Marked difference in singlet-chemiexcitation efficiency between syn-anti isomers of spiro[1,2-dioxetane-3,1′-dihydroisobenzofuran] for intramolecular charge-transfer-induced decomposition
✍ Scribed by Masakatsu Matsumoto; Yuka Takamido; Kana Nomura; Tamaki Shiono; Nobuko Watanabe; Hisako K. Ijuin
- Publisher
- Elsevier Science
- Year
- 2008
- Tongue
- French
- Weight
- 259 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Spiro[1,2-dioxetane-3,1 0 -dihydroisobenzofuran] syn-3 bearing a hydroxy group at the 6-position (as a model syn-rotamer of parent dioxetane 4 bearing a 3-hydroxyphenyl group) and its isomer anti-3 (as a model anti-rotamer of 4) were synthesized. When these spiro-dioxetanes were treated with tetrabutylammonium fluoride (TBAF) in DMSO, anti-3 emitted light with high efficiency (U CL = 0.41), while the respective value for syn-3 was only 1/10 for anti-3. This significant difference in U CL between syn-3 and anti-3 was attributed to the difference in their singlet-chemiexcitation efficiencies.