Abstract
A series of linearly linked perylenediimide (PDI) dimers and trimers were synthesized in which the PDI π systems are nearly orthogonal. These oligomers and several model compounds were singly reduced, and intramolecular electron hopping between the PDI molecules was probed by electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) spectroscopy. When the functional groups attached to the ends of the oligomers were chosen to make each PDI molecule electronically equivalent, the single electron hops between the PDI molecules with rates that significantly exceed 107 s -1. Rapid electron hopping between pairs of PDI molecules having orthogonal π systems is unexpected and may expand the possible design motifs for organic electronic materials based on PDI.
| Original language | English |
|---|---|
| Pages (from-to) | 8952-8957 |
| Number of pages | 6 |
| Journal | Journal of the American Chemical Society |
| Volume | 131 |
| Issue number | 25 |
| DOIs | |
| Publication status | Published - Jul 1 2009 |
Fingerprint
ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Toward an n-type molecular wire : Electron hopping within linearly linked perylenediimide oligomers. / Wilson, Thea M.; Tauber, Michael J.; Wasielewski, Michael R.
In: Journal of the American Chemical Society, Vol. 131, No. 25, 01.07.2009, p. 8952-8957.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Toward an n-type molecular wire
T2 - Electron hopping within linearly linked perylenediimide oligomers
AU - Wilson, Thea M.
AU - Tauber, Michael J.
AU - Wasielewski, Michael R
PY - 2009/7/1
Y1 - 2009/7/1
N2 - A series of linearly linked perylenediimide (PDI) dimers and trimers were synthesized in which the PDI π systems are nearly orthogonal. These oligomers and several model compounds were singly reduced, and intramolecular electron hopping between the PDI molecules was probed by electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) spectroscopy. When the functional groups attached to the ends of the oligomers were chosen to make each PDI molecule electronically equivalent, the single electron hops between the PDI molecules with rates that significantly exceed 107 s -1. Rapid electron hopping between pairs of PDI molecules having orthogonal π systems is unexpected and may expand the possible design motifs for organic electronic materials based on PDI.
AB - A series of linearly linked perylenediimide (PDI) dimers and trimers were synthesized in which the PDI π systems are nearly orthogonal. These oligomers and several model compounds were singly reduced, and intramolecular electron hopping between the PDI molecules was probed by electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) spectroscopy. When the functional groups attached to the ends of the oligomers were chosen to make each PDI molecule electronically equivalent, the single electron hops between the PDI molecules with rates that significantly exceed 107 s -1. Rapid electron hopping between pairs of PDI molecules having orthogonal π systems is unexpected and may expand the possible design motifs for organic electronic materials based on PDI.
UR - http://www.scopus.com/inward/record.url?scp=67649592238&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=67649592238&partnerID=8YFLogxK
U2 - 10.1021/ja902258g
DO - 10.1021/ja902258g
M3 - Article
C2 - 19507855
AN - SCOPUS:67649592238
VL - 131
SP - 8952
EP - 8957
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 25
ER -