Synthesis and photoinduced intramolecular processes of light-harvesting silicon phthalocyanine-naphthalenediimide-fullerene connected systems

Mohamed E. El-Khouly; Jung Hoon Kim; Kwang Yol Kay; Chan Soo Choi; Osamu Ito; Shunichi Fukuzumi

doi:10.1002/chem.200900165

Synthesis and photoinduced intramolecular processes of light-harvesting silicon phthalocyanine-naphthalenediimide-fullerene connected systems

Mohamed E. El-Khouly, Jung Hoon Kim, Kwang Yol Kay, Chan Soo Choi, Osamu Ito, Shunichi Fukuzumi

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

Photoinduced intramolecular processes of a newly synthesized pentad composed of silicon phthalocya- nine (SiPc) that is connected with two units of naphthalenediimide (NDI) and fullerene C₆₀ to form SiPc-(NDI) ₂- (C₆₀)₂ have been studied and the results are compared with the reference compounds, namely, the SiPc-(NDI)₂ triad and NDI-C₆₀ dyad. Upon photoexcita- tion, the main quenching pathway in polar solvents involved electron transfer via the singlet excited states of SiPc-(NDI)₂-(C₆₀)₂ and SiPc-(NDI)₂, but not NDI-C₆₀ for which the energy transfer is dominant. The occurrence of electron-transfer processes of SiPc- (NDI)₂-(C ₆₀)₂ and SiPc-(NDI)₂ were studied by time-resolved emission and transient absorption techniques and confirmed by redox measurements and molecular orbital calculations with ab initio B3LYP/3-21G(*) methods. Fast and efficient charge-separation processes via the singlet excited states of NDI and SiPc were monitored, followed by charge recombination to populate the C₆₀ and SiPc triplet states. The lifetimes of charge-separated states were estimated as 1000 and 250 ps for SiPc- (NDI)₂-(C₆₀)₂ and SiPc-(NDI)₂, respectively.

Original language	English
Pages (from-to)	5301-5310
Number of pages	10
Journal	Chemistry - A European Journal
Volume	15
Issue number	21
DOIs	https://doi.org/10.1002/chem.200900165
State	Published - 18 May 2009

Keywords

Electron transfer
Ful-lerenes
Laser chemistry
Naphtha- lenediimides
Photochemistry
Phthalocyanines

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title = "Synthesis and photoinduced intramolecular processes of light-harvesting silicon phthalocyanine-naphthalenediimide-fullerene connected systems",

abstract = "Photoinduced intramolecular processes of a newly synthesized pentad composed of silicon phthalocya- nine (SiPc) that is connected with two units of naphthalenediimide (NDI) and fullerene C60 to form SiPc-(NDI) 2- (C60)2 have been studied and the results are compared with the reference compounds, namely, the SiPc-(NDI)2 triad and NDI-C60 dyad. Upon photoexcita- tion, the main quenching pathway in polar solvents involved electron transfer via the singlet excited states of SiPc-(NDI)2-(C60)2 and SiPc-(NDI)2, but not NDI-C60 for which the energy transfer is dominant. The occurrence of electron-transfer processes of SiPc- (NDI)2-(C 60)2 and SiPc-(NDI)2 were studied by time-resolved emission and transient absorption techniques and confirmed by redox measurements and molecular orbital calculations with ab initio B3LYP/3-21G(*) methods. Fast and efficient charge-separation processes via the singlet excited states of NDI and SiPc were monitored, followed by charge recombination to populate the C60 and SiPc triplet states. The lifetimes of charge-separated states were estimated as 1000 and 250 ps for SiPc- (NDI)2-(C60)2 and SiPc-(NDI)2, respectively.",

keywords = "Electron transfer, Ful-lerenes, Laser chemistry, Naphtha- lenediimides, Photochemistry, Phthalocyanines",

author = "El-Khouly, \{Mohamed E.\} and Kim, \{Jung Hoon\} and Kay, \{Kwang Yol\} and Choi, \{Chan Soo\} and Osamu Ito and Shunichi Fukuzumi",

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AU - El-Khouly, Mohamed E.

AU - Kim, Jung Hoon

AU - Kay, Kwang Yol

AU - Choi, Chan Soo

AU - Ito, Osamu

AU - Fukuzumi, Shunichi

PY - 2009/5/18

Y1 - 2009/5/18

N2 - Photoinduced intramolecular processes of a newly synthesized pentad composed of silicon phthalocya- nine (SiPc) that is connected with two units of naphthalenediimide (NDI) and fullerene C60 to form SiPc-(NDI) 2- (C60)2 have been studied and the results are compared with the reference compounds, namely, the SiPc-(NDI)2 triad and NDI-C60 dyad. Upon photoexcita- tion, the main quenching pathway in polar solvents involved electron transfer via the singlet excited states of SiPc-(NDI)2-(C60)2 and SiPc-(NDI)2, but not NDI-C60 for which the energy transfer is dominant. The occurrence of electron-transfer processes of SiPc- (NDI)2-(C 60)2 and SiPc-(NDI)2 were studied by time-resolved emission and transient absorption techniques and confirmed by redox measurements and molecular orbital calculations with ab initio B3LYP/3-21G(*) methods. Fast and efficient charge-separation processes via the singlet excited states of NDI and SiPc were monitored, followed by charge recombination to populate the C60 and SiPc triplet states. The lifetimes of charge-separated states were estimated as 1000 and 250 ps for SiPc- (NDI)2-(C60)2 and SiPc-(NDI)2, respectively.

AB - Photoinduced intramolecular processes of a newly synthesized pentad composed of silicon phthalocya- nine (SiPc) that is connected with two units of naphthalenediimide (NDI) and fullerene C60 to form SiPc-(NDI) 2- (C60)2 have been studied and the results are compared with the reference compounds, namely, the SiPc-(NDI)2 triad and NDI-C60 dyad. Upon photoexcita- tion, the main quenching pathway in polar solvents involved electron transfer via the singlet excited states of SiPc-(NDI)2-(C60)2 and SiPc-(NDI)2, but not NDI-C60 for which the energy transfer is dominant. The occurrence of electron-transfer processes of SiPc- (NDI)2-(C 60)2 and SiPc-(NDI)2 were studied by time-resolved emission and transient absorption techniques and confirmed by redox measurements and molecular orbital calculations with ab initio B3LYP/3-21G(*) methods. Fast and efficient charge-separation processes via the singlet excited states of NDI and SiPc were monitored, followed by charge recombination to populate the C60 and SiPc triplet states. The lifetimes of charge-separated states were estimated as 1000 and 250 ps for SiPc- (NDI)2-(C60)2 and SiPc-(NDI)2, respectively.

KW - Electron transfer

KW - Ful-lerenes

KW - Laser chemistry

KW - Naphtha- lenediimides

KW - Photochemistry

KW - Phthalocyanines

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Synthesis and photoinduced intramolecular processes of light-harvesting silicon phthalocyanine-naphthalenediimide-fullerene connected systems

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Keywords

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