Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Qi, Qingkai; Qian, Jingyu; Ma, Suqian; Xu, Bin; Zhang, Sean Xiao‐An; Tian, Wenjing

doi:10.1002/chem.201405426

Cited by 99 publications

(61 citation statements)

References 56 publications

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“…The MC form in CH 2 Cl 2 solution could only partly convert back to the SP form after removal of UV light and exposure to ambient light for 5 h. This indicates that CH 2 Cl 2 may have special stabilization effects for the MC form. This phenomenon has been observed in our previous work; however, the reason is still not very clear.…”

Section: Resultssupporting

confidence: 53%

“…[8] In our previousw ork, several tetraphenylethene (TPE) integratedm olecular switches wered eveloped by using ad ouble bond linkage, and high color contrastw as achieved with these fluorescent switches owing to the significant change in chemical structure. [9] As we know that the properties of molecules are greatly relatedt ot heir molecular structures and subsequent aggregation structures, [10] here we reportanew and very small tetraphenylethene-functionalized spiropyran (SP) molecular switch (FSPTPE, meaningf used SP with TPE) by sharing am utual benzene (Scheme 1), whicha chieves both emis-sion color change and on/off switching. In contrastt om ost of the reported solid-state fluorescent switches,F SPTPE only exists in an amorphous phase in the ring-closed form owing to its highlya symmetric molecular geometry and weak intermolecular interactions.…”

Section: Introductionmentioning

confidence: 97%

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A High Contrast Tri‐state Fluorescent Switch: Properties and Applications

Wang

Fang

et al. 2016

Chemistry An Asian Journal

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A high contrast tri-state fluorescent switch (FSPTPE) with both emission color change and on/off switching is achieved in a single molecular system by fusing the aggregation-induced emissive tetraphenylethene (TPE) with a molecular switch of spiropyran (SP). In contrast to most of the reported solid-state fluorescent switches, FSPTPE only exists in the amorphous phase in the ring-closed form owing to its highly asymmetric molecular geometry and weak intermolecular interactions, which leads to its grinding-inert stable cyan emission in the solid state. Such an amorphous phase facilitates the fast response of FSPTPE to acidic gases and induces the structural transition from the ring-closed form to ring-open form, accompanied with the "Off" state of the fluorescence. The structural transition leads to a planar molecular conformation and high dipole moment, which further results in strong intermolecular interactions and good crystallinity, so when the acid is added together with a solvent, both the ring-opening reaction and re-crystallization can be triggered to result in an orange emissive state. The reversible control between any two of the three states (cyan/orange/dark) can be achieved with acid/base or mechanical force/solvent treatment. Because of the stable initial state and high color contrast (Δλ=120 nm for cyan/orange switch, dark state Φ <0.01 %), the fluorescent switch is very promising for applications such as displays, chemical or mechanical sensing, and anti-counterfeiting.

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Section: Resultssupporting

confidence: 53%

Section: Introductionmentioning

confidence: 97%

A High Contrast Tri‐state Fluorescent Switch: Properties and Applications

Wang

Fang

et al. 2016

Chemistry An Asian Journal

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“…The better conjugation of the ring‐opening form of para connected SP‐TPE‐1 is critical to demonstrate the red emission. Such better conjugation had also been observed in a TPE‐SP dyad connected by a carbon–carbon double bond by Xu and Tian . In addition, the corresponding mechanochromic response of such connected SP‐TPE dyads under hydrostatic pressure was vacant.…”

Section: Introductionsupporting

confidence: 52%

“…The low fluorescence intensities remained nearly unchanged at low f w ( f w ≤60 %). This might result from the intramolecular rotation of TPE moiety, serving as relaxation channels for the excited state . However, when the water fraction in the mixed solvents was above 70 %, a dramatic blue luminescence at 495 nm was observed.…”

Section: Resultsmentioning

confidence: 99%

“…Such better conjugation had also been observedi naTPE-SP dyad connected by ac arbon-carbon double bond by Xu and Tian. [20] In addition, the corresponding mechanochromic response of such connected SP-TPE dyads under hydrostatic pressure was vacant.Therefore, our work described herein enriches as trategy to develop AIEgen based mechanochromic materials with more fantastic and obvious responses in aw ider visible spectral region and expands the mechanochromic AIE library to the areas involving externals timuli such as grinding and hydrostatic pressure.…”

Section: Introductionmentioning

confidence: 99%

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From Two, to Three, to Multi‐Color Switches: Developing AIEgen‐Based Mechanochromic Materials

Xiao

Chen

et al. 2017

ChemNanoMat

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A multi‐color switching mechanochromic aggregation‐induced emission luminogen (AIEgen) whose fluorescence spectra nearly covers the whole visible region was obtained from attaching spiropyran (SP) moiety on tetraphenylethylene (TPE). The covalent attachment of SP to TPE is crucial. It enables the tuning of the fluorescence of SP‐TPE dyads from no color change, to two‐color switching, to three‐color switching under grinding, based on the amorphization of TPE moiety and isomerization of spiropyran moiety. Under quantifiable hydrostatic pressures, the multi‐color switch with wide spectral response region was obtained resulting from distinct pressure thresholds for supramolecular and chemical structural changes. The attached spiropyran helped to enhance the response of the mechanochromic AIEgens to show more fantastic and obvious responses. The multi‐color changes and obvious responses in a wider visible region and an enhancement of fluorescence intensity give this molecule great potential for applications in visual pressure sensors, pressure calibration, etc.

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Tunable Mechanoresponsive Self‐Assembly of an Amide‐Linked Dyad with Dual Sensitivity of Photochromism and Mechanochromism

Meng

Wan

et al. 2017

Adv Funct Materials

140

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Photo-and mechanoluminescent materials that exhibit tunable emission properties when subjected to external stimuli have a wide variety of applications. However, most mechanoresponsive materials have a mechanoinduced structural transition from crystalline to amorphous phase, and there are only few reports on the crystalline to crystalline transformation. This study reports an amide-linked dyad P1 containing spiropyran and naphthalimide chromophores with dual sensitivity of photochromism and mechanochromism. Under light and mechanical stimuli, P1 performs different color transition. With mechanical force, the morphologies of P1 change from microfiber to nanosphere and the amide group in P1 plays a vital role in these transition processes. Mechanical force can induce the morphology change of P1 through enhancing π-π stacking and destroying hydrogen bonds. These results demonstrate the feasibility of the design strategy for new mechanoresponsive switching materials: both π−π stacking and hydrogen bonding of the dyad contribute the mechano-induced crystalline/crystalline transformation.

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Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Cited by 99 publications

References 56 publications

A High Contrast Tri‐state Fluorescent Switch: Properties and Applications

A High Contrast Tri‐state Fluorescent Switch: Properties and Applications

From Two, to Three, to Multi‐Color Switches: Developing AIEgen‐Based Mechanochromic Materials

Tunable Mechanoresponsive Self‐Assembly of an Amide‐Linked Dyad with Dual Sensitivity of Photochromism and Mechanochromism

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