Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for efficient OPV non-fullerene acceptors

Xiangchun Li; Hengbin Wang; Julia A. Schneider; Zitang Wei; Wen Yong Lai; Wei Huang; Fred Wudl; Yonghao Zheng

doi:10.1039/c7tc00263g

Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for efficient OPV non-fullerene acceptors

Xiangchun Li, Hengbin Wang, Julia A. Schneider, Zitang Wei, Wen Yong Lai, Wei Huang, Fred Wudl, Yonghao Zheng

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

41 Scopus citations

Abstract

ortho-Functionalized perylene diimides (PDIs) display better electronic properties than their bay-substituted counterparts, yet their synthesis requires expensive catalysts. We report the regioselective 2,5,8,11-functionalization of PDI via the less commonly observed 1,4-addition of aryl Grignard reagents. This direct functionalization offers a simple and low-cost method to synthesize desirable ortho-substituted PDIs. Four tetraarylated PDIs are reported along with their electronic and optoelectronic properties. Preliminary organic photovoltaic devices using these molecules as non-fullerene acceptors showed good power conversion efficiencies (PCEs) up to 5%, a new record for an acceptor with a single PDI core.

Original language	English
Pages (from-to)	2781-2785
Number of pages	5
Journal	Journal of Materials Chemistry C
Volume	5
Issue number	11
DOIs	https://doi.org/10.1039/c7tc00263g
State	Published - 2017
Externally published	Yes

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title = "Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for efficient OPV non-fullerene acceptors",

abstract = "ortho-Functionalized perylene diimides (PDIs) display better electronic properties than their bay-substituted counterparts, yet their synthesis requires expensive catalysts. We report the regioselective 2,5,8,11-functionalization of PDI via the less commonly observed 1,4-addition of aryl Grignard reagents. This direct functionalization offers a simple and low-cost method to synthesize desirable ortho-substituted PDIs. Four tetraarylated PDIs are reported along with their electronic and optoelectronic properties. Preliminary organic photovoltaic devices using these molecules as non-fullerene acceptors showed good power conversion efficiencies (PCEs) up to 5%, a new record for an acceptor with a single PDI core.",

author = "Xiangchun Li and Hengbin Wang and Schneider, {Julia A.} and Zitang Wei and Lai, {Wen Yong} and Wei Huang and Fred Wudl and Yonghao Zheng",

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year = "2017",

doi = "10.1039/c7tc00263g",

language = "英语",

volume = "5",

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T1 - Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for efficient OPV non-fullerene acceptors

AU - Li, Xiangchun

AU - Wang, Hengbin

AU - Schneider, Julia A.

AU - Wei, Zitang

AU - Lai, Wen Yong

AU - Huang, Wei

AU - Wudl, Fred

AU - Zheng, Yonghao

PY - 2017

Y1 - 2017

N2 - ortho-Functionalized perylene diimides (PDIs) display better electronic properties than their bay-substituted counterparts, yet their synthesis requires expensive catalysts. We report the regioselective 2,5,8,11-functionalization of PDI via the less commonly observed 1,4-addition of aryl Grignard reagents. This direct functionalization offers a simple and low-cost method to synthesize desirable ortho-substituted PDIs. Four tetraarylated PDIs are reported along with their electronic and optoelectronic properties. Preliminary organic photovoltaic devices using these molecules as non-fullerene acceptors showed good power conversion efficiencies (PCEs) up to 5%, a new record for an acceptor with a single PDI core.

AB - ortho-Functionalized perylene diimides (PDIs) display better electronic properties than their bay-substituted counterparts, yet their synthesis requires expensive catalysts. We report the regioselective 2,5,8,11-functionalization of PDI via the less commonly observed 1,4-addition of aryl Grignard reagents. This direct functionalization offers a simple and low-cost method to synthesize desirable ortho-substituted PDIs. Four tetraarylated PDIs are reported along with their electronic and optoelectronic properties. Preliminary organic photovoltaic devices using these molecules as non-fullerene acceptors showed good power conversion efficiencies (PCEs) up to 5%, a new record for an acceptor with a single PDI core.

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M3 - 文章

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JF - Journal of Materials Chemistry C

IS - 11

ER -

Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for efficient OPV non-fullerene acceptors

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