Photoinduced electron transfer in self-assembled dimers of 3-fold symmetric donor-acceptor molecules based on perylene-3,4: 9,10-bis(dicarboximide)

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Abstract

The influence of π-stacking on photoinduced electron transfer in a series of donor-acceptor molecules attached to a 3-fold symmetric scaffold was studied. The donor-acceptor unit is a DEA-PDI pair (DEA = N,N-diethylaniline; PDI = perylene-3,4:9,10-bis(dicarboximide)), in which the 4-position of DEA is covalently attached to the nitrogen atom of one imide of PDI. One, two, or three DEA-PDI units are attached to the para position of one of the phenyl groups of 1,3,5-triphenylbenzene, using the other PDI imide group to form mono-, bis-, and tris(DEA-PDI). These molecules demonstrate an increasing tendency to self-assemble into π-stacked dimers in solution in the order mono(DEA-PDI) ≪bis(DEA-PDI) <tris(DEA-PDI). Photoinduced electron transfer in both the monomers and self-assembled dimers was studied by femtosecond transient absorption spectroscopy. The charge separation (CS) and charge recombination time (CR) constants are found to be independent of π-stacking aptitudes, while the transient spectral features differ significantly upon dimerization. The electronic interactions imposed by π-stacking appear to change the energies of the ground, excited, and ionic states of DEA-PDI to a similar extent, which results in similar energies for CS and CR within the monomers and dimers.

Original languageEnglish
Pages (from-to)7497-7505
Number of pages9
JournalJournal of Physical Chemistry A
Volume108
Issue number37
DOIs
Publication statusPublished - Sep 16 2004

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Perylene
Dimers
Imides
electron transfer
imides
dimers
polarization (charge separation)
Molecules
Electrons
monomers
Monomers
aptitude
molecules
Dimerization
dimerization
Absorption spectroscopy
Scaffolds
nitrogen atoms
time constant
absorption spectroscopy

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

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title = "Photoinduced electron transfer in self-assembled dimers of 3-fold symmetric donor-acceptor molecules based on perylene-3,4: 9,10-bis(dicarboximide)",
abstract = "The influence of π-stacking on photoinduced electron transfer in a series of donor-acceptor molecules attached to a 3-fold symmetric scaffold was studied. The donor-acceptor unit is a DEA-PDI pair (DEA = N,N-diethylaniline; PDI = perylene-3,4:9,10-bis(dicarboximide)), in which the 4-position of DEA is covalently attached to the nitrogen atom of one imide of PDI. One, two, or three DEA-PDI units are attached to the para position of one of the phenyl groups of 1,3,5-triphenylbenzene, using the other PDI imide group to form mono-, bis-, and tris(DEA-PDI). These molecules demonstrate an increasing tendency to self-assemble into π-stacked dimers in solution in the order mono(DEA-PDI) ≪bis(DEA-PDI)",
author = "Boris Rybtchinski and Sinks, {Louise E.} and Wasielewski, {Michael R}",
year = "2004",
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T1 - Photoinduced electron transfer in self-assembled dimers of 3-fold symmetric donor-acceptor molecules based on perylene-3,4

T2 - 9,10-bis(dicarboximide)

AU - Rybtchinski, Boris

AU - Sinks, Louise E.

AU - Wasielewski, Michael R

PY - 2004/9/16

Y1 - 2004/9/16

N2 - The influence of π-stacking on photoinduced electron transfer in a series of donor-acceptor molecules attached to a 3-fold symmetric scaffold was studied. The donor-acceptor unit is a DEA-PDI pair (DEA = N,N-diethylaniline; PDI = perylene-3,4:9,10-bis(dicarboximide)), in which the 4-position of DEA is covalently attached to the nitrogen atom of one imide of PDI. One, two, or three DEA-PDI units are attached to the para position of one of the phenyl groups of 1,3,5-triphenylbenzene, using the other PDI imide group to form mono-, bis-, and tris(DEA-PDI). These molecules demonstrate an increasing tendency to self-assemble into π-stacked dimers in solution in the order mono(DEA-PDI) ≪bis(DEA-PDI)

AB - The influence of π-stacking on photoinduced electron transfer in a series of donor-acceptor molecules attached to a 3-fold symmetric scaffold was studied. The donor-acceptor unit is a DEA-PDI pair (DEA = N,N-diethylaniline; PDI = perylene-3,4:9,10-bis(dicarboximide)), in which the 4-position of DEA is covalently attached to the nitrogen atom of one imide of PDI. One, two, or three DEA-PDI units are attached to the para position of one of the phenyl groups of 1,3,5-triphenylbenzene, using the other PDI imide group to form mono-, bis-, and tris(DEA-PDI). These molecules demonstrate an increasing tendency to self-assemble into π-stacked dimers in solution in the order mono(DEA-PDI) ≪bis(DEA-PDI)

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