A family of stilbene-ethers as photolabile protecting groups for primary alcohols offers controlled deprotection based on choice of wavelength

Ho, Jau Der; Lee, Ya-Wen; Chen, Ying-Zhe; Chen, Pin-Sian; Liu, Weiqi; Ding, Yi-Shun

doi:10.1016/j.tet.2013.06.074

Cited by 6 publications

(2 citation statements)

References 35 publications

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“…The literature data and our own studies ,,, indicate the promise of this phototransformation. The reaction can be used to synthesize a wide variety of polyaromatic (heteroaromatic) compounds with different functional groups .…”

Section: Introductionsupporting

confidence: 54%

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

et al. 2017

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In recent years, great synthetic potential of the photorearrangement of diarylethenes leading to naphthalene derivatives via a cascade process of photocyclization/[1,n]-H shift/cycloreversion has been demonstrated. In this work, first a multifaceted study of the influence of various factors on the efficiency of the photorearrangement of diarylethenes of furanone series containing benzene and oxazole derivatives as aryl residues has been carried out. The efficiency of this phototransformation (quantum yields) and the effect of methoxy substituents in the phenyl moiety have been studied. Despite the multistage process, the quantum yields of the photorearrangement are rather high (0.34-0.49). It has been found that the efficiency of photocyclization of diarylethenes increases with the introduction of electron-donating methoxy groups in the phenyl moiety. Using the DFT calculations, we have been able to estimate in the photoinduced isomer the distance between hydrogen atom and carbon atom to which it migrates in the result of the sigmatropic shift. For all studied diarylethenes, this value was 2.67-2.73 Å, which is less than the sum of van der Waals radii of carbon and hydrogen atoms (2.9 Å).

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Section: Introductionsupporting

confidence: 54%

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

et al. 2017

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“…It is worth noting that the transformation of furan motifs has been used for the preparation of thiophenes, however, to the best of our knowledge, the conversion of dihydrofurans into thiophenes has never been thoroughly studied and characterized.…”

Section: Introductionmentioning

confidence: 99%

A Consecutive Four‐Component Synthesis of Polysubstituted Thiophenes in Aqueous Medium

et al. 2018

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An efficient and straightforward four‐component synthesis of mono‐, bi‐ and tricyclic thiophenes from C–C + C + C + S atom fragments from 1,3‐dicarbonyl compounds, aldehydes, activated methylene halides and elemental sulfur in aqueous medium is described. Arylidene‐1,3‐dicarbonyls, N‐phenacylpyridinium bromides/N‐(p‐nitrobenzyl)pyridinium chloride, pyridinium ylides and 2,3‐dihydrofurans are believed to be the key intermediates of these consecutive transformations. This synthetic strategy provides a potential route to the construction of a library of highly substituted thiophenes with a large substrate scope in good‐to‐excellent yields.

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2-Nitrobenzyl Borate Based Photolabile Linker for Breakable Polymer Vesicles

Cheng

Chen

Liu

et al. 2016

Macromol. Rapid Commun.

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Fluorescent photolabile groups undergoing convenient synthesis and fast cleavage are being explored because of their increasing utility in both synthetic and biological chemistry. Herein, a model photosensitive poly(ethylene glycol)-lipid of NP-B-PEG with a 2-nitrobenzyl 2-pyridinylmethyl borate hydrophobic tail is synthesized. The (1) H-NMR and absorption spectra analysis of NP-B-PEG upon 365 nm irradiation in water supports a rapid photocleavage of nitrobenzyl borate with the concomitant hydrolysis of 2-pyridinylmethyl borate. It is also shown that the borate tail hydrolyzes slowly in water. Fortunately, when the polymer aqueous solution is loaded with the hydrophobic doxorubicin (DOX), the borate hydrolysis can be much retarded. The phototriggered experiment shows a two-stage DOX release: first, the slow leakage as a result of the photocleavage of 2-nitrobenzyl borate before the vesicle disintegration; second, the quick DOX precipitation from the disintegrated vesicles induced by the speeding up hydrolysis of 2-pyridinylmethyl borate.

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A family of stilbene-ethers as photolabile protecting groups for primary alcohols offers controlled deprotection based on choice of wavelength

Cited by 6 publications

References 35 publications

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

A Consecutive Four‐Component Synthesis of Polysubstituted Thiophenes in Aqueous Medium

2-Nitrobenzyl Borate Based Photolabile Linker for Breakable Polymer Vesicles

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