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Fluoride‐ and Base‐Induced Chemiluminescence (CIEEL) of a Bifunctional Spiroacridane‐Substituted Dioxetane
Author(s) -
Adam Waldemar,
Reinhardt Dirk
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970712
Subject(s) - bifunctional , chemistry , chemiluminescence , photochemistry , dioxetane , fluoride , luminescence , amide , fluorescence , intramolecular force , thermal decomposition , phosphonium , ion , inorganic chemistry , organic chemistry , materials science , physics , optoelectronics , quantum mechanics , catalysis
The intramolecular chemically initiated electron‐exchange luminescence (CIEEL) of the novel bifunctional dioxetane 2b was studied. By selective chemical triggering, two different functionalities, namely either a phenoxy (ArO − ) or an amide (Ar 2 N − ) ion electron donor, were released, dependent on the type of triggering agent used (either base or fluoride ions). From the CIEEL quantum yields (Φ CIEEL ) for the triggered chemiluminescence and the fluorescence efficiencies (Φ Fl ) of the corresponding phenolate ( 7 ) and amide ( 5 ) emitters the singlet‐excitation yields (Φ S ) were estimated. Due to the weak fluorescence emission and the low excitation propensity, the triggerable bifunctional dioxetane 2b constitutes an inefficient CIEEL system. For comparison, the activation parameters ( E A , lg A , Δ H ≠ , Δ S ≠ ) of the direct chemiluminescence in the thermal decomposition of the dioxetane 2a were determined by standard isothermal kinetic methods.