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Title: Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes

Abstract

Here, cost-effective and efficient photocatalysis are highly desirable in chemical synthesis. Here we demonstrate that readily prepared suspensions of APbBr 3 (A = Cs or methylammonium (MA)) type perovskite colloids (ca. 2-100 nm) can selectively photocatalyze carbon-carbon bond formation reactions, i.e., ..alpha..-alkylations. Specifically, we demonstrate ..alpha..-alkylation of aldehydes with a turnover number (TON) of over 52,000 under visible light illumination. Hybrid organic/inorganic perovskites are revolutionizing photovoltaic research and are now impacting other research fields, but their exploration in organic synthesis is rare. Our low-cost, easy-to-process, highly efficient and bandedge-tunable perovskite photocatalyst is expected to bring new insights in chemical synthesis.

Authors:
ORCiD logo [1];  [1];  [1]; ORCiD logo [2]; ORCiD logo [1]
  1. San Diego State Univ., San Diego, CA (United States); New Jersey Institute of Technology, Newark, NJ (United States)
  2. National Renewable Energy Lab. (NREL), Golden, CO (United States)
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Center for Hybrid Organic-Inorganic Semiconductors for Energy (CHOISE); National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1490779
Report Number(s):
NREL/JA-5900-72210
Journal ID: ISSN 0002-7863
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 141; Journal Issue: 2; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
14 SOLAR ENERGY; 36 MATERIALS SCIENCE; photocatalysts; quantum dots; nanocrystals; perovskite

Citation Formats

Zhu, Xiaolin, Lin, Yixiong, Sun, Yue, Beard, Matthew C., and Yan, Yong. Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes. United States: N. p., 2019. Web. doi:10.1021/jacs.8b08720.
Zhu, Xiaolin, Lin, Yixiong, Sun, Yue, Beard, Matthew C., & Yan, Yong. Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes. United States. doi:10.1021/jacs.8b08720.
Zhu, Xiaolin, Lin, Yixiong, Sun, Yue, Beard, Matthew C., and Yan, Yong. Wed . "Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes". United States. doi:10.1021/jacs.8b08720. https://www.osti.gov/servlets/purl/1490779.
@article{osti_1490779,
title = {Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes},
author = {Zhu, Xiaolin and Lin, Yixiong and Sun, Yue and Beard, Matthew C. and Yan, Yong},
abstractNote = {Here, cost-effective and efficient photocatalysis are highly desirable in chemical synthesis. Here we demonstrate that readily prepared suspensions of APbBr3 (A = Cs or methylammonium (MA)) type perovskite colloids (ca. 2-100 nm) can selectively photocatalyze carbon-carbon bond formation reactions, i.e., ..alpha..-alkylations. Specifically, we demonstrate ..alpha..-alkylation of aldehydes with a turnover number (TON) of over 52,000 under visible light illumination. Hybrid organic/inorganic perovskites are revolutionizing photovoltaic research and are now impacting other research fields, but their exploration in organic synthesis is rare. Our low-cost, easy-to-process, highly efficient and bandedge-tunable perovskite photocatalyst is expected to bring new insights in chemical synthesis.},
doi = {10.1021/jacs.8b08720},
journal = {Journal of the American Chemical Society},
number = 2,
volume = 141,
place = {United States},
year = {2019},
month = {1}
}

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Works referencing / citing this record:

Light-Driven Intramolecular C−N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex
journal, August 2019

  • Jing, Dong; Lu, Cong; Chen, Zhuo
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  • DOI: 10.1002/anie.201906112

Hybrid benzidinium lead iodide perovskites with a 1D structure as photoinduced electron transfer photocatalysts
journal, January 2019

  • Peng, Yong; Albero, Josep; Álvarez, Eleuterio
  • Sustainable Energy & Fuels, Vol. 3, Issue 9
  • DOI: 10.1039/c9se00182d