TY - JOUR
T1 - Photophysicochemical properties and TD-DFT calculations of a novel terminal alkyne substituted metal free phthalocyanine
AU - Yilmaz, Yusuf
AU - Mack, John
AU - Sönmez, Mehmet
AU - Nyokong, Tebello
N1 - Funding Information:
The authors wish to thank the Scientific and Technological Research Council of Turkey (TUBITAK) for financial support. This work was also supported by CSIR National Laser Centre, Rental Pool Programme, DST/NRF South African Research Chairs Initiative for Professor of Medicinal Chemistry and Nanotechnology and Rhodes University. The theoretical calculations were performed at the Centre for High Performance Computing in Cape Town, South Africa.
PY - 2014/3
Y1 - 2014/3
N2 - The synthesis of a novel free base tetrakis(prop-2-ynyloxy)phthalocyanine (2) is described, along with its characterization by IR, UV-visible absorption, and 1H NMR spectroscopy and mass spectrometry. The compound exhibited good solubility in a wide range of organic solvents and no significant aggregation was observed over a wide concentration range. The values for the singlet oxygen (ΦΔ), photodegradation, fluorescence (ΦF) and triplet state quantum yields and the fluorescence and triplet state lifetimes are reported. A relatively high ΦΔ value of 0.46 was obtained in DMSO. The ability to carry out "click" chemistry at the ligand periphery enhances the potential utility of 2 for use in bioconjugates in photodynamic therapy (PDT). A moderately high ΦF value of 0.18 is observed for emission in the therapeutic window in the near-IR region, which suggests that it may also be possible to determine the level of localization of 2 in tumor cells through bioimaging.
AB - The synthesis of a novel free base tetrakis(prop-2-ynyloxy)phthalocyanine (2) is described, along with its characterization by IR, UV-visible absorption, and 1H NMR spectroscopy and mass spectrometry. The compound exhibited good solubility in a wide range of organic solvents and no significant aggregation was observed over a wide concentration range. The values for the singlet oxygen (ΦΔ), photodegradation, fluorescence (ΦF) and triplet state quantum yields and the fluorescence and triplet state lifetimes are reported. A relatively high ΦΔ value of 0.46 was obtained in DMSO. The ability to carry out "click" chemistry at the ligand periphery enhances the potential utility of 2 for use in bioconjugates in photodynamic therapy (PDT). A moderately high ΦF value of 0.18 is observed for emission in the therapeutic window in the near-IR region, which suggests that it may also be possible to determine the level of localization of 2 in tumor cells through bioimaging.
KW - TD-DFT calculations
KW - phthalocyanine
KW - singlet oxygen quantum yields
UR - http://www.scopus.com/inward/record.url?scp=84900022218&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84900022218&partnerID=8YFLogxK
U2 - 10.1142/S1088424613501241
DO - 10.1142/S1088424613501241
M3 - Article
AN - SCOPUS:84900022218
VL - 18
SP - 251
EP - 258
JO - Journal of Porphyrins and Phthalocyanines
JF - Journal of Porphyrins and Phthalocyanines
SN - 1088-4246
IS - 3
ER -