Enhancing the Rate of Quantum-Dot-Photocatalyzed Carbon-Carbon Coupling by Tuning the Composition of the Dot's Ligand Shell

Zhengyi Zhang; Kedy Edme; Shichen Lian; Emily A. Weiss

doi:10.1021/jacs.6b13220

Enhancing the Rate of Quantum-Dot-Photocatalyzed Carbon-Carbon Coupling by Tuning the Composition of the Dot's Ligand Shell

Zhengyi Zhang, Kedy Edme, Shichen Lian, Emily A. Weiss

Northwestern University

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

58 Citations (Scopus)

Abstract

This Communication describes the photoredox catalysis of a C-C coupling reaction between 1-phenylpyrrolidine (PhPyr) and phenyl trans-styryl sulfone by visible-light-absorbing colloidal CdS quantum dots (QDs), without a sacrificial oxidant or reductant, and without a co-catalyst. Simple kinetic analysis reveals that photo-oxidation of PhPyr by the QDs is the rate-limiting step. Disordering of the ligand shell of the QDs by creating mixed monolayers of oleate and octylphosphonate increases the initial rate of the reaction by a factor of 2.3, and the energy efficiency (mol product/joule of incident photons) of the reaction by a factor of 1.6, by facilitating the hole-transfer step.

Original language	English
Pages (from-to)	4246-4249
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	12
DOIs	https://doi.org/10.1021/jacs.6b13220
Publication status	Published - Mar 29 2017

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Enhancing the Rate of Quantum-Dot-Photocatalyzed Carbon-Carbon Coupling by Tuning the Composition of the Dot's Ligand Shell",

abstract = "This Communication describes the photoredox catalysis of a C-C coupling reaction between 1-phenylpyrrolidine (PhPyr) and phenyl trans-styryl sulfone by visible-light-absorbing colloidal CdS quantum dots (QDs), without a sacrificial oxidant or reductant, and without a co-catalyst. Simple kinetic analysis reveals that photo-oxidation of PhPyr by the QDs is the rate-limiting step. Disordering of the ligand shell of the QDs by creating mixed monolayers of oleate and octylphosphonate increases the initial rate of the reaction by a factor of 2.3, and the energy efficiency (mol product/joule of incident photons) of the reaction by a factor of 1.6, by facilitating the hole-transfer step.",

author = "Zhengyi Zhang and Kedy Edme and Shichen Lian and Weiss, {Emily A.}",

note = "Funding Information: This research was supported as part of the Argonne-Northwestern Solar Energy Research Center, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Basic Energy Sciences, via Grant DE-SC0001059, and by the NSF through a Graduate Research Fellowship to K.E. (1324585).",

year = "2017",

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T1 - Enhancing the Rate of Quantum-Dot-Photocatalyzed Carbon-Carbon Coupling by Tuning the Composition of the Dot's Ligand Shell

AU - Zhang, Zhengyi

AU - Edme, Kedy

AU - Lian, Shichen

AU - Weiss, Emily A.

N1 - Funding Information: This research was supported as part of the Argonne-Northwestern Solar Energy Research Center, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Basic Energy Sciences, via Grant DE-SC0001059, and by the NSF through a Graduate Research Fellowship to K.E. (1324585).

PY - 2017/3/29

Y1 - 2017/3/29

N2 - This Communication describes the photoredox catalysis of a C-C coupling reaction between 1-phenylpyrrolidine (PhPyr) and phenyl trans-styryl sulfone by visible-light-absorbing colloidal CdS quantum dots (QDs), without a sacrificial oxidant or reductant, and without a co-catalyst. Simple kinetic analysis reveals that photo-oxidation of PhPyr by the QDs is the rate-limiting step. Disordering of the ligand shell of the QDs by creating mixed monolayers of oleate and octylphosphonate increases the initial rate of the reaction by a factor of 2.3, and the energy efficiency (mol product/joule of incident photons) of the reaction by a factor of 1.6, by facilitating the hole-transfer step.

AB - This Communication describes the photoredox catalysis of a C-C coupling reaction between 1-phenylpyrrolidine (PhPyr) and phenyl trans-styryl sulfone by visible-light-absorbing colloidal CdS quantum dots (QDs), without a sacrificial oxidant or reductant, and without a co-catalyst. Simple kinetic analysis reveals that photo-oxidation of PhPyr by the QDs is the rate-limiting step. Disordering of the ligand shell of the QDs by creating mixed monolayers of oleate and octylphosphonate increases the initial rate of the reaction by a factor of 2.3, and the energy efficiency (mol product/joule of incident photons) of the reaction by a factor of 1.6, by facilitating the hole-transfer step.

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