Spiro-Fused Perylene Diimide Arrays

Guangpeng Gao; Ningning Liang; Hua Geng; Wei Jiang; Huiting Fu; Jiajing Feng; Jianhui Hou; Xinliang Feng; Zhaohui Wang

doi:10.1021/jacs.7b09140

Spiro-Fused Perylene Diimide Arrays

Guangpeng Gao, Ningning Liang, Hua Geng, Wei Jiang^*, Huiting Fu, Jiajing Feng, Jianhui Hou, Xinliang Feng, Zhaohui Wang

^*Corresponding author for this work

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

124 Citations (Scopus)

Abstract

The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C-H activations and 4-fold C-C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (NDP) and further π-extended spiro system (SNTP). In addition, the molecular structure of spirodiperylenetetraimide (SDP) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells.

Original language	English
Pages (from-to)	15914-15920
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	139
Issue number	44
DOIs	https://doi.org/10.1021/jacs.7b09140
Publication status	Published - 8 Nov 2017
Externally published	Yes

Access to Document

10.1021/jacs.7b09140

Cite this

@article{ec3d325494074ce29622339c9fcadb25,

title = "Spiro-Fused Perylene Diimide Arrays",

abstract = "The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C-H activations and 4-fold C-C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (NDP) and further π-extended spiro system (SNTP). In addition, the molecular structure of spirodiperylenetetraimide (SDP) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells.",

author = "Guangpeng Gao and Ningning Liang and Hua Geng and Wei Jiang and Huiting Fu and Jiajing Feng and Jianhui Hou and Xinliang Feng and Zhaohui Wang",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = nov,

day = "8",

doi = "10.1021/jacs.7b09140",

language = "English",

volume = "139",

pages = "15914--15920",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "44",

}

TY - JOUR

T1 - Spiro-Fused Perylene Diimide Arrays

AU - Gao, Guangpeng

AU - Liang, Ningning

AU - Geng, Hua

AU - Jiang, Wei

AU - Fu, Huiting

AU - Feng, Jiajing

AU - Hou, Jianhui

AU - Feng, Xinliang

AU - Wang, Zhaohui

PY - 2017/11/8

Y1 - 2017/11/8

N2 - The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C-H activations and 4-fold C-C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (NDP) and further π-extended spiro system (SNTP). In addition, the molecular structure of spirodiperylenetetraimide (SDP) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells.

AB - The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C-H activations and 4-fold C-C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (NDP) and further π-extended spiro system (SNTP). In addition, the molecular structure of spirodiperylenetetraimide (SDP) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells.

UR - http://www.scopus.com/inward/record.url?scp=85033227113&partnerID=8YFLogxK

U2 - 10.1021/jacs.7b09140

DO - 10.1021/jacs.7b09140

M3 - Article

C2 - 29057655

AN - SCOPUS:85033227113

SN - 0002-7863

VL - 139

SP - 15914

EP - 15920

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

Spiro-Fused Perylene Diimide Arrays

Abstract

Access to Document

Other files and links

Fingerprint

Cite this