Ultrafast photoinduced charge separation resulting from self-assembly of a green perylene-based dye into π-stacked arrays

Michael J. Fuller, Louise E. Sinks, Boris Rybtchinski, Jovan M. Giaimo, Xiyou Li, Michael R. Wasielewski

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54 Citations (Scopus)


Condensation of 3,4,5-tris(n-dodecyloxy)aniline with the green chromophore 1,7-bis(N-pyrrolidinyl)perylene-3,4;9,10-tetracarboxylic dianhydride yields N,N′-bis(3,4,5-tris(n-dodecyloxy)phenyl)-1,7-bis(N-pyrrolidinyl) perylene-3,4;9,10-bis(dicarboximide), 5PDI-TAP, which absorbs light strongly from 550 to 750 nm. 5PDI-TAP dissolves readily in methylcyclohexane (MCH), resulting in self-assembly into H-aggregates. Small-angle X-ray scattering data obtained on 10 -4 M solutions of 5PDI-TAP in MCH show that the aggregates are π-stacked monodisperse pentamers. Femtosecond transient absorption spectroscopy on solutions of (5PDI-TAP) 5 in MCH shows evidence of charge separation occurring with τ ≤ 150 fs between adjacent stacked members of 5PDI-TAP within the pentamer followed by charge recombination with τ = 860 ps. Transmission electron microscopy of 5PDI-TAP films cast from solution show isolated bundles of columnar aggregates. (5PDI-TAP) n is a potentially useful material for organic photovoltaics because efficient photoinduced charge generation is an intrinsic property of the assembly.

Original languageEnglish
Pages (from-to)970-975
Number of pages6
JournalJournal of Physical Chemistry A
Issue number6
Publication statusPublished - Feb 17 2005


ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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