Self-assembly-induced ultrafast photodriven charge separation in perylene-3,4-dicarboximide-based hydrogen-bonded foldamers

Kelly M. Lefler; Dick T. Co; Michael R. Wasielewski

doi:10.1021/jz3018946

Self-assembly-induced ultrafast photodriven charge separation in perylene-3,4-dicarboximide-based hydrogen-bonded foldamers

Kelly M. Lefler, Dick T. Co, Michael R. Wasielewski^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

We report the synthesis, self-assembly characteristics, and ultrafast electron transfer dynamics of a perylene-3,4-dicarboximide (PMI) covalently linked to an N,N′-bis(3,4,5-tridodecyloxyphenyl)melamine electron donor (D) via a biphenyl spacer (PMI-Ph₂-D). Synchrotron-based small- and wide-angle X-ray scattering (SAXS/WAXS) measurements in methylcyclohexane solution show that PMI-Ph₂-D self-assembles into π-π stacked, hydrogen-bonded foldamers consisting of two or three hexameric rings or helices. Ultrafast transient absorption spectroscopy reveals that photoinduced charge separation within these nanostructures occurs by a unique pathway that is emergent in the assembly, whereas electron transfer does not occur in the PMI-Ph₂-D monomers in tetrahydrofuran.

Original language	English (US)
Pages (from-to)	3798-3805
Number of pages	8
Journal	Journal of Physical Chemistry Letters
Volume	3
Issue number	24
DOIs	https://doi.org/10.1021/jz3018946
State	Published - Dec 20 2012

Keywords

Physical Processes in Nanomaterials and Nanostructures

ASJC Scopus subject areas

Materials Science(all)

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10.1021/jz3018946

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abstract = "We report the synthesis, self-assembly characteristics, and ultrafast electron transfer dynamics of a perylene-3,4-dicarboximide (PMI) covalently linked to an N,N′-bis(3,4,5-tridodecyloxyphenyl)melamine electron donor (D) via a biphenyl spacer (PMI-Ph2-D). Synchrotron-based small- and wide-angle X-ray scattering (SAXS/WAXS) measurements in methylcyclohexane solution show that PMI-Ph2-D self-assembles into π-π stacked, hydrogen-bonded foldamers consisting of two or three hexameric rings or helices. Ultrafast transient absorption spectroscopy reveals that photoinduced charge separation within these nanostructures occurs by a unique pathway that is emergent in the assembly, whereas electron transfer does not occur in the PMI-Ph2-D monomers in tetrahydrofuran.",

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AU - Co, Dick T.

AU - Wasielewski, Michael R.

PY - 2012/12/20

Y1 - 2012/12/20

N2 - We report the synthesis, self-assembly characteristics, and ultrafast electron transfer dynamics of a perylene-3,4-dicarboximide (PMI) covalently linked to an N,N′-bis(3,4,5-tridodecyloxyphenyl)melamine electron donor (D) via a biphenyl spacer (PMI-Ph2-D). Synchrotron-based small- and wide-angle X-ray scattering (SAXS/WAXS) measurements in methylcyclohexane solution show that PMI-Ph2-D self-assembles into π-π stacked, hydrogen-bonded foldamers consisting of two or three hexameric rings or helices. Ultrafast transient absorption spectroscopy reveals that photoinduced charge separation within these nanostructures occurs by a unique pathway that is emergent in the assembly, whereas electron transfer does not occur in the PMI-Ph2-D monomers in tetrahydrofuran.

AB - We report the synthesis, self-assembly characteristics, and ultrafast electron transfer dynamics of a perylene-3,4-dicarboximide (PMI) covalently linked to an N,N′-bis(3,4,5-tridodecyloxyphenyl)melamine electron donor (D) via a biphenyl spacer (PMI-Ph2-D). Synchrotron-based small- and wide-angle X-ray scattering (SAXS/WAXS) measurements in methylcyclohexane solution show that PMI-Ph2-D self-assembles into π-π stacked, hydrogen-bonded foldamers consisting of two or three hexameric rings or helices. Ultrafast transient absorption spectroscopy reveals that photoinduced charge separation within these nanostructures occurs by a unique pathway that is emergent in the assembly, whereas electron transfer does not occur in the PMI-Ph2-D monomers in tetrahydrofuran.

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Self-assembly-induced ultrafast photodriven charge separation in perylene-3,4-dicarboximide-based hydrogen-bonded foldamers

Abstract

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