Preparation and Solvent-dependent Photochromism of Triptycene-bonded Dithienylethenes

Luo, Qianfu; Bao, Shumin; Wang, Qiu; Qu, Da‐Hui; Liu, Changchun

doi:10.1246/cl.140499

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…Intermediate 11 and 12 were prepared according to the methods reported by Swager [25] and Chen [26], respectively. Target compound 1 and intermediate 8, 10 were prepared according to our previous work [21]. With them in hand, dithienylethene-triptycene hybrid 2 was prepared via Suzuki coupling reaction of the borate ester 9 and iodotriptycene 10 in the presence of a palladium catalyst under reflux.…”

Section: Synthesismentioning

confidence: 99%

Photochromic dithienylethene-branched triptycene hybrids

et al. 2015

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Section: Synthesismentioning

confidence: 99%

Photochromic dithienylethene-branched triptycene hybrids

et al. 2015

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“…Moreover, a third component, a commercial diarylethene (DAE), could be added to the gel to modulate the CPL as a photoisomerization unit. DAE is a type of a well-researched photochromic molecule, in which the achromatous (nonconjugated) ring-open state changes to the colored ring-closed state with the irradiation of UV light and returns back to the ring-open state upon exposure to visible light. − Considering that the emission band of RhB or DCF is overlapped with the adsorption band of the ring-closed state of DAE, the Förster resonance energy transfer (FRET) effect − is expected to happen from RhB or DCF to the closed state of DAE in supramolecular assemblies and lead to the emission quenching. Subsequently, by irradiating with visible light, the ring-open state of DAE can break the FRET effect and recover the emission of RhB or DCF.…”

Section: Introductionmentioning

confidence: 99%

Switchable Circularly Polarized Luminescence in Supramolecular Gels through Photomodulated FRET

Zhu

Zhang

et al. 2021

ACS Appl. Mater. Interfaces

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While the tremendous deal of efforts has been dedicated to the design and fabrication of materials with circularly polarized luminescence (CPL), the development of the chiroptical switch between different CPL signals is one of the important routes toward its application. Here, we prepared a supramolecular gel from the coassemblies containing a chiral gelator (9-fluorenmethoxycarbonyl-functionalized glutamate derivatives, FLG), a fluorescent molecule [(rhodamine B, RhB) or (2′,7′-dichlorofluorescein sodium salt, DCF)], and a photochromic molecule [1,2-bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1cyclopentene, DAE], thus constructing photomodulated switchable CPL soft materials. It was found that FLG could form supramolecular gel in ethanol and self-assemble into left-handed twisted nanostructures. During the formation of a co-gel with RhB (or DCF) and DAE, the chirality of FLG could be effectively transferred to both the fluorescent and photochromic components, which induced them with chiroptical properties including CPL and circular dichroism (CD). DAE undergoes a reversible transition between the achromatous open state and the dark purple closed state in the co-gel under alternating irradiation with UV and visible light. During such a process, an intermolecular Forster resonance energy transfer (FRET) behavior from fluorescent RhB to ring-closed DAE caused the emission quenching of RhB, which led to CPL silence of RhB in the co-gel. Subsequent irradiation with visible light caused the restoration of the emission and CPL activity with the restored open state. These changes could be repeated many times upon alternate UV and visible irradiation. Therefore, a reversible CPL switch was fabricated in supramolecular gels through the photomodulated FRET process.

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