Synthesis, characterization, physical properties, and OLED application of single BN-fused perylene diimide

Gang Li; Yongbiao Zhao; Junbo Li; Jun Cao; Jia Zhu; Xiao Wei Sun; Qichun Zhang

doi:10.1021/jo502296z

Synthesis, characterization, physical properties, and OLED application of single BN-fused perylene diimide

Gang Li, Yongbiao Zhao, Junbo Li, Jun Cao, Jia Zhu, Xiao Wei Sun^*, Qichun Zhang^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

243 Citations (Scopus)

Abstract

It is very challenging to introduce azaborine into an electrondeficient arene system because of unfavorable intramolecular electrophilic borylation reaction. In this report, we adopted a straightforward methodology to construct a large BN-embedded π-system based on perylene diimide (PDI), which is the first BN-annulation example with highly electron-withdrawing polycyclic aromatic hydrocarbons. The physical properties of the as-prepared N,N-dicyclohexyl-1-aza-12-bora-benzoperylene diimide (PDI-1BN) have been fully studied, and its sensing behavior to fluoride ion as well as its OLED performance was also investigated.

Original language	English
Pages (from-to)	196-203
Journal	Journal of Organic Chemistry
Volume	80
Issue number	1
Online published	10 Dec 2014
DOIs	https://doi.org/10.1021/jo502296z
Publication status	Published - 2 Jan 2015
Externally published	Yes

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title = "Synthesis, characterization, physical properties, and OLED application of single BN-fused perylene diimide",

abstract = "It is very challenging to introduce azaborine into an electrondeficient arene system because of unfavorable intramolecular electrophilic borylation reaction. In this report, we adopted a straightforward methodology to construct a large BN-embedded π-system based on perylene diimide (PDI), which is the first BN-annulation example with highly electron-withdrawing polycyclic aromatic hydrocarbons. The physical properties of the as-prepared N,N-dicyclohexyl-1-aza-12-bora-benzoperylene diimide (PDI-1BN) have been fully studied, and its sensing behavior to fluoride ion as well as its OLED performance was also investigated.",

author = "Gang Li and Yongbiao Zhao and Junbo Li and Jun Cao and Jia Zhu and Sun, {Xiao Wei} and Qichun Zhang",

year = "2015",

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doi = "10.1021/jo502296z",

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T1 - Synthesis, characterization, physical properties, and OLED application of single BN-fused perylene diimide

AU - Li, Gang

AU - Zhao, Yongbiao

AU - Li, Junbo

AU - Cao, Jun

AU - Zhu, Jia

AU - Sun, Xiao Wei

AU - Zhang, Qichun

PY - 2015/1/2

Y1 - 2015/1/2

N2 - It is very challenging to introduce azaborine into an electrondeficient arene system because of unfavorable intramolecular electrophilic borylation reaction. In this report, we adopted a straightforward methodology to construct a large BN-embedded π-system based on perylene diimide (PDI), which is the first BN-annulation example with highly electron-withdrawing polycyclic aromatic hydrocarbons. The physical properties of the as-prepared N,N-dicyclohexyl-1-aza-12-bora-benzoperylene diimide (PDI-1BN) have been fully studied, and its sensing behavior to fluoride ion as well as its OLED performance was also investigated.

AB - It is very challenging to introduce azaborine into an electrondeficient arene system because of unfavorable intramolecular electrophilic borylation reaction. In this report, we adopted a straightforward methodology to construct a large BN-embedded π-system based on perylene diimide (PDI), which is the first BN-annulation example with highly electron-withdrawing polycyclic aromatic hydrocarbons. The physical properties of the as-prepared N,N-dicyclohexyl-1-aza-12-bora-benzoperylene diimide (PDI-1BN) have been fully studied, and its sensing behavior to fluoride ion as well as its OLED performance was also investigated.

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U2 - 10.1021/jo502296z

DO - 10.1021/jo502296z

M3 - RGC 21 - Publication in refereed journal

SN - 0022-3263

VL - 80

SP - 196

EP - 203

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Synthesis, characterization, physical properties, and OLED application of single BN-fused perylene diimide

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