TY - JOUR
T1 - A subphthalocyanine-pyrene dyad
T2 - Electron transfer and singlet oxygen generation
AU - El-Khouly, Mohamed E.
AU - El-Refaey, Ahmed
AU - Nam, Wonwoo
AU - Fukuzumi, Shunichi
AU - Göktuǧ, Özge
AU - Durmuş, Mahmut
N1 - Funding Information:
This work was supported financially by the Science and Technology Development Fund (STDF), Egypt (Grant Numbers 5537 and 12436 to MEK) and JSPS KAKENHI (16H02268 to S.F.), Japan.
Publisher Copyright:
© The Royal Society of Chemistry and Owner Societies 2017.
PY - 2017
Y1 - 2017
N2 - A light harvesting subphthalocyanine-pyrene dyad has been synthesized and characterized by linking pyrene (Py) with subphthalocyanine (SubPc) at its axial position with the B-O bond through the para position of the benzene group. Upon photoexcitation at the pyrene unit of the dyad, an efficient electron transfer from the singlet-excited state of Py to SubPc was observed. The electron transfer features were also observed by exciting the SubPc entity, but with slower rates (∼108 s-1). From the electrochemical measurements, the negative driving forces for charge separation via both the singlet states of Py and SubPc in the polar solvents indicate that the electron transfer is thermodynamically feasible. Interestingly, the examined compounds showed relatively high efficiency for producing the singlet oxygen (ΦΔ = ∼0.70). The collected data suggested the usefulness of the examined subphthalocyanine-pyrene dyad as a model of light harvesting system, as well as a sensitizer for photodynamic therapy.
AB - A light harvesting subphthalocyanine-pyrene dyad has been synthesized and characterized by linking pyrene (Py) with subphthalocyanine (SubPc) at its axial position with the B-O bond through the para position of the benzene group. Upon photoexcitation at the pyrene unit of the dyad, an efficient electron transfer from the singlet-excited state of Py to SubPc was observed. The electron transfer features were also observed by exciting the SubPc entity, but with slower rates (∼108 s-1). From the electrochemical measurements, the negative driving forces for charge separation via both the singlet states of Py and SubPc in the polar solvents indicate that the electron transfer is thermodynamically feasible. Interestingly, the examined compounds showed relatively high efficiency for producing the singlet oxygen (ΦΔ = ∼0.70). The collected data suggested the usefulness of the examined subphthalocyanine-pyrene dyad as a model of light harvesting system, as well as a sensitizer for photodynamic therapy.
UR - http://www.scopus.com/inward/record.url?scp=85031318457&partnerID=8YFLogxK
U2 - 10.1039/c7pp00166e
DO - 10.1039/c7pp00166e
M3 - Article
C2 - 28758668
AN - SCOPUS:85031318457
SN - 1474-905X
VL - 16
SP - 1512
EP - 1518
JO - Photochemical and Photobiological Sciences
JF - Photochemical and Photobiological Sciences
IS - 10
ER -