Synthesis, characterization, and photoinduced electron transfer properties of core-functionalized perylene-3,4: 9,10-bis(dicarboximide)s with pendant anthracenes

Shinji Ando, Charusheela Ramanan, Antonio Facchetti, Michael R Wasielewski, Tobin J Marks

Research output: Contribution to journalArticle

3 Citations (Scopus)

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 languageEnglish
Pages (from-to)19049-19057
Number of pages9
JournalJournal of Materials Chemistry
Volume21
Issue number47
DOIs
Publication statusPublished - Dec 21 2011

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Anthracenes
Perylene
Anthracene
Electron affinity
Molecules
Electrons
Anhydrides
Photoexcitation
Electrochemical properties
Absorption spectroscopy
Condensation
Thermodynamic properties
Optical properties
Oxidation
Acids

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 journalArticle

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