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Synthesis of 3‐ethoxy‐4,4‐diisopropyl‐1,2‐dioxetanes bearing a benzo( b )furan‐2‐yl or a benzo( b )thiophen‐2‐yl group: CIEEL‐active dioxetanes emitting red light
Author(s) -
Matsumoto Masakatsu,
Hiroshima Tatsuji,
Chiba Shuichi,
Isobe Ryo,
Watanabe Nobuko,
Kobayashi Hisako
Publication year - 1999
Publication title -
luminescence
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.428
H-Index - 45
eISSN - 1522-7243
pISSN - 1522-7235
DOI - 10.1002/(sici)1522-7243(199911/12)14:6<345::aid-bio559>3.0.co;2-t
Subject(s) - chemistry , benzothiophene , benzofuran , substituent , ring (chemistry) , alkoxy group , medicinal chemistry , furan , dioxetane , stereochemistry , photochemistry , chemiluminescence , thiophene , organic chemistry , alkyl
Low‐temperature singlet oxygenation of 1‐ethoxy‐2,2‐diisopropylethylenes substituted with a benzo( b )furanyl or a benzo( b )thiophenyl group bearing a t ‐butyldimethylsiloxy at the 5‐, 6‐ or 7‐position of the aromatic ring afforded the corresponding 1,2‐dioxetanes in moderate to high yields. On treatment with tetrabutylammonium fluoride in DMSO, dioxetanes with a trigger (siloxy group) at the 5‐ or 7‐position of the aromatic ring decomposed to emit red light (λ max = 615–628 nm), irrespective of the aromatic ring being benzofuran or benzothiophene. For both series of benzofuran‐analogues and benzothiophene‐analogues, an ‘odd/even’ relationship between the position of an oxyanion on the aromatic ring relative to the attachment point to the dioxetane and the chemiluminescent properties, λ max , Φ CL , and t 1/2 , is observed, as in the case for dioxetanes bearing a phenolic or naphtholic substituent. Copyright © 1999 John Wiley & Sons, Ltd.