Indeno[1,2-b]fluorene-Based [2,2]Cyclophanes with 4n/4n and 4n/[4n+2] π Electrons

Syntheses, Structural Analyses, and Excitonic Coupling Properties

Chi Shin Wang, Yu Chen Wei, Kai Hsin Chang, Pi Tai Chou, Yao-Ting Wu

Research output: Contribution to journalArticle

Abstract

Indeno[1,2-b]fluorene-based [2,2]cyclophanes with 4n/4n and 4n/[4n+2] π-electron systems were prepared, and their structures were identified by X-ray crystallography. With short π–π distances around 3.0 Å, [2.2](5,11)indeno[1,2-b]fluorenophane and its precursor [2.2](5,11)indeno[1,2-b]fluorene-6,12-dionophane exhibit remarkable transannular interactions, leading to their unusual electrochemical and photophysical properties. With the aid of femtosecond transient absorption spectroscopy, the transition from the monomeric excited state to the redshifted H-type dimeric state was first observed, correlating to the calculated excitonic energy splitting and the steady-state absorption spectra induced by charge-transfer-mediated superexchange interaction.

Original languageEnglish
Pages (from-to)10158-10162
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number30
DOIs
Publication statusPublished - 2019 Jul 22

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X ray crystallography
Electron transitions
Absorption spectroscopy
Excited states
Charge transfer
Absorption spectra
Electrons
fluorene
cyclophane 2

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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title = "Indeno[1,2-b]fluorene-Based [2,2]Cyclophanes with 4n/4n and 4n/[4n+2] π Electrons: Syntheses, Structural Analyses, and Excitonic Coupling Properties",
abstract = "Indeno[1,2-b]fluorene-based [2,2]cyclophanes with 4n/4n and 4n/[4n+2] π-electron systems were prepared, and their structures were identified by X-ray crystallography. With short π–π distances around 3.0 {\AA}, [2.2](5,11)indeno[1,2-b]fluorenophane and its precursor [2.2](5,11)indeno[1,2-b]fluorene-6,12-dionophane exhibit remarkable transannular interactions, leading to their unusual electrochemical and photophysical properties. With the aid of femtosecond transient absorption spectroscopy, the transition from the monomeric excited state to the redshifted H-type dimeric state was first observed, correlating to the calculated excitonic energy splitting and the steady-state absorption spectra induced by charge-transfer-mediated superexchange interaction.",
author = "Wang, {Chi Shin} and Wei, {Yu Chen} and Chang, {Kai Hsin} and Chou, {Pi Tai} and Yao-Ting Wu",
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journal = "Angewandte Chemie - International Edition",
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Indeno[1,2-b]fluorene-Based [2,2]Cyclophanes with 4n/4n and 4n/[4n+2] π Electrons : Syntheses, Structural Analyses, and Excitonic Coupling Properties. / Wang, Chi Shin; Wei, Yu Chen; Chang, Kai Hsin; Chou, Pi Tai; Wu, Yao-Ting.

In: Angewandte Chemie - International Edition, Vol. 58, No. 30, 22.07.2019, p. 10158-10162.

Research output: Contribution to journalArticle

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T1 - Indeno[1,2-b]fluorene-Based [2,2]Cyclophanes with 4n/4n and 4n/[4n+2] π Electrons

T2 - Syntheses, Structural Analyses, and Excitonic Coupling Properties

AU - Wang, Chi Shin

AU - Wei, Yu Chen

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AU - Chou, Pi Tai

AU - Wu, Yao-Ting

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AB - Indeno[1,2-b]fluorene-based [2,2]cyclophanes with 4n/4n and 4n/[4n+2] π-electron systems were prepared, and their structures were identified by X-ray crystallography. With short π–π distances around 3.0 Å, [2.2](5,11)indeno[1,2-b]fluorenophane and its precursor [2.2](5,11)indeno[1,2-b]fluorene-6,12-dionophane exhibit remarkable transannular interactions, leading to their unusual electrochemical and photophysical properties. With the aid of femtosecond transient absorption spectroscopy, the transition from the monomeric excited state to the redshifted H-type dimeric state was first observed, correlating to the calculated excitonic energy splitting and the steady-state absorption spectra induced by charge-transfer-mediated superexchange interaction.

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