Photoinduced energy-transfer and electron-transfer processes in molecules of tetrakis((E)-2-(50-hexyl-2,20-bithiophen-5-yl)vinyl)benzene and perylenediimide

Mohamed E. El-Khouly, Dong Hoon Choi, Shunichi Fukuzumi

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Photoinduced energy- and electron-transfer processes of donor-σ-acceptor molecules composed of [1,2,4,5-tetrakis((E)-2-(50-hexyl- 2,20-bithiophen-5-yl)vinyl)benzene] (HPBT) with one, two and four entities of perylenediimide (PDI) forming HPBT-PDIn (n = 1, 2 and 4) have been examined in this article by utilizing steady-state absorption and emission, computational, electrochemical and time-resolved transient absorption studies. The HPBT-PDIn molecules are connected through long non-conjugated σ-bonds that may prevent the direct overlap of HPBT and PDI energy levels. Electrochemical studies suggest the exothermic photoinduced electron transfer processes when HPBT and PDI are selectively excited. Upon excitation the HPBT entity, the steady-state emission and femtosecond transient absorption measurements of HPBT-PDIn revealed an efficient energy transfer from the singlet excited HPBT to PDI with time constants on the order of ∼10 10 s-1. The energy donor-acceptor distance, r = ∼22 , is calculated from the experimental energy transfer rates using Förster theory and from the MO calculations using ab initio B3LYP/6-311G method. By selective excitation the PDI entity, the electron-transfer processes take place from HPBT to the singlet excited PDI with time constants on the order of ∼108 s-1. The slow rates of electron transfer and energy transfer processes indicated that these molecules tend to take conformations with relatively long distance between HPBT and PDI entities.

Original languageEnglish
Pages (from-to)17-25
Number of pages9
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume218
Issue number1
DOIs
Publication statusPublished - 2011 Feb 5

Fingerprint

Benzene
Energy transfer
electron transfer
energy transfer
benzene
Molecules
Electrons
time constant
molecules
Electron energy levels
excitation
Conformations
energy levels
perylenediimide
energy

Keywords

  • Electron transfer
  • Energy transfer
  • Oligothiophene
  • Perylenediimide

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

Cite this

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title = "Photoinduced energy-transfer and electron-transfer processes in molecules of tetrakis((E)-2-(50-hexyl-2,20-bithiophen-5-yl)vinyl)benzene and perylenediimide",
abstract = "Photoinduced energy- and electron-transfer processes of donor-σ-acceptor molecules composed of [1,2,4,5-tetrakis((E)-2-(50-hexyl- 2,20-bithiophen-5-yl)vinyl)benzene] (HPBT) with one, two and four entities of perylenediimide (PDI) forming HPBT-PDIn (n = 1, 2 and 4) have been examined in this article by utilizing steady-state absorption and emission, computational, electrochemical and time-resolved transient absorption studies. The HPBT-PDIn molecules are connected through long non-conjugated σ-bonds that may prevent the direct overlap of HPBT and PDI energy levels. Electrochemical studies suggest the exothermic photoinduced electron transfer processes when HPBT and PDI are selectively excited. Upon excitation the HPBT entity, the steady-state emission and femtosecond transient absorption measurements of HPBT-PDIn revealed an efficient energy transfer from the singlet excited HPBT to PDI with time constants on the order of ∼10 10 s-1. The energy donor-acceptor distance, r = ∼22 , is calculated from the experimental energy transfer rates using F{\"o}rster theory and from the MO calculations using ab initio B3LYP/6-311G method. By selective excitation the PDI entity, the electron-transfer processes take place from HPBT to the singlet excited PDI with time constants on the order of ∼108 s-1. The slow rates of electron transfer and energy transfer processes indicated that these molecules tend to take conformations with relatively long distance between HPBT and PDI entities.",
keywords = "Electron transfer, Energy transfer, Oligothiophene, Perylenediimide",
author = "El-Khouly, {Mohamed E.} and Choi, {Dong Hoon} and Shunichi Fukuzumi",
year = "2011",
month = "2",
day = "5",
doi = "10.1016/j.jphotochem.2010.11.018",
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journal = "Journal of Photochemistry and Photobiology A: Chemistry",
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TY - JOUR

T1 - Photoinduced energy-transfer and electron-transfer processes in molecules of tetrakis((E)-2-(50-hexyl-2,20-bithiophen-5-yl)vinyl)benzene and perylenediimide

AU - El-Khouly, Mohamed E.

AU - Choi, Dong Hoon

AU - Fukuzumi, Shunichi

PY - 2011/2/5

Y1 - 2011/2/5

N2 - Photoinduced energy- and electron-transfer processes of donor-σ-acceptor molecules composed of [1,2,4,5-tetrakis((E)-2-(50-hexyl- 2,20-bithiophen-5-yl)vinyl)benzene] (HPBT) with one, two and four entities of perylenediimide (PDI) forming HPBT-PDIn (n = 1, 2 and 4) have been examined in this article by utilizing steady-state absorption and emission, computational, electrochemical and time-resolved transient absorption studies. The HPBT-PDIn molecules are connected through long non-conjugated σ-bonds that may prevent the direct overlap of HPBT and PDI energy levels. Electrochemical studies suggest the exothermic photoinduced electron transfer processes when HPBT and PDI are selectively excited. Upon excitation the HPBT entity, the steady-state emission and femtosecond transient absorption measurements of HPBT-PDIn revealed an efficient energy transfer from the singlet excited HPBT to PDI with time constants on the order of ∼10 10 s-1. The energy donor-acceptor distance, r = ∼22 , is calculated from the experimental energy transfer rates using Förster theory and from the MO calculations using ab initio B3LYP/6-311G method. By selective excitation the PDI entity, the electron-transfer processes take place from HPBT to the singlet excited PDI with time constants on the order of ∼108 s-1. The slow rates of electron transfer and energy transfer processes indicated that these molecules tend to take conformations with relatively long distance between HPBT and PDI entities.

AB - Photoinduced energy- and electron-transfer processes of donor-σ-acceptor molecules composed of [1,2,4,5-tetrakis((E)-2-(50-hexyl- 2,20-bithiophen-5-yl)vinyl)benzene] (HPBT) with one, two and four entities of perylenediimide (PDI) forming HPBT-PDIn (n = 1, 2 and 4) have been examined in this article by utilizing steady-state absorption and emission, computational, electrochemical and time-resolved transient absorption studies. The HPBT-PDIn molecules are connected through long non-conjugated σ-bonds that may prevent the direct overlap of HPBT and PDI energy levels. Electrochemical studies suggest the exothermic photoinduced electron transfer processes when HPBT and PDI are selectively excited. Upon excitation the HPBT entity, the steady-state emission and femtosecond transient absorption measurements of HPBT-PDIn revealed an efficient energy transfer from the singlet excited HPBT to PDI with time constants on the order of ∼10 10 s-1. The energy donor-acceptor distance, r = ∼22 , is calculated from the experimental energy transfer rates using Förster theory and from the MO calculations using ab initio B3LYP/6-311G method. By selective excitation the PDI entity, the electron-transfer processes take place from HPBT to the singlet excited PDI with time constants on the order of ∼108 s-1. The slow rates of electron transfer and energy transfer processes indicated that these molecules tend to take conformations with relatively long distance between HPBT and PDI entities.

KW - Electron transfer

KW - Energy transfer

KW - Oligothiophene

KW - Perylenediimide

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U2 - 10.1016/j.jphotochem.2010.11.018

DO - 10.1016/j.jphotochem.2010.11.018

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EP - 25

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JF - Journal of Photochemistry and Photobiology A: Chemistry

SN - 1010-6030

IS - 1

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