Crystallization induced enantiomer division (CIED) of π-expanded benzoacridine regioisomers

Qiang Zhao; Yihao Li; Zepeng Wang; Jianfeng Wang; Bohan Yan; Yang Yu; Jiewei Li; Jinyi Lin; Jianfeng Zhao; Jiena Weng; Xianghua Zhao; Yongqian Gao; Wei Huang

doi:10.1016/j.dyepig.2019.107616

Crystallization induced enantiomer division (CIED) of π-expanded benzoacridine regioisomers

Qiang Zhao, Yihao Li, Zepeng Wang, Jianfeng Wang, Bohan Yan, Yang Yu, Jiewei Li, Jinyi Lin, Jianfeng Zhao, Jiena Weng, Xianghua Zhao, Yongqian Gao, Wei Huang

Institute of Flexible Electronics

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

5 Scopus citations

Abstract

Asymmetrical isomerization with prochiral π-distortion is useful to precisely construct nonplanar arenes as promising wide band gap (>2.2 eV) semiconductors. A series of asymmetrical benzoacridine regioisomers (ADs) were designed and obtained via a two-step procedure including Ullmann C-N coupling, intramolecular Friedel-Crafts ortho-aroylation. Interestingly, crystallization induced enantiomer division (CIED) of four prochiral ADs was observed. The corresponding ten divided enantiomers or diastereoisomers were carefully anatomized and distinguished from their “monozygotic and/or dizygotic twins” in crystals. The precise structures of four ADs were confirmed by ¹H NMR, ¹³C NMR, HiRes MALDI-TOF MS, FT-IR and single crystal X-Ray diffraction. According to the absorbance spectra, ADs possess wide optical band gaps (2.90–2.98 eV) in film state and potential ability for high performed electronic devices.

Original language	English
Article number	107616
Journal	Dyes and Pigments
Volume	170
DOIs	https://doi.org/10.1016/j.dyepig.2019.107616
State	Published - Nov 2019

Keywords

Benzoacridine
Crystallization
Enantiomer division
Intramolecular steric distortion
π-Expansion

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10.1016/j.dyepig.2019.107616

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@article{dccc9559333147cb9b9bae6a37e5c897,

title = "Crystallization induced enantiomer division (CIED) of π-expanded benzoacridine regioisomers",

abstract = "Asymmetrical isomerization with prochiral π-distortion is useful to precisely construct nonplanar arenes as promising wide band gap (>2.2 eV) semiconductors. A series of asymmetrical benzoacridine regioisomers (ADs) were designed and obtained via a two-step procedure including Ullmann C-N coupling, intramolecular Friedel-Crafts ortho-aroylation. Interestingly, crystallization induced enantiomer division (CIED) of four prochiral ADs was observed. The corresponding ten divided enantiomers or diastereoisomers were carefully anatomized and distinguished from their “monozygotic and/or dizygotic twins” in crystals. The precise structures of four ADs were confirmed by 1H NMR, 13C NMR, HiRes MALDI-TOF MS, FT-IR and single crystal X-Ray diffraction. According to the absorbance spectra, ADs possess wide optical band gaps (2.90–2.98 eV) in film state and potential ability for high performed electronic devices.",

keywords = "Benzoacridine, Crystallization, Enantiomer division, Intramolecular steric distortion, π-Expansion",

author = "Qiang Zhao and Yihao Li and Zepeng Wang and Jianfeng Wang and Bohan Yan and Yang Yu and Jiewei Li and Jinyi Lin and Jianfeng Zhao and Jiena Weng and Xianghua Zhao and Yongqian Gao and Wei Huang",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = nov,

doi = "10.1016/j.dyepig.2019.107616",

language = "英语",

volume = "170",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Crystallization induced enantiomer division (CIED) of π-expanded benzoacridine regioisomers

AU - Zhao, Qiang

AU - Li, Yihao

AU - Wang, Zepeng

AU - Wang, Jianfeng

AU - Yan, Bohan

AU - Yu, Yang

AU - Li, Jiewei

AU - Lin, Jinyi

AU - Zhao, Jianfeng

AU - Weng, Jiena

AU - Zhao, Xianghua

AU - Gao, Yongqian

AU - Huang, Wei

PY - 2019/11

Y1 - 2019/11

N2 - Asymmetrical isomerization with prochiral π-distortion is useful to precisely construct nonplanar arenes as promising wide band gap (>2.2 eV) semiconductors. A series of asymmetrical benzoacridine regioisomers (ADs) were designed and obtained via a two-step procedure including Ullmann C-N coupling, intramolecular Friedel-Crafts ortho-aroylation. Interestingly, crystallization induced enantiomer division (CIED) of four prochiral ADs was observed. The corresponding ten divided enantiomers or diastereoisomers were carefully anatomized and distinguished from their “monozygotic and/or dizygotic twins” in crystals. The precise structures of four ADs were confirmed by 1H NMR, 13C NMR, HiRes MALDI-TOF MS, FT-IR and single crystal X-Ray diffraction. According to the absorbance spectra, ADs possess wide optical band gaps (2.90–2.98 eV) in film state and potential ability for high performed electronic devices.

AB - Asymmetrical isomerization with prochiral π-distortion is useful to precisely construct nonplanar arenes as promising wide band gap (>2.2 eV) semiconductors. A series of asymmetrical benzoacridine regioisomers (ADs) were designed and obtained via a two-step procedure including Ullmann C-N coupling, intramolecular Friedel-Crafts ortho-aroylation. Interestingly, crystallization induced enantiomer division (CIED) of four prochiral ADs was observed. The corresponding ten divided enantiomers or diastereoisomers were carefully anatomized and distinguished from their “monozygotic and/or dizygotic twins” in crystals. The precise structures of four ADs were confirmed by 1H NMR, 13C NMR, HiRes MALDI-TOF MS, FT-IR and single crystal X-Ray diffraction. According to the absorbance spectra, ADs possess wide optical band gaps (2.90–2.98 eV) in film state and potential ability for high performed electronic devices.

KW - Benzoacridine

KW - Crystallization

KW - Enantiomer division

KW - Intramolecular steric distortion

KW - π-Expansion

UR - http://www.scopus.com/inward/record.url?scp=85067669687&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2019.107616

DO - 10.1016/j.dyepig.2019.107616

M3 - 文章

AN - SCOPUS:85067669687

SN - 0143-7208

VL - 170

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 107616

ER -

Crystallization induced enantiomer division (CIED) of π-expanded benzoacridine regioisomers

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Keywords

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