.1021/ic0009829] [PMID: 11225128]

Rights & Permissions Print Export Cite as
© 2024 Bentham Science Publishers | Privacy Policy