Synthesis and Characterizations of Bis-Spiropyran Derivatives

Lee, Sung-Min; Ji, Seungwook; Kang, Youngjong

doi:10.5012/bkcs.2012.33.11.3740

Cited by 7 publications

(7 citation statements)

References 27 publications

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“…2 and 3 were prepared in the present study by aryl homo-coupling with a palladium/indium bimetallic catalyst as described by Chang et al followed by double Fischer base condensation to the respective indolines (Scheme and Supporting Information), and characterization was consistent with earlier reports. − All chemicals for the synthesis of 2 and 3 were purchased from Aldrich or TCI and were used without further purification. High-performance liquid chromatography (HPLC) grade acetonitrile was used without additional purification for spectroscopic measurements.…”

Section: Experimental Sectionsupporting

confidence: 53%

Noncommutative Switching of Double Spiropyrans

et al. 2020

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The spiropyran family of photochromes are key components in molecular-based responsive materials and devices, e.g., as multiphotochromes, covalently coupled dyads, triads, etc. This attention is in no small part due to the change in properties that accompany the switch between spiropyran and merocyanine forms. Although the spiropyran is a single structural isomer, the merocyanine form represents a family of isomers ( TTT , TTC , CCT , etc.) and protonation states. Combining two spiropyrans into one compound increases the number of possible structures dramatically and the interaction between the units determines, which are impeded due to intramolecular quenching of excited states. Here, we show that the coupling of two spiropyran photochromes through their phenol units yields favorable interactions (crosstalk) between the components that provides access to species inaccessible with the component monospiropyran alone. Specifically, the ring opening of one spiropyran unit, which is thermally stable at −30 °C, prevents ring opening of the second spiropyran unit. Furthermore, whereas protonated E - and Z -monomerocyanines were previously shown to undergo thermal- and photo-equilibration, the corresponding protonated E - and Z - bimerocyanines are thermally stable and show one-way photoisomerization from the Z , Z - to an emissive E , E -bimerocyanine form. Subsequent deprotonation at room temperature resets the system to the bispiro ring-closed form, but deprotonation at −30 °C yields the otherwise inaccessible bimerocyanine form. This form is photochemically inert but undergoes a two-step thermal relaxation via the merocyanine-spiropyran form, showing that the connection at the phenol units provides sufficient intramolecular interaction to fine-tune the complex isomerization pathways of spiropyrans and demonstrating noncommutability in photo- and pH-regulated multistep isomerization pathways.

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Section: Experimental Sectionsupporting

confidence: 53%

Noncommutative Switching of Double Spiropyrans

et al. 2020

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“…146 A probable mechanism for the dimerisation is through coupling of radical cationic SPs generated by the oxidation by Cu(II). The related dyads 45 and 46 reported by Lee et al 147 show a new absorption band in the visible domain upon irradiation at 254 nm, though only two (not fully characterised) states are obtained in these dimers. The two compounds differ in the position of their nitro substituent and the point of attachment of the two SPs.…”

Section: Dyads Of Fulgimides Spiropyrans and Dihydropyrenesmentioning

confidence: 80%

“…Lee and coworkers also obtained a hybrid compound constituted of a central DTE and two SP units. 147 This hybrid system, 120, was synthesised as the member of a bis-SP series, the DTE being considered as a chromophore, and only two states were reported.…”

Section: Dithienylethene-based Compoundsmentioning

confidence: 99%

Multiphotochromic molecular systems

et al. 2015

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Molecular systems encompassing more than one photochromic entity can be used to build highly functional materials, thanks to their potential multi-addressability and/or multi-response properties. Over the last decade, the synthesis and spectroscopic and kinetic characterisation as well as the modeling of a wide range of multiphotochromes have been achieved in a field that is emerging as a distinct branch of photochemistry. In this review, we provide an overview of the available multiphotochromic compounds which use a variety of photoactive building blocks, e.g., diarylethene, azobenzene, spiropyran, naphthopyran or fulgimide derivatives. Their efficiency in terms of multi-responsiveness is discussed and several strategies to circumvent the most common limitation (i.e., the loss of photochromism of one part) are described.

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“…For SP222 preparation, the Sonogashira cross-coupling reaction was used to connect alkyne and aromatic halide with retaining conjugation between dithienylethene and spiropyran. It was expected that SP222 containing both spiropyran and dithienylethene moieties can be utilized for creating novel multichromic materials which exhibit metastable intermediate state other than on/off states when they are carefully combined with photo and thermal stimuli [106].…”

Section: -Sp-dyads With Fluorophores Dyes and Othersmentioning

confidence: 99%

“…Hybrid dyad SP222, containing a dithienylethene group between two spiropyran moieties was synthesized by the Sonogashira cross-coupling reaction between DTEbis-alkyne and SP61, using Pd(PPh 3 ) 4 /CuI/Et 3 N as catalyst system, dissolved in toluene/THF, with yield of 60% [106].…”

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confidence: 99%