Organic nanosynthesis of diarylfluorene-based ladder-type gridarene isomers via intramolecular A1-B1 type Friedel-Crafts gridization

Sixian Sun; Changjin Ou; Dongqing Lin; Zongyan Zuo; Yong Yan; Ying Wei; Yuyu Liu; Linghai Xie; Wei Huang

doi:10.1016/j.tet.2018.07.047

Organic nanosynthesis of diarylfluorene-based ladder-type gridarene isomers via intramolecular A₁-B₁ type Friedel-Crafts gridization

Sixian Sun
, Changjin Ou
, Dongqing Lin
, Zongyan Zuo
, Yong Yan
, Ying Wei
, Yuyu Liu
, Linghai Xie
, Wei Huang

Institute of Flexible Electronics

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

11 Scopus citations

Abstract

Fluorene-based ladder-type nanogrids have been synthesized via the stepwise and iterative Friedel-Crafts/Suzuki cross-coupling reactions, and efficient intramolecular gridization reaction could enhance yield up to ∼95%. Multiple configurational isomers were successfully separated with the yield of 10%, 20% and 65% for Grid-DFCz-1, Grid-DFCz-2 and Grid-DFCz-3 respectively. The molecular configurations of Grid-arene isomers were characterized and confirmed by the NMR spectra. We found that molecular configuration has little influence on photophysical and electrochemical properties.

Original language	English
Pages (from-to)	5833-5838
Number of pages	6
Journal	Tetrahedron
Volume	74
Issue number	40
DOIs	https://doi.org/10.1016/j.tet.2018.07.047
State	Published - 4 Oct 2018

Keywords

Configurational isomers
Diarylfluorene
Intramolecular Friedel-Crafts reaction
Ladder-type
Solution-processed nanogrid

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10.1016/j.tet.2018.07.047

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title = "Organic nanosynthesis of diarylfluorene-based ladder-type gridarene isomers via intramolecular A1-B1 type Friedel-Crafts gridization",

abstract = "Fluorene-based ladder-type nanogrids have been synthesized via the stepwise and iterative Friedel-Crafts/Suzuki cross-coupling reactions, and efficient intramolecular gridization reaction could enhance yield up to ∼95\%. Multiple configurational isomers were successfully separated with the yield of 10\%, 20\% and 65\% for Grid-DFCz-1, Grid-DFCz-2 and Grid-DFCz-3 respectively. The molecular configurations of Grid-arene isomers were characterized and confirmed by the NMR spectra. We found that molecular configuration has little influence on photophysical and electrochemical properties.",

keywords = "Configurational isomers, Diarylfluorene, Intramolecular Friedel-Crafts reaction, Ladder-type, Solution-processed nanogrid",

author = "Sixian Sun and Changjin Ou and Dongqing Lin and Zongyan Zuo and Yong Yan and Ying Wei and Yuyu Liu and Linghai Xie and Wei Huang",

note = "Publisher Copyright: {\textcopyright} 2018",

year = "2018",

month = oct,

day = "4",

doi = "10.1016/j.tet.2018.07.047",

language = "英语",

volume = "74",

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TY - JOUR

T1 - Organic nanosynthesis of diarylfluorene-based ladder-type gridarene isomers via intramolecular A1-B1 type Friedel-Crafts gridization

AU - Sun, Sixian

AU - Ou, Changjin

AU - Lin, Dongqing

AU - Zuo, Zongyan

AU - Yan, Yong

AU - Wei, Ying

AU - Liu, Yuyu

AU - Xie, Linghai

AU - Huang, Wei

PY - 2018/10/4

Y1 - 2018/10/4

N2 - Fluorene-based ladder-type nanogrids have been synthesized via the stepwise and iterative Friedel-Crafts/Suzuki cross-coupling reactions, and efficient intramolecular gridization reaction could enhance yield up to ∼95%. Multiple configurational isomers were successfully separated with the yield of 10%, 20% and 65% for Grid-DFCz-1, Grid-DFCz-2 and Grid-DFCz-3 respectively. The molecular configurations of Grid-arene isomers were characterized and confirmed by the NMR spectra. We found that molecular configuration has little influence on photophysical and electrochemical properties.

AB - Fluorene-based ladder-type nanogrids have been synthesized via the stepwise and iterative Friedel-Crafts/Suzuki cross-coupling reactions, and efficient intramolecular gridization reaction could enhance yield up to ∼95%. Multiple configurational isomers were successfully separated with the yield of 10%, 20% and 65% for Grid-DFCz-1, Grid-DFCz-2 and Grid-DFCz-3 respectively. The molecular configurations of Grid-arene isomers were characterized and confirmed by the NMR spectra. We found that molecular configuration has little influence on photophysical and electrochemical properties.

KW - Configurational isomers

KW - Diarylfluorene

KW - Intramolecular Friedel-Crafts reaction

KW - Ladder-type

KW - Solution-processed nanogrid

UR - https://www.scopus.com/pages/publications/85053184847

U2 - 10.1016/j.tet.2018.07.047

DO - 10.1016/j.tet.2018.07.047

M3 - 文章

AN - SCOPUS:85053184847

SN - 0040-4020

VL - 74

SP - 5833

EP - 5838

JO - Tetrahedron

JF - Tetrahedron

IS - 40

ER -

Organic nanosynthesis of diarylfluorene-based ladder-type gridarene isomers via intramolecular A₁-B₁ type Friedel-Crafts gridization

Abstract

Keywords

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