Dendritic fullerenes (C 60 ) with photoresponsive azobenzene groups

Kay, Kwang‐Yol; Han, Ki-Jong; Yu, Yi; Park, Young Dong

doi:10.1016/s0040-4039(02)00994-2

Cited by 39 publications

(18 citation statements)

References 33 publications

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“…Azobenzene 1, 2, 5, 8 and 9 were synthesized according to a previously reported method. [16][17][18][19][20] Next, the phenolic hydroxy group on 1 and 8 was alkylated to afford 2-6 and 9, and both hydroxy groups in 1 were acetylated (7). To synthesize tetrafluoroazobenzene 8 and 9, 2,6-difluoroaniline and (4-amino-3,5difluorophenyl) methanol were converted to diazonium salt via treatment with NaNO 2 in conc.…”

Section: Resultsmentioning

confidence: 99%

Development of Photoswitchable Estrogen Receptor Ligands

Tsuchiya

Umeno

Genichiro³

et al. 2020

CHEMICAL & PHARMACEUTICAL BULLETIN

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Photopharmacology has attracted attention as an approach for the development of novel therapeutics because it allows regulation of the bioactivity of compounds based on their conformational change by photo-irradiation. Previously, we have reported several types of selective estrogen receptor (ER) modulators based on diphenylmethane skeleton. To develop novel photopharmacological reagents, we designed and synthesized a set of ER ligands based on azobenzene skeleton, which can switch its conformation following UV irradiation. Our results showed that after UV irradiation, the Z-form of the synthesized compound 9 interacted with ERα, with a K D value of 2.5 µM, whereas the E-form of compound 9 did not bind ability to ERα at 10 µM.

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Section: Resultsmentioning

confidence: 99%

Development of Photoswitchable Estrogen Receptor Ligands

Tsuchiya

Umeno

Genichiro³

et al. 2020

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…For the disubstituted malonic derivatives (9,10,11) and the fullerene C 60 -azobenzene derivatives (15,16,17) (2). The synthesis of the monosubstituted malonic ester was achieved according to the method described in the literature.…”

Section: 32mentioning

confidence: 99%

“…9 Kay et al reported the synthesis and optical properties of a novel azodendrimer bearing a fullerene C 60 unit as core. 10 Other related structures combining azobenzene-fullerene, exhibiting interesting optical properties, have been reported in the literature.…”

Section: Introductionmentioning

confidence: 98%

Synthesis, characterization and optical properties of novel dendronized azo-dyes containing a fullerene C₆₀ unit and well-defined oligo(ethylene glycol) segments

et al. 2017

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Herein, we report the preparation and characterization of a novel series of dendronized azo-dyes containing a fullerene C 60 unit and well-defined oligo(ethylene glycol) spacers. The azobenzene units present in these dyes were substituted in the 4 0 -position with different functional groups (-H, -OCH 3 , -C 4 H 9 , -CN and -NO 2 ). The optical properties of these compounds were studied by absorption spectroscopy as a function of the dipole moment of the azobenzene moieties. All fullerene C 60 -azobenzene derivatives exhibited trans-cis photoisomerization and photoprotonation under irradiation with UV-light. The results were compared to those obtained with their precursor azo-dyes without fullerene C 60 . It was found that the presence of the fullerene unit significantly quenches the photoisomerization yield, whereas the photoprotonation was not affected by the presence of this chromophore.

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“…Intense investigation has been carried out for the dendrimer with a photoisomerizable azobenzene unit 19 in the core [27][28][29] or periphery. [30][31][32] For dendrimer with a photoisomerizable azobenzene unit in the core and terminal vinyl groups in the periphery, it would be expected that simple trans-cis geometrical change of core molecule may result in the large conformational change throughout the dendritic entity and the introduction of various functional group by the reaction of terminal vinyl group could allow the easy modification of periphery.…”

Section: Introductionmentioning

confidence: 99%

Photoresponsive Arylether Dendrimers with Azobenzene Core and Terminal Vinyl Groups

Lee¹,

Choi²,

Park³

et al. 2008

Bulletin of the Korean Chemical Society

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Photoresponsive arylether dendrimers Bis-azo-Gn(3,5) 1a-1c and Bis-azo-Gn(3,4,5) 2a-2c (n = 1-3) with an azobenzene unit at the core and several vinyl groups (3,5-bis(but-3-enyloxy)phenyl groups or 3,4,5-tris(but-3-enyloxy)phenyl groups) at the periphery have been prepared. Their structures and reversible trans-cis isomerization behaviors have been investigated by 1 H-NMR, 13 C-NMR, MALDI-TOF-Mass, and UV-vis spectra. All six azobenzene-cored dendrimers carried out very fast trans → cis photoisomerization on irradiation of 350 nm light and reached to the photostationary state within 180 s. During the dark incubation, slow thermal back reversion from cis to trans form is observed for all six dendrimers and is completed within 3 days for 1a-1c and 1 day for 2a-2c. Isomerization efficiency decreases with increasing generation. However, the initial reaction rates of both trans → cis photochemical isomerization and cis → trans thermal isomerization increases significantly with increasing generation for dendrimers for 1a-1c but only slightly for 2a-2c.

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Dendritic fullerenes (C 60 ) with photoresponsive azobenzene groups

Cited by 39 publications

References 33 publications

Development of Photoswitchable Estrogen Receptor Ligands

Development of Photoswitchable Estrogen Receptor Ligands

Synthesis, characterization and optical properties of novel dendronized azo-dyes containing a fullerene C₆₀ unit and well-defined oligo(ethylene glycol) segments

Photoresponsive Arylether Dendrimers with Azobenzene Core and Terminal Vinyl Groups

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Dendritic fullerenes (C 60 ) with photoresponsive azobenzene groups

Cited by 39 publications

References 33 publications

Development of Photoswitchable Estrogen Receptor Ligands

Development of Photoswitchable Estrogen Receptor Ligands

Synthesis, characterization and optical properties of novel dendronized azo-dyes containing a fullerene C60 unit and well-defined oligo(ethylene glycol) segments

Photoresponsive Arylether Dendrimers with Azobenzene Core and Terminal Vinyl Groups

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Synthesis, characterization and optical properties of novel dendronized azo-dyes containing a fullerene C₆₀ unit and well-defined oligo(ethylene glycol) segments