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

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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.

Original languageEnglish
Pages (from-to)3798-3805
Number of pages8
JournalJournal of Physical Chemistry Letters
Volume3
Issue number24
DOIs
Publication statusPublished - Dec 20 2012

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Perylene
polarization (charge separation)
Self assembly
self assembly
Hydrogen
electron transfer
melamine
Electrons
hydrogen
tetrahydrofuran
helices
spacers
absorption spectroscopy
synchrotrons
Melamine
monomers
assembly
X ray scattering
Synchrotrons
Absorption spectroscopy

Keywords

  • Physical Processes in Nanomaterials and Nanostructures

ASJC Scopus subject areas

  • Materials Science(all)

Cite this

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AU - Wasielewski, Michael R

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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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