Photoinduced Electron Transfer in 2,5,8,11-Tetrakis-Donor-Substituted Perylene-3,4: 9,10-bis(dicarboximides)

Leah E. Shoer, Samuel W. Eaton, Eric A. Margulies, Michael R Wasielewski

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A series of electron donor-acceptor compounds based on substitution of perylene-3,4:9,10-bis(dicarboximide) (PDI) with four electron donors at the 2,5,8,11-positions were synthesized and characterized using femtosecond transient absorption spectroscopy. The distance between the PDI and the N,N-dimethylaniline or phenothiazine donors was varied using one or two phenyl groups. Photoexcitation of PDI results in rapid charge separation followed by charge recombination with time constants ranging from tens of picoseconds to nanoseconds. The electron transfer time constants are compared with those of the corresponding molecules in which the donor is attached to the PDI through its imide nitrogen atom. The electron transfer reactions through the 2,5,8,11-positions of PDI are generally much faster than those through the imide nitrogen positions, in concert with stronger donor electronic coupling to the PDI acceptor core and in contrast to substituents at the imide positions through which the HOMO and LUMO nodal planes pass.

Original languageEnglish
Pages (from-to)7635-7643
Number of pages9
JournalJournal of Physical Chemistry B
Volume119
Issue number24
DOIs
Publication statusPublished - Jun 18 2015

Fingerprint

Perylene
Imides
imides
electron transfer
Electrons
time constant
Nitrogen
phenothiazines
Photoexcitation
polarization (charge separation)
photoexcitation
Absorption spectroscopy
nitrogen atoms
absorption spectroscopy
electrons
Substitution reactions
substitutes
nitrogen
Atoms
Molecules

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Surfaces, Coatings and Films

Cite this

Photoinduced Electron Transfer in 2,5,8,11-Tetrakis-Donor-Substituted Perylene-3,4 : 9,10-bis(dicarboximides). / Shoer, Leah E.; Eaton, Samuel W.; Margulies, Eric A.; Wasielewski, Michael R.

In: Journal of Physical Chemistry B, Vol. 119, No. 24, 18.06.2015, p. 7635-7643.

Research output: Contribution to journalArticle

@article{87bf1cd69368499cb0bb0565826d063d,
title = "Photoinduced Electron Transfer in 2,5,8,11-Tetrakis-Donor-Substituted Perylene-3,4: 9,10-bis(dicarboximides)",
abstract = "A series of electron donor-acceptor compounds based on substitution of perylene-3,4:9,10-bis(dicarboximide) (PDI) with four electron donors at the 2,5,8,11-positions were synthesized and characterized using femtosecond transient absorption spectroscopy. The distance between the PDI and the N,N-dimethylaniline or phenothiazine donors was varied using one or two phenyl groups. Photoexcitation of PDI results in rapid charge separation followed by charge recombination with time constants ranging from tens of picoseconds to nanoseconds. The electron transfer time constants are compared with those of the corresponding molecules in which the donor is attached to the PDI through its imide nitrogen atom. The electron transfer reactions through the 2,5,8,11-positions of PDI are generally much faster than those through the imide nitrogen positions, in concert with stronger donor electronic coupling to the PDI acceptor core and in contrast to substituents at the imide positions through which the HOMO and LUMO nodal planes pass.",
author = "Shoer, {Leah E.} and Eaton, {Samuel W.} and Margulies, {Eric A.} and Wasielewski, {Michael R}",
year = "2015",
month = "6",
day = "18",
doi = "10.1021/jp511624s",
language = "English",
volume = "119",
pages = "7635--7643",
journal = "Journal of Physical Chemistry B Materials",
issn = "1520-6106",
publisher = "American Chemical Society",
number = "24",

}

TY - JOUR

T1 - Photoinduced Electron Transfer in 2,5,8,11-Tetrakis-Donor-Substituted Perylene-3,4

T2 - 9,10-bis(dicarboximides)

AU - Shoer, Leah E.

AU - Eaton, Samuel W.

AU - Margulies, Eric A.

AU - Wasielewski, Michael R

PY - 2015/6/18

Y1 - 2015/6/18

N2 - A series of electron donor-acceptor compounds based on substitution of perylene-3,4:9,10-bis(dicarboximide) (PDI) with four electron donors at the 2,5,8,11-positions were synthesized and characterized using femtosecond transient absorption spectroscopy. The distance between the PDI and the N,N-dimethylaniline or phenothiazine donors was varied using one or two phenyl groups. Photoexcitation of PDI results in rapid charge separation followed by charge recombination with time constants ranging from tens of picoseconds to nanoseconds. The electron transfer time constants are compared with those of the corresponding molecules in which the donor is attached to the PDI through its imide nitrogen atom. The electron transfer reactions through the 2,5,8,11-positions of PDI are generally much faster than those through the imide nitrogen positions, in concert with stronger donor electronic coupling to the PDI acceptor core and in contrast to substituents at the imide positions through which the HOMO and LUMO nodal planes pass.

AB - A series of electron donor-acceptor compounds based on substitution of perylene-3,4:9,10-bis(dicarboximide) (PDI) with four electron donors at the 2,5,8,11-positions were synthesized and characterized using femtosecond transient absorption spectroscopy. The distance between the PDI and the N,N-dimethylaniline or phenothiazine donors was varied using one or two phenyl groups. Photoexcitation of PDI results in rapid charge separation followed by charge recombination with time constants ranging from tens of picoseconds to nanoseconds. The electron transfer time constants are compared with those of the corresponding molecules in which the donor is attached to the PDI through its imide nitrogen atom. The electron transfer reactions through the 2,5,8,11-positions of PDI are generally much faster than those through the imide nitrogen positions, in concert with stronger donor electronic coupling to the PDI acceptor core and in contrast to substituents at the imide positions through which the HOMO and LUMO nodal planes pass.

UR - http://www.scopus.com/inward/record.url?scp=84934955265&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84934955265&partnerID=8YFLogxK

U2 - 10.1021/jp511624s

DO - 10.1021/jp511624s

M3 - Article

AN - SCOPUS:84934955265

VL - 119

SP - 7635

EP - 7643

JO - Journal of Physical Chemistry B Materials

JF - Journal of Physical Chemistry B Materials

SN - 1520-6106

IS - 24

ER -