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Synthesis and chemiluminescent decomposition of spiro[1,2‐dioxetane‐3,6′‐benzo( c )chromene]s
Author(s) -
Matsumoto Masakatsu,
Kawahara Masao,
Watanabe Nobuko
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<341::aid-bio558>3.0.co;2-7
Subject(s) - dioxetane , chemistry , chemiluminescence , decomposition , fluoride , photochemistry , medicinal chemistry , organic chemistry , inorganic chemistry
Two spiro[1,2‐dioxetane‐3,6′‐benzo( c )chromene]s bearing a t ‐butyldimethylsiloxy as a trigger at the 10′‐ or 2′‐position were synthesized. On treatment with tetrabutylammonium fluoride in DMSO at 25°C, the 10′‐siloxyspiro[1,2‐dioxetane‐3,6′‐benzo( c )chromene] decomposed rapidly to afford a flash of blue light. The CIEEL decay of this spirochromenedioxetane was also induced by basic silica gel in hexane. By contrast, TBAF‐induced decomposition of an analogous spiro[1,2‐dioxetane‐3,6′‐benzo( c )chromene] with a trigger at the 2′‐position, resulted in emission of yellow light with very low efficiency. Copyright © 1999 John Wiley & Sons, Ltd.