Photoinduced electron transfer through hydrogen bonds in a rod-like donor-acceptor molecule: A time-resolved EPR study

Manuela Jakob, Alexander Berg, Eli Stavitski, Erin T. Chernick, Emily A Weiss, Michael R Wasielewski, Haim Levanon

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Light-driven multi-step intramolecular electron transfer in a rod-like triad, in which two of the three redox components are linked by three hydrogen bonds, was studied by time-resolved electron paramagnetic resonance (TREPR) and optical spectroscopies. One part of the molecule consists of a p-methoxyaniline primary electron donor (MeOAn) covalently linked to a 4-aminonaphthalene-1, 8-dicarboximide (6ANI) chromophoric electron acceptor (MeOAn-6ANI). The unsubstituted dicarboximide of 6ANI serves as one half of a hydrogen bonding receptor pair. The other half of the receptor pair consists of a melamine linked to a naphthalene-1,8:4,5-bis(dicarboximide) (NI) secondary electron acceptor (MEL-NI). TREPR spectroscopy is used to probe the electronic interaction between the radicals within the photogenerated, spin-correlated radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}-. The results are compared to those obtained in earlier studies in which MeOAn-6ANI is covalently linked to NI through a 2,5-dimethylphenyl group (MeOAn-6ANI-Ph-NI). We show that the electronic coupling between the oxidized donor and reduced acceptor in the hydrogen-bonded radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}- is very similar to that of MeOAn{radical dot}+-6ANI-Ph-NI{radical dot}-.

Original languageEnglish
Pages (from-to)63-71
Number of pages9
JournalChemical Physics
Volume324
Issue number1 SPEC. ISS.
DOIs
Publication statusPublished - May 9 2006

Fingerprint

Paramagnetic resonance
Hydrogen bonds
electron transfer
rods
hydrogen bonds
Molecules
Electrons
molecules
1-Naphthylamine
Ions
Hydrogen
electron paramagnetic resonance
Spectroscopy
melamine
electrons
hydrogen
electronics
naphthalene
spectroscopy
ions

Keywords

  • Electron paramagnetic resonance
  • Electron transfer
  • Photochemistry
  • Radical pairs

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

Photoinduced electron transfer through hydrogen bonds in a rod-like donor-acceptor molecule : A time-resolved EPR study. / Jakob, Manuela; Berg, Alexander; Stavitski, Eli; Chernick, Erin T.; Weiss, Emily A; Wasielewski, Michael R; Levanon, Haim.

In: Chemical Physics, Vol. 324, No. 1 SPEC. ISS., 09.05.2006, p. 63-71.

Research output: Contribution to journalArticle

Jakob, Manuela ; Berg, Alexander ; Stavitski, Eli ; Chernick, Erin T. ; Weiss, Emily A ; Wasielewski, Michael R ; Levanon, Haim. / Photoinduced electron transfer through hydrogen bonds in a rod-like donor-acceptor molecule : A time-resolved EPR study. In: Chemical Physics. 2006 ; Vol. 324, No. 1 SPEC. ISS. pp. 63-71.
@article{c28f54c7a3f243eca415096d8f217a90,
title = "Photoinduced electron transfer through hydrogen bonds in a rod-like donor-acceptor molecule: A time-resolved EPR study",
abstract = "Light-driven multi-step intramolecular electron transfer in a rod-like triad, in which two of the three redox components are linked by three hydrogen bonds, was studied by time-resolved electron paramagnetic resonance (TREPR) and optical spectroscopies. One part of the molecule consists of a p-methoxyaniline primary electron donor (MeOAn) covalently linked to a 4-aminonaphthalene-1, 8-dicarboximide (6ANI) chromophoric electron acceptor (MeOAn-6ANI). The unsubstituted dicarboximide of 6ANI serves as one half of a hydrogen bonding receptor pair. The other half of the receptor pair consists of a melamine linked to a naphthalene-1,8:4,5-bis(dicarboximide) (NI) secondary electron acceptor (MEL-NI). TREPR spectroscopy is used to probe the electronic interaction between the radicals within the photogenerated, spin-correlated radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}-. The results are compared to those obtained in earlier studies in which MeOAn-6ANI is covalently linked to NI through a 2,5-dimethylphenyl group (MeOAn-6ANI-Ph-NI). We show that the electronic coupling between the oxidized donor and reduced acceptor in the hydrogen-bonded radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}- is very similar to that of MeOAn{radical dot}+-6ANI-Ph-NI{radical dot}-.",
keywords = "Electron paramagnetic resonance, Electron transfer, Photochemistry, Radical pairs",
author = "Manuela Jakob and Alexander Berg and Eli Stavitski and Chernick, {Erin T.} and Weiss, {Emily A} and Wasielewski, {Michael R} and Haim Levanon",
year = "2006",
month = "5",
day = "9",
doi = "10.1016/j.chemphys.2005.11.044",
language = "English",
volume = "324",
pages = "63--71",
journal = "Chemical Physics",
issn = "0301-0104",
publisher = "Elsevier",
number = "1 SPEC. ISS.",

}

TY - JOUR

T1 - Photoinduced electron transfer through hydrogen bonds in a rod-like donor-acceptor molecule

T2 - A time-resolved EPR study

AU - Jakob, Manuela

AU - Berg, Alexander

AU - Stavitski, Eli

AU - Chernick, Erin T.

AU - Weiss, Emily A

AU - Wasielewski, Michael R

AU - Levanon, Haim

PY - 2006/5/9

Y1 - 2006/5/9

N2 - Light-driven multi-step intramolecular electron transfer in a rod-like triad, in which two of the three redox components are linked by three hydrogen bonds, was studied by time-resolved electron paramagnetic resonance (TREPR) and optical spectroscopies. One part of the molecule consists of a p-methoxyaniline primary electron donor (MeOAn) covalently linked to a 4-aminonaphthalene-1, 8-dicarboximide (6ANI) chromophoric electron acceptor (MeOAn-6ANI). The unsubstituted dicarboximide of 6ANI serves as one half of a hydrogen bonding receptor pair. The other half of the receptor pair consists of a melamine linked to a naphthalene-1,8:4,5-bis(dicarboximide) (NI) secondary electron acceptor (MEL-NI). TREPR spectroscopy is used to probe the electronic interaction between the radicals within the photogenerated, spin-correlated radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}-. The results are compared to those obtained in earlier studies in which MeOAn-6ANI is covalently linked to NI through a 2,5-dimethylphenyl group (MeOAn-6ANI-Ph-NI). We show that the electronic coupling between the oxidized donor and reduced acceptor in the hydrogen-bonded radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}- is very similar to that of MeOAn{radical dot}+-6ANI-Ph-NI{radical dot}-.

AB - Light-driven multi-step intramolecular electron transfer in a rod-like triad, in which two of the three redox components are linked by three hydrogen bonds, was studied by time-resolved electron paramagnetic resonance (TREPR) and optical spectroscopies. One part of the molecule consists of a p-methoxyaniline primary electron donor (MeOAn) covalently linked to a 4-aminonaphthalene-1, 8-dicarboximide (6ANI) chromophoric electron acceptor (MeOAn-6ANI). The unsubstituted dicarboximide of 6ANI serves as one half of a hydrogen bonding receptor pair. The other half of the receptor pair consists of a melamine linked to a naphthalene-1,8:4,5-bis(dicarboximide) (NI) secondary electron acceptor (MEL-NI). TREPR spectroscopy is used to probe the electronic interaction between the radicals within the photogenerated, spin-correlated radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}-. The results are compared to those obtained in earlier studies in which MeOAn-6ANI is covalently linked to NI through a 2,5-dimethylphenyl group (MeOAn-6ANI-Ph-NI). We show that the electronic coupling between the oxidized donor and reduced acceptor in the hydrogen-bonded radical ion pair MeOAn{radical dot}+-6ANI/MEL-NI{radical dot}- is very similar to that of MeOAn{radical dot}+-6ANI-Ph-NI{radical dot}-.

KW - Electron paramagnetic resonance

KW - Electron transfer

KW - Photochemistry

KW - Radical pairs

UR - http://www.scopus.com/inward/record.url?scp=33646266484&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646266484&partnerID=8YFLogxK

U2 - 10.1016/j.chemphys.2005.11.044

DO - 10.1016/j.chemphys.2005.11.044

M3 - Article

AN - SCOPUS:33646266484

VL - 324

SP - 63

EP - 71

JO - Chemical Physics

JF - Chemical Physics

SN - 0301-0104

IS - 1 SPEC. ISS.

ER -