TY - JOUR
T1 - Tetra and octa(2,6-di-iso-propylphenoxy)-substituted phthalocyanines:
AU - Tuhl, Ahmad
AU - Chidawanayika, Wadzanai
AU - Ibrahim, Hamada Mohamed
AU - Al-Awadi, Nouria
AU - Litwinski, Christian
AU - Nyokong, Tebello
AU - Behbehani, Haider
AU - Manaa, Hacene
AU - Makhseed, Saad
N1 - Funding Information:
AT wishes to thank the College of Graduate Studies, Kuwait University for a Ph.D. candidacy. The financial support of ANALAB and SAF grants (Nos. GS 01/01, GS 01/05 and GS 03/01), Kuwait University, and the support by the Department of Science and Technology (DST) and National Research Foundation (NRF), South Africa through DST/NRF Chairs Initiative for Professor of Medicinal Chemistry and Nanotechnology and Rhodes University are gratefully acknowledged. WC thanks Rhodes University for funding.
PY - 2012/1
Y1 - 2012/1
N2 - This work reports on the synthesis of novel metal free, zinc, aluminum, gallium and indium tetra and octa (2,6-di-iso-propylphenoxy)-substituted phthalocyanine derivatives. UV-visible and 1H NMR analyses confirm that a non-planar conformation, adapted by the phenoxy substituents due to steric interaction in both derivative series, perfectly discourage cofacial aggregation. Fluorescence quantum yields vary as a function of the number of substituents on the ring periphery, while the fluorescence lifetimes display no distinct trend. Triplet quantum yields are significantly larger for the tetra 2,6-di-iso-propylphenoxy- substituted derivatives relative to their corresponding octa-substituted species. However there was no overall trend in the triplet lifetime values. For almost all of the phthalocyanine derivatives, singlet oxygen was produced with relatively good quantum yields. This study explores the possibility of fine-tuning their physicochemical properties by simple structural modification.
AB - This work reports on the synthesis of novel metal free, zinc, aluminum, gallium and indium tetra and octa (2,6-di-iso-propylphenoxy)-substituted phthalocyanine derivatives. UV-visible and 1H NMR analyses confirm that a non-planar conformation, adapted by the phenoxy substituents due to steric interaction in both derivative series, perfectly discourage cofacial aggregation. Fluorescence quantum yields vary as a function of the number of substituents on the ring periphery, while the fluorescence lifetimes display no distinct trend. Triplet quantum yields are significantly larger for the tetra 2,6-di-iso-propylphenoxy- substituted derivatives relative to their corresponding octa-substituted species. However there was no overall trend in the triplet lifetime values. For almost all of the phthalocyanine derivatives, singlet oxygen was produced with relatively good quantum yields. This study explores the possibility of fine-tuning their physicochemical properties by simple structural modification.
KW - di-iso-propylphenoxy
KW - photochemistry
KW - photophysics
KW - phthalocyanine
UR - https://www.scopus.com/pages/publications/84860460817
U2 - 10.1142/S1088424612004495
DO - 10.1142/S1088424612004495
M3 - Article
AN - SCOPUS:84860460817
SN - 1088-4246
VL - 16
SP - 163
EP - 174
JO - Journal of Porphyrins and Phthalocyanines
JF - Journal of Porphyrins and Phthalocyanines
IS - 1
ER -