Newly synthesized peripherally octa-substituted zinc phthalocyanines carrying halogen terminated phenoxy-phenoxy moiety: comparative photochemical and photophysical features

This study reports the 3 new phthalonitrile derivatives, namely 4, 5 Bis-[4-(4-bromophenoxy) phenoxy] phthalonitrile (1), 4,5 Bis-[4-(4-chlorophenoxy) phenoxy]phthalonitrile (2), and 4, 5 Bis[4-(4-fluorophenoxy) phenoxy] phthalonitrile (3). Their octasubstituted zinc phthalocyanines (4, 5, 6) are reported for the first time in this study. The resulting compounds were characterized by utilizing some spectroscopic methods, such as UV-Vis, 1HNMR, FT-IR spectroscopy, as well as mass spectraand elemental analysis. To show photosynthesizer’s potential, emission (FF), singlet oxygen (1O2), and photodegradation quantum yields (FΔ, Fd) of octaperipherally phthalocyanines (Pcs) were performed in the solutions, such as biocompatible solvent DMSO (dimethyl sulfoxide) as well as DMF (dimethylformamide) and THF (tetrahydrofuran). Solvent and octa-peripherally binding effect of the halogen (Br, Cl, F) terminated phenoxy-phenoxy groups on phthalocyanine rings for photophysicochemical properties (4, 5, and 6) were compared with the tetra-peripherally and tetra nonperipherally substituted derivatives. The new dyes (4 to 6) may be evaluated in photodynamic therapy (PDT) of cancer as photosensitizers due to efficient 1O2 from 0.55 to 0.75.

Keywords:

Photochemistry, photophysics, zinc phthalocyanine octa-substituted, halogen substitution,

PDF

___

Ahmetali E, 2019, J PORPHYR PHTHALOCYA, V23, P960, DOI 10.1142/S108842461950055X
BONNETT R, 1995, CHEM SOC REV, V24, P19, DOI 10.1039/cs9952400019
BRANNON JH, 1980, J AM CHEM SOC, V102, P62, DOI 10.1021/ja00521a011
Chen RR, 2009, J PHYS CHEM C, V113, P20689, DOI 10.1021/jp906408y
Dahlen MA, 1939, IND ENG CHEM, V31, P839, DOI 10.1021/ie50355a012
Durmus M, 2008, SPECTROCHIM ACTA A, V69, P1170, DOI 10.1016/j.saa.2007.06.029
Durmus M, 2009, DYES PIGMENTS, V82, P244, DOI 10.1016/j.dyepig.2009.01.008
Erdogmus A, 2014, J FLUORINE CHEM, V166, P127, DOI 10.1016/j.jfluchem.2014.08.005
Erdogmus A, 2009, POLYHEDRON, V28, P2855, DOI 10.1016/j.poly.2009.06.019
Fery-Forgues S, 1999, J CHEM EDUC, V76, P1260, DOI 10.1021/ed076p1260
Gonzalez- Rodriguez D, 2004, J AM CHEM SOC, V126, P6301, DOI 10.1021/ja039883v
Guzel E, 2017, J COORD CHEM, V70, P2659, DOI 10.1080/00958972.2017.1366471
HERRON N, 1986, J CHEM SOC CHEM COMM, P1521, DOI 10.1039/c39860001521
Keles T, 2019, INORG CHIM ACTA, V487, P201, DOI 10.1016/j.ica.2018.12.010
Kirbac E, 2020, J MOL STRUCT, V1202, DOI 10.1016/j.molstruc.2019.127392
Kirbac E, 2014, J ORGANOMET CHEM, V752, P115, DOI 10.1016/j.jorganchem.2013.12.005
Koca B, 2019, J PHYS CHEM C, V123, P24417, DOI 10.1021/acs.jpcc.9b07053
Korkmaz E, 2020, MONATSH CHEM, V151, P181, DOI 10.1007/s00706-019-02543-y
Kuznetsova NA, 2000, RUSS J GEN CHEM, V70, P133
Mack J, 2001, INORG CHEM, V40, P812, DOI 10.1021/ic0009829
Mackintosh HJ, 2008, J MATER CHEM, V18, P573, DOI 10.1039/b715660j
Mahapatra NN, 2018, TEXTILE DYEING .
Michael H, 2002, CHEM REC, V2, P129, DOI [10.1002/tcr.10024, DOI 10.1002/TCR.10024]
Nyokong T, 2007, COORDIN CHEM REV, V251, P1707, DOI 10.1016/j.ccr.2006.11.011
Ogunsipe A, 2005, J PHOTOCH PHOTOBIO A, V173, P211, DOI 10.1016/j.jphotochem.2005.03.001
Ogunsipe A, 2004, NEW J CHEM, V28, P822, DOI 10.1039/b315319c
Ogunsipe A, 2003, J MOL STRUCT, V650, P131, DOI 10.1016/S0022-2860(03)00155-8
Peumans P, 2001, APPL PHYS LETT, V79, P126, DOI 10.1063/1.1384001
Saka ET, 2011, J ORGANOMET CHEM, V696, P913, DOI 10.1016/j.jorganchem.2010.10.024
Schumann S, 2011, J PHYS CHEM C, V115, P4916, DOI 10.1021/jp109544m
Seotsanyana-Mokhosi I, 2001, J PHOTOCH PHOTOBIO A, V140, P215, DOI 10.1016/S1010-6030(01)00427-0
Sezer B, 2010, SYNTHETIC MET, V160, P2155, DOI 10.1016/j.synthmet.2010.08.002
SIMON J, 1989, PURE APPL CHEM, V61, P1625, DOI 10.1351/pac198961091625
SPIKES JD, 1986, PHOTOCHEM PHOTOBIOL, V43, P691, DOI 10.1111/j.1751-1097.1986.tb05648.x
Spiller W, 1998, J PORPHYR PHTHALOCYA, V2, P145, DOI 10.1002/(SICI)1099-1409(199803/04)2:2<145::AID-JPP60>3.0.CO;2-2
Ugur AL, 2010, POLYHEDRON, V29, P3310, DOI 10.1016/j.poly.2010.09.008
Vogel M, 2006, APPL PHYS LETT, V89, DOI 10.1063/1.2362624