Synthesis and fluoride-induced chemiluminescent decomposition of bicyclic dioxetanes substituted with a 2-hydroxynaphthyl group

Hoshiya, Naoyuki; Fukuda, Natsuki; Maeda, Hidetoshi; Watanabe, Nozomi; Matsumoto, Masakatsu

doi:10.1016/j.tet.2006.03.082

Cited by 23 publications

(22 citation statements)

References 13 publications

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“…However, by using the U fl s of authentic 9, we formally estimated U s for anti-7 to be 0.23 in the DMSO system and 0.17 in the acetonitrile system. These formal U s s are very close to the value of U s reported for the CTID of related bicyclic dioxetane 10 bearing a 6-hydroxynaphthalen-1-yl group (0.23 in DMSO) (Scheme 3) 23. …”

supporting

confidence: 83%

Rotamer-dependent chemiluminescence in the intramolecular charge-transfer-induced decomposition of bicyclic dioxetanes bearing a hydroxyaryl group

Matsumoto

Suzuki

Sano

et al. 2008

Tetrahedron Letters

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supporting

confidence: 83%

Rotamer-dependent chemiluminescence in the intramolecular charge-transfer-induced decomposition of bicyclic dioxetanes bearing a hydroxyaryl group

Matsumoto

Suzuki

Sano

et al. 2008

Tetrahedron Letters

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“…These precursors were synthesized through several steps starting from 7-hydroxy-2naphthyl-substituted dihydrofuran 4 (7). These precursors were synthesized through several steps starting from 7-hydroxy-2naphthyl-substituted dihydrofuran 4 (7).…”

Section: Methodsmentioning

confidence: 99%

“…These precursors were synthesized through several steps starting from 7-hydroxy-2naphthyl-substituted dihydrofuran 4 (7). For 2c, diastereomers 2c(a) and 2c(b) were separated in pure form and their stereochemistries were tentatively assigned by reference to the 1 H NMR spectral data of 1 and its related dioxetanes (7): 2c(a) possessed (RaR/SaS) form, while 2c(b) possessed (RaS/SaR) form. Hydrolysis of the ester group in 6 exclusively gave carboxylic acid 7, which was, in turn, decarboxylated with Cu 2 Cr 2 O 5 in hot quinoline to give the desired bisnaphthol 8 in 77% yield.…”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of bicyclic dioxetanes 2aÀc bearing a 2 0 -alkoxy-2hydroxy-1,1 0 -binaphthyl-7-yl moiety Dioxetanes 2a-c were prepared by singlet oxygenation of the corresponding dihydrofurans 3a-c (Scheme 1). These precursors were synthesized through several steps starting from 7-hydroxy-2naphthyl-substituted dihydrofuran 4 (7). First, oxidative cross-coupling of 4 with methyl naphthoate 5 was carried out in an O 2 /Cu 2 Cl 2 / pyridine/MeOH system at room temperature to give binaphthylsubstituted dihydrofuran 6 in 94% yield.…”

Section: Methodsmentioning

confidence: 99%

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Magnesium methoxide‐induced chemiluminescent decomposition of bicyclic dioxetanes bearing a 2′‐alkoxy‐2‐hydroxy‐1,1′‐binaphthyl‐7‐yl moiety

et al. 2012

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Bicyclic dioxetanes 2a-c bearing a 2'-alkoxy-2-hydroxy-1,1'-binaphthyl-7-yl moiety were effectively synthesized and their base-induced chemiluminescent decomposition was investigated by the use of alkaline metal (Na(+) and K(+) ) or Mg(2+) alkoxide in MeOH. When 2a-c were treated with tetrabutylammonium fluoride (TBAF) in dimethyl sulfoxide (DMSO) as a reference system, they showed chemiluminescence as a flash of orange light (maximum wavelength λmax (CL) = 573-577 nm) with efficiency Φ(CL) = 6-8 × 10(-2) . On the other hand, for an alkaline metal (Na(+) or K(+) ) alkoxide/MeOH system, 2a-c decomposed slowly to emit a glow of chemiluminescence, the spectra of which were shifted slightly toward red from the TBAF/DMSO system, and Φ(CL) (= 1.4-2.3 × 10(-3) ) was considerably decreased. In addition, Mg(OMe)2 was found to play a characteristic role as a base for the chemiluminescent decomposition of 2a-c through coordination to the intermediary oxidoaryl-substituted dioxetanes 13. Thus, Mg(2+) increased Φ(CL) to more than twice those with Na(+) or K(+) , while it shifted λmax (CL) considerably toward blue (λmax (CL) = 550-566 nm).

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“…For instance, dioxetanes bearing a 3‐oxidophenyl 2a (“ odd ”) emit light far more efficiently than do their 2‐ or 4‐oxidophenyl analogs (“ even ” pattern) 27. This phenomenon was also observed in the color change of CTICL from dioxetanes bearing a hydroxynaphthyl or its protected form 28–30. Dioxetanes with an “ odd ” pattern, 7aA , 7bA , and 7dA ( B ), decomposed to emit a longer wavelength light with higher chemiluminescence efficiency than did isomers with an “ even ” pattern 7cA ( B ), as illustrated in Figures 4 and 5.…”

Section: Structural Relationship Between Cticl‐active Dioxetanes and mentioning

confidence: 95%

Color modulation for intramolecular charge‐transfer‐induced chemiluminescence of 1,2‐dioxetanes

Matsumoto

Watanabe

Hoshiya

et al. 2008

The Chemical Record

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Dioxetanes bearing an aromatic electron donor decompose with an accompanying emission of light by an intramolecular charge-transfer-induced chemiluminescence (CTICL) mechanism. The color of the chemiluminescence from CTICL-active aryl-substituted dioxetanes is controlled by the design of the aromatic moiety and its substitution pattern, and the substituent on the carbon of the dioxetane ring. In addition to these color modulations, a change in the conformation of dioxetanes bearing a biaryl group was also found to cause a change in the color of CTICL in the coordination sphere of a crown ether complex. This new color modulation system was further developed for optically active dioxetanes bearing 2-hydroxy-1,1'-binaphthyl, the CTICL of which took place under the chiral recognition of optically active crown ether complexes. The spectra of the chemiluminescence from biaryl-type dioxetanes did not coincide with the fluorescence spectrum from the authentic emitter in the coordination sphere, but they did coincide with each other in a completely homogeneous system. This finding suggests that the emitter of CTICL possesses a transient structure, which retains the afterimage of the conformation of the dioxetane.

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Synthesis and fluoride-induced chemiluminescent decomposition of bicyclic dioxetanes substituted with a 2-hydroxynaphthyl group

Cited by 23 publications

References 13 publications

Rotamer-dependent chemiluminescence in the intramolecular charge-transfer-induced decomposition of bicyclic dioxetanes bearing a hydroxyaryl group

Rotamer-dependent chemiluminescence in the intramolecular charge-transfer-induced decomposition of bicyclic dioxetanes bearing a hydroxyaryl group

Magnesium methoxide‐induced chemiluminescent decomposition of bicyclic dioxetanes bearing a 2′‐alkoxy‐2‐hydroxy‐1,1′‐binaphthyl‐7‐yl moiety

Color modulation for intramolecular charge‐transfer‐induced chemiluminescence of 1,2‐dioxetanes

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