Altering intercomponent interactions in a photochromic multi-state [2]rotaxane

Zhang, Hui; Kou, Xin‐Xin; Zhang, Qiong; Qu, Da‐Hui; Tian, He

doi:10.1039/c1ob05307h

Cited by 59 publications

(25 citation statements)

References 36 publications

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“…The 1 H NMR spectrum of 1 in CDCl 3 is shown in Figure 1. We analyzed the 1 H NMR spectrum of 1 in comparison with our previously reported rotaxanes,14b, c, 15a, 16 and found that the BODIPY‐functionalized DB24C8 macrocycles predominately resided on the DBA recognition sites in 1 . The chemical shifts at δ =8.34, 8.05, and 7.12 ppm indicated the existence of the OPV moiety in 1 .…”

Section: Resultsmentioning

confidence: 98%

Efficient Intramolecular Energy Transfer between Two Fluorophores in a Bis‐Branched [3]Rotaxane

Yao

Hong

et al. 2014

Chemistry An Asian Journal

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A bis-branched [3]rotaxane, with two [2]rotaxane arms separated by an oligo(para-phenylenevinylene) (OPV) fluorophore, was designed and investigated. Each [2]rotaxane arm employed a difluoroboradiaza-s-indacene (BODIPY) dye-functionalized dibenzo[24]crown-8 macrocycle interlocked onto a dibenzylammonium in the rod part. The chemical structure of the [3]rotaxane was confirmed and characterized by (1)H and (13)C NMR spectroscopy and high-resolution ESI mass spectrometry. The photophysical properties of [3]rotaxane and its reference systems were investigated through UV/Vis absorption, fluorescence, and time-resolved fluorescence spectroscopy. An efficient energy-transfer process in [3]rotaxane occurred from the OPV donor to the BODIPY acceptor because of the large overlap between the absorption spectrum of the BODIPY moiety and the emission spectrum of the OPV fluorophore; this shows the important potential of this system for designing functional molecular systems.

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Section: Resultsmentioning

confidence: 98%

Efficient Intramolecular Energy Transfer between Two Fluorophores in a Bis‐Branched [3]Rotaxane

Yao

Hong

et al. 2014

Chemistry An Asian Journal

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“…Firstly, we analyzed the 1 H NMR spectra of rotaxanes 1 and 2 (Figure 1). Comparison between the 1 H NMR spectra of rotaxanes 1 and 2 and our previously synthesized rotaxanes4c, f, 5b, 7b revealed that the DB24 C8 macrocycles predominately reside on the DBA recognition sites in rotaxanes 1 and 2 . The 1 H NMR spectra (Figure 1) of [4]rotaxanes 1 and 2 showed similar patterns in CD 3 COCD 3 , with no significant differences other than the absence of the peaks of H a , H b , H c , and H d of the Fc unit in the spectrum of [4]rotaxane 2 .…”

Section: Resultsmentioning

confidence: 79%

Fluorescence Modulation in Tribranched Switchable [4]Rotaxanes

Zhang¹,

Li²,

Zhou³

et al. 2013

Chemistry A European J

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Two novel tribranched [4]rotaxanes with a 1,3,5-triphenylene core and three rotaxane arms have been designed, synthesized, and characterized by (1)H and (13)C NMR spectroscopies and HR-ESI mass spectrometry. [4]Rotaxanes 1 and 2 each possess the same three-armed skeleton. Each arm incorporates two distinguishable binding sites for a dibenzo[24]crown-8 ring, namely a dibenzylammonium site and an N-methyltriazolium site, and is terminated by a 4-morpholino-naphthalimide fluorophore as a stopper. [4]Rotaxane 1 has three di-ferrocene-functionalized dibenzo[24]crown-8 rings whereas 2 has three simple dibenzo[24]crown-8 rings interlocked with the thread component. Uniform shuttling motions of the three macrocycles in both 1 and 2 can be driven by external acid-base stimuli, which were confirmed by (1)H NMR spectroscopy. However, [4]rotaxanes 1 and 2 show distinct modes of fluorescence modulation in response to external acid-base stimuli. [4]Rotaxane 1 exhibits a remarkable fluorescence decrease in response to the addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a base, which can displace the ferrocene-functionalized macrocycle from the dibenzylammonium station to the N-methyltriazolium station. In contrast, the fluorescence intensity of [4]rotaxane 2 showed an enhancement with the addition of DBU. Time-resolved fluorescence measurements have been performed. The different photoinduced electron-transfer processes responsible for the fluorescence changes in the two molecular systems are discussed. Topological structures of this kind have significant potential for the design and construction of large and complex assemblies with controllable functions.

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“…[ 59 ] When reached the photostationary state (PSS) after irradiation for 2 min, an isosbestic point at 310 nm emerged indicated that this is a unimolecular process. [ 60 ] Reversely, when visible light ( λ > 500 nm) was imposed, the purple 1c solution returned to the original colorless solution, indicating that a photocycloreversion changed from 1c to 1o . The cyclization and cycloreversion quantum yields were measured to be 0.20 and 0.017, respectively, with 1,2‐bis(2‐methyl‐5‐phenyl‐3‐thienyl)perfluorocyclopentene as reference.…”

Section: Resultsmentioning

confidence: 99%

A novel diarylethene‐based fluorescence sensor with a benzohydrazide unit for the detection of Zn²⁺

Qiu

Cui

et al. 2020

J of Physical Organic Chem

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A novel fluorescent sensor on the basis of diarylethene and benzohydrazide unit was successfully synthesized. Its photochromic and fluorescent switching properties have been studied in detail by the irradiation of UV‐visible (UV‐Vis) lights and the stimulus of Zn2+/EDTA. The sensor exhibited high sensitivity and selectivity toward Zn2+ in tetrahydrofuran, which is not interfered by other cations, especially of congener Cd2+. The fluorescence intensity enhanced 84 times along with a 44‐nm blue shift of the emission peak after adding Zn2+. The stoichiometric ratio between the sensor and Zn2+ was 1:1, and the limit of detection (LOD) was calculated as 5.60 × 10−9 mol L−1. Besides, the sensor was applied in the detection of practical water samples with high accuracy.

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Altering intercomponent interactions in a photochromic multi-state [2]rotaxane

Cited by 59 publications

References 36 publications

Efficient Intramolecular Energy Transfer between Two Fluorophores in a Bis‐Branched [3]Rotaxane

Efficient Intramolecular Energy Transfer between Two Fluorophores in a Bis‐Branched [3]Rotaxane

Fluorescence Modulation in Tribranched Switchable [4]Rotaxanes

A novel diarylethene‐based fluorescence sensor with a benzohydrazide unit for the detection of Zn²⁺

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Altering intercomponent interactions in a photochromic multi-state [2]rotaxane

Cited by 59 publications

References 36 publications

Efficient Intramolecular Energy Transfer between Two Fluorophores in a Bis‐Branched [3]Rotaxane

Efficient Intramolecular Energy Transfer between Two Fluorophores in a Bis‐Branched [3]Rotaxane

Fluorescence Modulation in Tribranched Switchable [4]Rotaxanes

A novel diarylethene‐based fluorescence sensor with a benzohydrazide unit for the detection of Zn2+

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Product

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A novel diarylethene‐based fluorescence sensor with a benzohydrazide unit for the detection of Zn²⁺