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Cited by 119Porphyrin and Phthalocyanine ChemistryPhotochemistry and Electron Transfer StudiesPhotodynamic Therapy Research Studies

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Synthesis and Excited-State Photodynamics of Perylene−Porphyrin Dyads. 1. Parallel Energy and Charge Transfer via a Diphenylethyne Linker

Prathapan, Sreedharan, Yang, Sung Ik, Seth, Jyoti, Miller, Mark A., Bocian, David F., Holten, Dewey, Lindsey, Jonathan S.·2001·The Journal of Physical Chemistry B
DOI 10.1021/jp010335i
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Abstract

The photophysical properties of a perylene−porphyrin dyad have been examined with the aim of using this construct for molecular photonics applications. The dyad consists of a perylene-bis(imide) dye (PDI) connected to a zinc porphyrin (Zn) via a diphenylethyne linker (pep). In both polar and nonpolar solvents, the photoexcited perylene unit (PDI*) decays very rapidly (lifetimes of 2.5 (toluene) and 2.4 ps (acetonitrile)) by energy transfer to the porphyrin, forming PDI−pep−Zn* in high yield (80%, toluene; 70% acetonitrile), and hole transfer to the porphyrin, forming PDI - −pep−Zn + in lesser yield (20%, toluene; 30% acetonitrile). In both toluene and acetonitrile, the Zn* excited state subsequently decays with a lifetime of 0.4 ns primarily (80%) by electron transfer to the perylene (forming PDI - −pep−Zn + ). In the nonpolar solvent (toluene), the PDI - −pep−Zn + charge-transfer product has a lifetime of >10 ns and decays by charge recombination primarily to the ground state but also by thermal repopulation of the Zn* excited state. The occurrence of the latter process provides a direct experimental measure of the energy of the charge-separated state. In the polar solvent (acetonitrile), the PDI - −pep−Zn + charge-separated state decays much more rapidly (<0.5 ns) and exclusively to the ground state. In general, the complementary perylene and porphyrin absorption properties together with very fast and efficient PDI*−pep−Zn → PDI−pep−Zn* energy transfer suggest that perylene…

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Metadata

Authors
Prathapan, S., Yang, S. I., Seth, J., Miller, M. A., Bocian, D. F., Holten, D., & Lindsey, J. S.
Affiliations
University of California, Riverside (US)
ORCID
Venue
The Journal of Physical Chemistry B
Publisher
American Chemical Society (ACS)
Published
2001-07-31
Volume
105
Issue
34
Pages
8237-8248
ISSN
  • 1520-5207 (ISSN-L)
  • 1520-6106
DOI
10.1021/jp010335i
OpenAlex
W1997022228
Cited by
119
References
0
Citations by year
2026: 1 · 2025: 4 · 2024: 1 · 2022: 6 · 2021: 3 · 2020: 4 · 2019: 5 · 2018: 7 · 2017: 3 · 2016: 7 · 2015: 4 · 2014: 3 · 2013: 4 · 2012: 4
FWCI
4.85
Type
journal article
Language
en
Open access
closed
Locations
The Journal of Physical Chemistry B (publishedVersion)
Topics
  • Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
  • Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Photodynamic Therapy Research Studies
Keywords
zinc porphyrin, energy transfer, hole transfer, electron transfer, charge-separated states, excited-state dynamics, solvent polarity effects, charge recombination, accessory pigments, light harvesting, molecular photonics

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