Abstract
A series of donor-acceptor molecules consisting of core-brominated and -cyanated perylene-3,4:9,10-bis(dicarboximide) (PDI) structures covalently linked to two terminal pendant alkylanthracenes (A) is described. These hybrid molecules, having varying alkyl tether lengths as well as PDI electron affinities, were synthesized by condensation of a 1,7-dibromoperylene tetracarboxylic acid anhydride with the appropriate aminoalkylanthracene, followed by cyanation with CuCN. Thermal, optical, and electrochemical properties were characterized. PDI moiety photoexcitation results in pendant anthracene oxidation, generating 1(A+-PDI--A) species. The solution dynamics of this one-electron charge separation were characterized by ultrafast transient absorption spectroscopy, and charge separation rates are found to vary with alkyl tether length. Trends in these rates are attributed to solution phase geometric variations of the PDI-A structure, reflecting the flexibility of the spacer.
| Original language | English |
|---|---|
| Pages (from-to) | 19049-19057 |
| Number of pages | 9 |
| Journal | Journal of Materials Chemistry |
| Volume | 21 |
| Issue number | 47 |
| DOIs | |
| Publication status | Published - Dec 21 2011 |
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ASJC Scopus subject areas
- Materials Chemistry
- Chemistry(all)
Cite this
Synthesis, characterization, and photoinduced electron transfer properties of core-functionalized perylene-3,4 : 9,10-bis(dicarboximide)s with pendant anthracenes. / Ando, Shinji; Ramanan, Charusheela; Facchetti, Antonio; Wasielewski, Michael R; Marks, Tobin J.
In: Journal of Materials Chemistry, Vol. 21, No. 47, 21.12.2011, p. 19049-19057.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis, characterization, and photoinduced electron transfer properties of core-functionalized perylene-3,4
T2 - 9,10-bis(dicarboximide)s with pendant anthracenes
AU - Ando, Shinji
AU - Ramanan, Charusheela
AU - Facchetti, Antonio
AU - Wasielewski, Michael R
AU - Marks, Tobin J
PY - 2011/12/21
Y1 - 2011/12/21
N2 - A series of donor-acceptor molecules consisting of core-brominated and -cyanated perylene-3,4:9,10-bis(dicarboximide) (PDI) structures covalently linked to two terminal pendant alkylanthracenes (A) is described. These hybrid molecules, having varying alkyl tether lengths as well as PDI electron affinities, were synthesized by condensation of a 1,7-dibromoperylene tetracarboxylic acid anhydride with the appropriate aminoalkylanthracene, followed by cyanation with CuCN. Thermal, optical, and electrochemical properties were characterized. PDI moiety photoexcitation results in pendant anthracene oxidation, generating 1(A+-PDI--A) species. The solution dynamics of this one-electron charge separation were characterized by ultrafast transient absorption spectroscopy, and charge separation rates are found to vary with alkyl tether length. Trends in these rates are attributed to solution phase geometric variations of the PDI-A structure, reflecting the flexibility of the spacer.
AB - A series of donor-acceptor molecules consisting of core-brominated and -cyanated perylene-3,4:9,10-bis(dicarboximide) (PDI) structures covalently linked to two terminal pendant alkylanthracenes (A) is described. These hybrid molecules, having varying alkyl tether lengths as well as PDI electron affinities, were synthesized by condensation of a 1,7-dibromoperylene tetracarboxylic acid anhydride with the appropriate aminoalkylanthracene, followed by cyanation with CuCN. Thermal, optical, and electrochemical properties were characterized. PDI moiety photoexcitation results in pendant anthracene oxidation, generating 1(A+-PDI--A) species. The solution dynamics of this one-electron charge separation were characterized by ultrafast transient absorption spectroscopy, and charge separation rates are found to vary with alkyl tether length. Trends in these rates are attributed to solution phase geometric variations of the PDI-A structure, reflecting the flexibility of the spacer.
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UR - http://www.scopus.com/inward/citedby.url?scp=81855206309&partnerID=8YFLogxK
U2 - 10.1039/c1jm13397g
DO - 10.1039/c1jm13397g
M3 - Article
AN - SCOPUS:81855206309
VL - 21
SP - 19049
EP - 19057
JO - Journal of Materials Chemistry
JF - Journal of Materials Chemistry
SN - 0959-9428
IS - 47
ER -